diff --git a/packages/twenty-client-sdk/src/metadata/generated/schema.graphql b/packages/twenty-client-sdk/src/metadata/generated/schema.graphql
index 165fcdf631..4c2e06ea2b 100644
--- a/packages/twenty-client-sdk/src/metadata/generated/schema.graphql
+++ b/packages/twenty-client-sdk/src/metadata/generated/schema.graphql
@@ -2234,7 +2234,13 @@ type PublicConnectionParametersOutput {
   host: String!
   port: Float!
   username: String
-  secure: Boolean
+  connectionSecurity: EmailConnectionSecurity
+}
+
+enum EmailConnectionSecurity {
+  NONE
+  STARTTLS
+  SSL_TLS
 }
 
 type PublicImapSmtpCaldavConnectionParameters {
@@ -2589,7 +2595,7 @@ type ImapSmtpCaldavPublicConnectionParams {
   host: String!
   port: Float!
   username: String
-  secure: Boolean
+  connectionSecurity: EmailConnectionSecurity
 }
 
 type ImapSmtpCaldavPublicConnectionParameters {
@@ -4546,7 +4552,7 @@ input ConnectionParametersInput {
   port: Float!
   username: String
   password: String
-  secure: Boolean
+  connectionSecurity: EmailConnectionSecurity
 }
 
 input UpdateLabPublicFeatureFlagInput {
diff --git a/packages/twenty-client-sdk/src/metadata/generated/schema.ts b/packages/twenty-client-sdk/src/metadata/generated/schema.ts
index 1801d53bfe..6f0727d870 100644
--- a/packages/twenty-client-sdk/src/metadata/generated/schema.ts
+++ b/packages/twenty-client-sdk/src/metadata/generated/schema.ts
@@ -1878,10 +1878,12 @@ export interface PublicConnectionParametersOutput {
     host: Scalars['String']
     port: Scalars['Float']
     username?: Scalars['String']
-    secure?: Scalars['Boolean']
+    connectionSecurity?: EmailConnectionSecurity
     __typename: 'PublicConnectionParametersOutput'
 }
 
+export type EmailConnectionSecurity = 'NONE' | 'STARTTLS' | 'SSL_TLS'
+
 export interface PublicImapSmtpCaldavConnectionParameters {
     IMAP?: PublicConnectionParametersOutput
     SMTP?: PublicConnectionParametersOutput
@@ -2235,7 +2237,7 @@ export interface ImapSmtpCaldavPublicConnectionParams {
     host: Scalars['String']
     port: Scalars['Float']
     username?: Scalars['String']
-    secure?: Scalars['Boolean']
+    connectionSecurity?: EmailConnectionSecurity
     __typename: 'ImapSmtpCaldavPublicConnectionParams'
 }
 
@@ -4934,7 +4936,7 @@ export interface PublicConnectionParametersOutputGenqlSelection{
     host?: boolean | number
     port?: boolean | number
     username?: boolean | number
-    secure?: boolean | number
+    connectionSecurity?: boolean | number
     __typename?: boolean | number
     __scalar?: boolean | number
 }
@@ -5317,7 +5319,7 @@ export interface ImapSmtpCaldavPublicConnectionParamsGenqlSelection{
     host?: boolean | number
     port?: boolean | number
     username?: boolean | number
-    secure?: boolean | number
+    connectionSecurity?: boolean | number
     __typename?: boolean | number
     __scalar?: boolean | number
 }
@@ -6476,7 +6478,7 @@ export interface SendEmailAttachmentInput {id: Scalars['String'],name: Scalars['
 
 export interface EmailAccountConnectionParameters {IMAP?: (ConnectionParametersInput | null),SMTP?: (ConnectionParametersInput | null),CALDAV?: (ConnectionParametersInput | null)}
 
-export interface ConnectionParametersInput {host: Scalars['String'],port: Scalars['Float'],username?: (Scalars['String'] | null),password?: (Scalars['String'] | null),secure?: (Scalars['Boolean'] | null)}
+export interface ConnectionParametersInput {host: Scalars['String'],port: Scalars['Float'],username?: (Scalars['String'] | null),password?: (Scalars['String'] | null),connectionSecurity?: (EmailConnectionSecurity | null)}
 
 export interface UpdateLabPublicFeatureFlagInput {publicFeatureFlag: Scalars['String'],value: Scalars['Boolean']}
 
@@ -9027,6 +9029,12 @@ export const enumBillingEntitlementKey = {
    AUDIT_LOGS: 'AUDIT_LOGS' as const
 }
 
+export const enumEmailConnectionSecurity = {
+   NONE: 'NONE' as const,
+   STARTTLS: 'STARTTLS' as const,
+   SSL_TLS: 'SSL_TLS' as const
+}
+
 export const enumEmailingDomainStatus = {
    PENDING: 'PENDING' as const,
    VERIFIED: 'VERIFIED' as const,
diff --git a/packages/twenty-client-sdk/src/metadata/generated/types.ts b/packages/twenty-client-sdk/src/metadata/generated/types.ts
index 37c4461820..06d7741a98 100644
--- a/packages/twenty-client-sdk/src/metadata/generated/types.ts
+++ b/packages/twenty-client-sdk/src/metadata/generated/types.ts
@@ -61,27 +61,28 @@ export default {
         202,
         217,
         229,
-        268,
-        270,
+        235,
+        269,
         271,
         272,
         273,
         274,
         275,
         276,
-        283,
-        321,
+        277,
+        284,
         322,
         323,
         324,
-        326,
-        328,
-        339,
-        346,
-        353,
-        475,
-        480,
-        488
+        325,
+        327,
+        329,
+        340,
+        347,
+        354,
+        476,
+        481,
+        489
     ],
     "types": {
         "BillingProductDTO": {
@@ -4348,13 +4349,14 @@ export default {
             "username": [
                 1
             ],
-            "secure": [
-                6
+            "connectionSecurity": [
+                235
             ],
             "__typename": [
                 1
             ]
         },
+        "EmailConnectionSecurity": {},
         "PublicImapSmtpCaldavConnectionParameters": {
             "IMAP": [
                 234
@@ -4419,7 +4421,7 @@ export default {
                 4
             ],
             "connectionParameters": [
-                235
+                236
             ],
             "__typename": [
                 1
@@ -4470,7 +4472,7 @@ export default {
         },
         "AvailableWorkspacesAndAccessTokens": {
             "tokens": [
-                241
+                242
             ],
             "availableWorkspaces": [
                 226
@@ -4525,7 +4527,7 @@ export default {
                 32
             ],
             "workspace": [
-                246
+                247
             ],
             "__typename": [
                 1
@@ -4574,7 +4576,7 @@ export default {
         },
         "AuthTokens": {
             "tokens": [
-                241
+                242
             ],
             "__typename": [
                 1
@@ -4615,7 +4617,7 @@ export default {
                 32
             ],
             "workspace": [
-                246
+                247
             ],
             "__typename": [
                 1
@@ -4637,7 +4639,7 @@ export default {
                 1
             ],
             "dailyUsage": [
-                257
+                258
             ],
             "__typename": [
                 1
@@ -4654,7 +4656,7 @@ export default {
                 195
             ],
             "timeSeries": [
-                257
+                258
             ],
             "periodStart": [
                 4
@@ -4663,7 +4665,7 @@ export default {
                 4
             ],
             "userDailyUsage": [
-                258
+                259
             ],
             "__typename": [
                 1
@@ -4820,10 +4822,10 @@ export default {
                 1
             ],
             "status": [
-                268
+                269
             ],
             "verificationRecords": [
-                266
+                267
             ],
             "verifiedAt": [
                 4
@@ -4838,22 +4840,22 @@ export default {
                 3
             ],
             "visibility": [
-                270
+                271
             ],
             "handle": [
                 1
             ],
             "type": [
-                271
+                272
             ],
             "isContactAutoCreationEnabled": [
                 6
             ],
             "contactAutoCreationPolicy": [
-                272
+                273
             ],
             "messageFolderImportPolicy": [
-                273
+                274
             ],
             "excludeNonProfessionalEmails": [
                 6
@@ -4862,7 +4864,7 @@ export default {
                 6
             ],
             "pendingGroupEmailsAction": [
-                274
+                275
             ],
             "isSyncEnabled": [
                 6
@@ -4871,10 +4873,10 @@ export default {
                 4
             ],
             "syncStatus": [
-                275
+                276
             ],
             "syncStage": [
-                276
+                277
             ],
             "syncStageStartedAt": [
                 4
@@ -4895,7 +4897,7 @@ export default {
                 4
             ],
             "connectedAccount": [
-                236
+                237
             ],
             "__typename": [
                 1
@@ -4910,7 +4912,7 @@ export default {
         "MessageChannelSyncStage": {},
         "CreateEmailGroupChannelOutput": {
             "messageChannel": [
-                269
+                270
             ],
             "forwardingAddress": [
                 1
@@ -4972,7 +4974,7 @@ export default {
                 21
             ],
             "skipped": [
-                280
+                281
             ],
             "__typename": [
                 1
@@ -4995,7 +4997,7 @@ export default {
                 1
             ],
             "visibility": [
-                283
+                284
             ],
             "__typename": [
                 1
@@ -5041,7 +5043,7 @@ export default {
                 1
             ],
             "location": [
-                285
+                286
             ],
             "__typename": [
                 1
@@ -5057,8 +5059,8 @@ export default {
             "username": [
                 1
             ],
-            "secure": [
-                6
+            "connectionSecurity": [
+                235
             ],
             "__typename": [
                 1
@@ -5066,13 +5068,13 @@ export default {
         },
         "ImapSmtpCaldavPublicConnectionParameters": {
             "IMAP": [
-                287
+                288
             ],
             "SMTP": [
-                287
+                288
             ],
             "CALDAV": [
-                287
+                288
             ],
             "__typename": [
                 1
@@ -5092,7 +5094,7 @@ export default {
                 3
             ],
             "connectionParameters": [
-                288
+                289
             ],
             "__typename": [
                 1
@@ -5294,7 +5296,7 @@ export default {
                 1
             ],
             "series": [
-                296
+                297
             ],
             "xAxisLabel": [
                 1
@@ -5343,7 +5345,7 @@ export default {
                 1
             ],
             "data": [
-                298
+                299
             ],
             "__typename": [
                 1
@@ -5351,7 +5353,7 @@ export default {
         },
         "LineChartData": {
             "series": [
-                299
+                300
             ],
             "xAxisLabel": [
                 1
@@ -5388,7 +5390,7 @@ export default {
         },
         "PieChartData": {
             "data": [
-                301
+                302
             ],
             "showLegend": [
                 6
@@ -5490,13 +5492,13 @@ export default {
         },
         "EventLogQueryResult": {
             "records": [
-                306
+                307
             ],
             "totalCount": [
                 21
             ],
             "pageInfo": [
-                307
+                308
             ],
             "__typename": [
                 1
@@ -5560,7 +5562,7 @@ export default {
                 1
             ],
             "parts": [
-                293
+                294
             ],
             "processedAt": [
                 4
@@ -5629,7 +5631,7 @@ export default {
         },
         "AiSystemPromptPreview": {
             "sections": [
-                312
+                313
             ],
             "estimatedTokenCount": [
                 21
@@ -5705,10 +5707,10 @@ export default {
                 3
             ],
             "evaluations": [
-                317
+                318
             ],
             "messages": [
-                310
+                311
             ],
             "createdAt": [
                 4
@@ -5739,19 +5741,19 @@ export default {
                 1
             ],
             "syncStatus": [
-                321
-            ],
-            "syncStage": [
                 322
             ],
-            "visibility": [
+            "syncStage": [
                 323
             ],
+            "visibility": [
+                324
+            ],
             "isContactAutoCreationEnabled": [
                 6
             ],
             "contactAutoCreationPolicy": [
-                324
+                325
             ],
             "isSyncEnabled": [
                 6
@@ -5802,7 +5804,7 @@ export default {
                 1
             ],
             "pendingSyncAction": [
-                326
+                327
             ],
             "messageChannelId": [
                 3
@@ -5820,7 +5822,7 @@ export default {
         "MessageFolderPendingSyncAction": {},
         "CollectionHash": {
             "collectionName": [
-                328
+                329
             ],
             "hash": [
                 1
@@ -5887,13 +5889,13 @@ export default {
         },
         "MinimalMetadata": {
             "objectMetadataItems": [
-                329
-            ],
-            "views": [
                 330
             ],
+            "views": [
+                331
+            ],
             "collectionHashes": [
-                327
+                328
             ],
             "__typename": [
                 1
@@ -6046,7 +6048,7 @@ export default {
                 2,
                 {
                     "input": [
-                        333,
+                        334,
                         "GetApiKeyInput!"
                     ]
                 }
@@ -6143,7 +6145,7 @@ export default {
                 41,
                 {
                     "input": [
-                        334,
+                        335,
                         "LogicFunctionIdInput!"
                     ]
                 }
@@ -6155,7 +6157,7 @@ export default {
                 15,
                 {
                     "input": [
-                        334,
+                        335,
                         "LogicFunctionIdInput!"
                     ]
                 }
@@ -6164,7 +6166,7 @@ export default {
                 1,
                 {
                     "input": [
-                        334,
+                        335,
                         "LogicFunctionIdInput!"
                     ]
                 }
@@ -6247,28 +6249,28 @@ export default {
                 25,
                 {
                     "input": [
-                        335,
+                        336,
                         "AgentIdInput!"
                     ]
                 }
             ],
             "previewMessageCampaignAudience": [
-                278,
+                279,
                 {
                     "input": [
-                        336,
+                        337,
                         "PreviewMessageCampaignAudienceInput!"
                     ]
                 }
             ],
             "unsubscribeTopics": [
-                282
+                283
             ],
             "unsubscribePagePreviewUrl": [
                 1
             ],
             "myMessageChannels": [
-                269,
+                270,
                 {
                     "connectedAccountId": [
                         3
@@ -6276,16 +6278,16 @@ export default {
                 }
             ],
             "getEmailingDomains": [
-                267
+                268
             ],
             "myConnectedAccounts": [
-                236
+                237
             ],
             "getRoles": [
                 29
             ],
             "getToolIndex": [
-                292
+                293
             ],
             "getToolInputSchema": [
                 15,
@@ -6297,10 +6299,10 @@ export default {
                 }
             ],
             "webhooks": [
-                291
+                292
             ],
             "webhook": [
-                291,
+                292,
                 {
                     "id": [
                         3,
@@ -6348,7 +6350,7 @@ export default {
                 }
             ],
             "myMessageFolders": [
-                325,
+                326,
                 {
                     "messageChannelId": [
                         3
@@ -6356,7 +6358,7 @@ export default {
                 }
             ],
             "myCalendarChannels": [
-                320,
+                321,
                 {
                     "connectedAccountId": [
                         3
@@ -6364,13 +6366,13 @@ export default {
                 }
             ],
             "minimalMetadata": [
-                331
+                332
             ],
             "appConnections": [
                 216,
                 {
                     "filter": [
-                        337
+                        338
                     ]
                 }
             ],
@@ -6384,13 +6386,13 @@ export default {
                 }
             ],
             "findWorkspaceAiStats": [
-                319
+                320
             ],
             "chatThreads": [
-                311
+                312
             ],
             "chatThread": [
-                311,
+                312,
                 {
                     "id": [
                         3,
@@ -6399,7 +6401,7 @@ export default {
                 }
             ],
             "chatMessages": [
-                310,
+                311,
                 {
                     "threadId": [
                         3,
@@ -6408,7 +6410,7 @@ export default {
                 }
             ],
             "chatStreamCatchupChunks": [
-                314,
+                315,
                 {
                     "threadId": [
                         3,
@@ -6417,13 +6419,13 @@ export default {
                 }
             ],
             "getAiSystemPromptPreview": [
-                313
+                314
             ],
             "skills": [
-                309
+                310
             ],
             "skill": [
-                309,
+                310,
                 {
                     "id": [
                         3,
@@ -6432,7 +6434,7 @@ export default {
                 }
             ],
             "agentTurns": [
-                318,
+                319,
                 {
                     "agentId": [
                         3,
@@ -6441,7 +6443,7 @@ export default {
                 }
             ],
             "checkUserExists": [
-                254,
+                255,
                 {
                     "email": [
                         1,
@@ -6453,7 +6455,7 @@ export default {
                 }
             ],
             "checkWorkspaceInviteHashIsValid": [
-                255,
+                256,
                 {
                     "inviteHash": [
                         1,
@@ -6471,7 +6473,7 @@ export default {
                 }
             ],
             "validatePasswordResetToken": [
-                249,
+                250,
                 {
                     "passwordResetToken": [
                         1,
@@ -6577,43 +6579,43 @@ export default {
                 222
             ],
             "eventLogs": [
-                308,
+                309,
                 {
                     "input": [
-                        338,
+                        339,
                         "EventLogQueryInput!"
                     ]
                 }
             ],
             "pieChartData": [
-                302,
+                303,
                 {
                     "input": [
-                        342,
+                        343,
                         "PieChartDataInput!"
                     ]
                 }
             ],
             "lineChartData": [
-                300,
+                301,
                 {
                     "input": [
-                        343,
+                        344,
                         "LineChartDataInput!"
                     ]
                 }
             ],
             "barChartData": [
-                297,
+                298,
                 {
                     "input": [
-                        344,
+                        345,
                         "BarChartDataInput!"
                     ]
                 }
             ],
             "getConnectedImapSmtpCaldavAccount": [
-                289,
+                290,
                 {
                     "id": [
                         3,
@@ -6622,7 +6624,7 @@ export default {
                 }
             ],
             "getAutoCompleteAddress": [
-                284,
+                285,
                 {
                     "address": [
                         1,
@@ -6641,7 +6643,7 @@ export default {
                 }
             ],
             "getAddressDetails": [
-                286,
+                287,
                 {
                     "placeId": [
                         1,
@@ -6654,21 +6656,21 @@ export default {
                 }
             ],
             "getUsageAnalytics": [
-                259,
+                260,
                 {
                     "input": [
-                        345
+                        346
                     ]
                 }
             ],
             "findManyPublicDomains": [
-                265
+                266
             ],
             "findManyMarketplaceApps": [
-                263
+                264
             ],
             "findMarketplaceAppDetail": [
-                264,
+                265,
                 {
                     "universalIdentifier": [
                         1,
@@ -6731,10 +6733,10 @@ export default {
         },
         "EventLogQueryInput": {
             "table": [
-                339
+                340
             ],
             "filters": [
-                340
+                341
             ],
             "first": [
                 21
@@ -6755,7 +6757,7 @@ export default {
                 1
             ],
             "dateRange": [
-                341
+                342
             ],
             "recordId": [
                 1
@@ -6822,7 +6824,7 @@ export default {
                 1
             ],
             "operationTypes": [
-                346
+                347
             ],
             "__typename": [
                 1
@@ -6834,7 +6836,7 @@ export default {
                 6,
                 {
                     "input": [
-                        348,
+                        349,
                         "AddQuerySubscriptionInput!"
                     ]
                 }
@@ -6843,7 +6845,7 @@ export default {
                 6,
                 {
                     "input": [
-                        349,
+                        350,
                         "RemoveQueryFromEventStreamInput!"
                     ]
                 }
@@ -6852,7 +6854,7 @@ export default {
                 158,
                 {
                     "inputs": [
-                        350,
+                        351,
                         "[CreateNavigationMenuItemInput!]!"
                     ]
                 }
@@ -6861,7 +6863,7 @@ export default {
                 158,
                 {
                     "input": [
-                        350,
+                        351,
                         "CreateNavigationMenuItemInput!"
                     ]
                 }
@@ -6870,7 +6872,7 @@ export default {
                 158,
                 {
                     "inputs": [
-                        351,
+                        352,
                         "[UpdateOneNavigationMenuItemInput!]!"
                     ]
                 }
@@ -6879,7 +6881,7 @@ export default {
                 158,
                 {
                     "input": [
-                        351,
+                        352,
                         "UpdateOneNavigationMenuItemInput!"
                     ]
                 }
@@ -6906,7 +6908,7 @@ export default {
                 131,
                 {
                     "file": [
-                        353,
+                        354,
                         "Upload!"
                     ]
                 }
@@ -6927,7 +6929,7 @@ export default {
                 131,
                 {
                     "file": [
-                        353,
+                        354,
                         "Upload!"
                     ]
                 }
@@ -6936,7 +6938,7 @@ export default {
                 131,
                 {
                     "file": [
-                        353,
+                        354,
                         "Upload!"
                     ]
                 }
@@ -6945,7 +6947,7 @@ export default {
                 131,
                 {
                     "file": [
-                        353,
+                        354,
                         "Upload!"
                     ]
                 }
@@ -6954,7 +6956,7 @@ export default {
                 131,
                 {
                     "file": [
-                        353,
+                        354,
                         "Upload!"
                     ]
                 }
@@ -6963,7 +6965,7 @@ export default {
                 131,
                 {
                     "file": [
-                        353,
+                        354,
                         "Upload!"
                     ],
                     "fieldMetadataId": [
@@ -6976,7 +6978,7 @@ export default {
                 131,
                 {
                     "file": [
-                        353,
+                        354,
                         "Upload!"
                     ],
                     "fieldMetadataUniversalIdentifier": [
@@ -6989,7 +6991,7 @@ export default {
                 62,
                 {
                     "input": [
-                        354,
+                        355,
                         "CreateViewFilterGroupInput!"
                     ]
                 }
@@ -7002,7 +7004,7 @@ export default {
                         "String!"
                     ],
                     "input": [
-                        355,
+                        356,
                         "UpdateViewFilterGroupInput!"
                     ]
                 }
@@ -7029,7 +7031,7 @@ export default {
                 64,
                 {
                     "input": [
-                        356,
+                        357,
                         "CreateViewFilterInput!"
                     ]
                 }
@@ -7038,7 +7040,7 @@ export default {
                 64,
                 {
                     "input": [
-                        357,
+                        358,
                         "UpdateViewFilterInput!"
                     ]
                 }
@@ -7047,7 +7049,7 @@ export default {
                 64,
                 {
                     "input": [
-                        359,
+                        360,
                         "DeleteViewFilterInput!"
                     ]
                 }
@@ -7056,7 +7058,7 @@ export default {
                 64,
                 {
                     "input": [
-                        360,
+                        361,
                         "DestroyViewFilterInput!"
                     ]
                 }
@@ -7065,7 +7067,7 @@ export default {
                 70,
                 {
                     "input": [
-                        361,
+                        362,
                         "CreateViewInput!"
                     ]
                 }
@@ -7078,7 +7080,7 @@ export default {
                         "String!"
                     ],
                     "input": [
-                        362,
+                        363,
                         "UpdateViewInput!"
                     ]
                 }
@@ -7105,7 +7107,7 @@ export default {
                 70,
                 {
                     "input": [
-                        363,
+                        364,
                         "UpsertViewWidgetInput!"
                     ]
                 }
@@ -7114,7 +7116,7 @@ export default {
                 67,
                 {
                     "input": [
-                        368,
+                        369,
                         "CreateViewSortInput!"
                     ]
                 }
@@ -7123,7 +7125,7 @@ export default {
                 67,
                 {
                     "input": [
-                        369,
+                        370,
                         "UpdateViewSortInput!"
                     ]
                 }
@@ -7132,7 +7134,7 @@ export default {
                 6,
                 {
                     "input": [
-                        371,
+                        372,
                         "DeleteViewSortInput!"
                     ]
                 }
@@ -7141,7 +7143,7 @@ export default {
                 6,
                 {
                     "input": [
-                        372,
+                        373,
                         "DestroyViewSortInput!"
                     ]
                 }
@@ -7150,7 +7152,7 @@ export default {
                 60,
                 {
                     "input": [
-                        373,
+                        374,
                         "UpdateViewFieldInput!"
                     ]
                 }
@@ -7159,7 +7161,7 @@ export default {
                 60,
                 {
                     "input": [
-                        375,
+                        376,
                         "CreateViewFieldInput!"
                     ]
                 }
@@ -7168,7 +7170,7 @@ export default {
                 60,
                 {
                     "inputs": [
-                        375,
+                        376,
                         "[CreateViewFieldInput!]!"
                     ]
                 }
@@ -7177,7 +7179,7 @@ export default {
                 60,
                 {
                     "input": [
-                        376,
+                        377,
                         "DeleteViewFieldInput!"
                     ]
                 }
@@ -7186,7 +7188,7 @@ export default {
                 60,
                 {
                     "input": [
-                        377,
+                        378,
                         "DestroyViewFieldInput!"
                     ]
                 }
@@ -7195,7 +7197,7 @@ export default {
                 69,
                 {
                     "input": [
-                        378,
+                        379,
                         "UpdateViewFieldGroupInput!"
                     ]
                 }
@@ -7204,7 +7206,7 @@ export default {
                 69,
                 {
                     "input": [
-                        380,
+                        381,
                         "CreateViewFieldGroupInput!"
                     ]
                 }
@@ -7213,7 +7215,7 @@ export default {
                 69,
                 {
                     "inputs": [
-                        380,
+                        381,
                         "[CreateViewFieldGroupInput!]!"
                     ]
                 }
@@ -7222,7 +7224,7 @@ export default {
                 69,
                 {
                     "input": [
-                        381,
+                        382,
                         "DeleteViewFieldGroupInput!"
                     ]
                 }
@@ -7231,7 +7233,7 @@ export default {
                 69,
                 {
                     "input": [
-                        382,
+                        383,
                         "DestroyViewFieldGroupInput!"
                     ]
                 }
@@ -7240,7 +7242,7 @@ export default {
                 70,
                 {
                     "input": [
-                        383,
+                        384,
                         "UpsertFieldsWidgetInput!"
                     ]
                 }
@@ -7249,7 +7251,7 @@ export default {
                 2,
                 {
                     "input": [
-                        386,
+                        387,
                         "CreateApiKeyInput!"
                     ]
                 }
@@ -7258,7 +7260,7 @@ export default {
                 2,
                 {
                     "input": [
-                        387,
+                        388,
                         "UpdateApiKeyInput!"
                     ]
                 }
@@ -7267,7 +7269,7 @@ export default {
                 2,
                 {
                     "input": [
-                        388,
+                        389,
                         "RevokeApiKeyInput!"
                     ]
                 }
@@ -7389,7 +7391,7 @@ export default {
                 130,
                 {
                     "input": [
-                        389,
+                        390,
                         "CreateApprovedAccessDomainInput!"
                     ]
                 }
@@ -7398,7 +7400,7 @@ export default {
                 6,
                 {
                     "input": [
-                        390,
+                        391,
                         "DeleteApprovedAccessDomainInput!"
                     ]
                 }
@@ -7407,7 +7409,7 @@ export default {
                 130,
                 {
                     "input": [
-                        391,
+                        392,
                         "ValidateApprovedAccessDomainInput!"
                     ]
                 }
@@ -7416,7 +7418,7 @@ export default {
                 123,
                 {
                     "input": [
-                        392,
+                        393,
                         "CreatePageLayoutTabInput!"
                     ]
                 }
@@ -7429,7 +7431,7 @@ export default {
                         "String!"
                     ],
                     "input": [
-                        393,
+                        394,
                         "UpdatePageLayoutTabInput!"
                     ]
                 }
@@ -7447,7 +7449,7 @@ export default {
                 124,
                 {
                     "input": [
-                        394,
+                        395,
                         "CreatePageLayoutInput!"
                     ]
                 }
@@ -7460,7 +7462,7 @@ export default {
                         "String!"
                     ],
                     "input": [
-                        395,
+                        396,
                         "UpdatePageLayoutInput!"
                     ]
                 }
@@ -7482,7 +7484,7 @@ export default {
                         "String!"
                     ],
                     "input": [
-                        396,
+                        397,
                         "UpdatePageLayoutWithTabsInput!"
                     ]
                 }
@@ -7518,7 +7520,7 @@ export default {
                 85,
                 {
                     "input": [
-                        400,
+                        401,
                         "CreatePageLayoutWidgetInput!"
                     ]
                 }
@@ -7531,7 +7533,7 @@ export default {
                         "String!"
                     ],
                     "input": [
-                        401,
+                        402,
                         "UpdatePageLayoutWidgetInput!"
                     ]
                 }
@@ -7549,7 +7551,7 @@ export default {
                 41,
                 {
                     "input": [
-                        334,
+                        335,
                         "LogicFunctionIdInput!"
                     ]
                 }
@@ -7558,7 +7560,7 @@ export default {
                 41,
                 {
                     "input": [
-                        402,
+                        403,
                         "CreateLogicFunctionFromSourceInput!"
                     ]
                 }
@@ -7567,7 +7569,7 @@ export default {
                 167,
                 {
                     "input": [
-                        403,
+                        404,
                         "ExecuteOneLogicFunctionInput!"
                     ]
                 }
@@ -7576,7 +7578,7 @@ export default {
                 6,
                 {
                     "input": [
-                        404,
+                        405,
                         "UpdateLogicFunctionFromSourceInput!"
                     ]
                 }
@@ -7585,7 +7587,7 @@ export default {
                 35,
                 {
                     "input": [
-                        406,
+                        407,
                         "CreateCommandMenuItemInput!"
                     ]
                 }
@@ -7594,7 +7596,7 @@ export default {
                 35,
                 {
                     "input": [
-                        407,
+                        408,
                         "UpdateCommandMenuItemInput!"
                     ]
                 }
@@ -7621,7 +7623,7 @@ export default {
                 34,
                 {
                     "input": [
-                        408,
+                        409,
                         "CreateFrontComponentInput!"
                     ]
                 }
@@ -7630,7 +7632,7 @@ export default {
                 34,
                 {
                     "input": [
-                        409,
+                        410,
                         "UpdateFrontComponentInput!"
                     ]
                 }
@@ -7648,7 +7650,7 @@ export default {
                 56,
                 {
                     "input": [
-                        411,
+                        412,
                         "CreateOneObjectInput!"
                     ]
                 }
@@ -7657,7 +7659,7 @@ export default {
                 56,
                 {
                     "input": [
-                        413,
+                        414,
                         "DeleteOneObjectInput!"
                     ]
                 }
@@ -7666,7 +7668,7 @@ export default {
                 56,
                 {
                     "input": [
-                        414,
+                        415,
                         "UpdateOneObjectInput!"
                     ]
                 }
@@ -7675,7 +7677,7 @@ export default {
                 47,
                 {
                     "input": [
-                        416,
+                        417,
                         "CreateOneIndexInput!"
                     ]
                 }
@@ -7684,7 +7686,7 @@ export default {
                 47,
                 {
                     "input": [
-                        419,
+                        420,
                         "DeleteOneIndexInput!"
                     ]
                 }
@@ -7693,7 +7695,7 @@ export default {
                 25,
                 {
                     "input": [
-                        420,
+                        421,
                         "CreateAgentInput!"
                     ]
                 }
@@ -7702,7 +7704,7 @@ export default {
                 25,
                 {
                     "input": [
-                        421,
+                        422,
                         "UpdateAgentInput!"
                     ]
                 }
@@ -7711,43 +7713,43 @@ export default {
                 25,
                 {
                     "input": [
-                        335,
+                        336,
                         "AgentIdInput!"
                     ]
                 }
             ],
             "sendEmailViaEmailingDomain": [
-                279,
+                280,
                 {
                     "input": [
-                        422,
+                        423,
                         "SendEmailViaDomainInput!"
                     ]
                 }
             ],
             "sendMessageCampaign": [
-                281,
+                282,
                 {
                     "input": [
-                        423,
+                        424,
                         "SendMessageCampaignInput!"
                     ]
                 }
             ],
             "createUnsubscribeTopic": [
-                282,
+                283,
                 {
                     "input": [
-                        424,
+                        425,
                         "CreateUnsubscribeTopicInput!"
                     ]
                 }
             ],
             "updateUnsubscribeTopic": [
-                282,
+                283,
                 {
                     "input": [
-                        425,
+                        426,
                         "UpdateUnsubscribeTopicInput!"
                     ]
                 }
@@ -7762,25 +7764,25 @@ export default {
                 }
             ],
             "updateMessageChannel": [
-                269,
+                270,
                 {
                     "input": [
-                        426,
+                        427,
                         "UpdateMessageChannelInput!"
                     ]
                 }
             ],
             "createEmailGroupChannel": [
-                277,
+                278,
                 {
                     "input": [
-                        428,
+                        429,
                         "CreateEmailGroupChannelInput!"
                     ]
                 }
             ],
             "deleteEmailGroupChannel": [
-                269,
+                270,
                 {
                     "id": [
                         3,
@@ -7789,10 +7791,10 @@ export default {
                 }
             ],
             "createEmailingDomain": [
-                267,
+                268,
                 {
                     "input": [
-                        429,
+                        430,
                         "CreateEmailingDomainInput!"
                     ]
                 }
@@ -7807,7 +7809,7 @@ export default {
                 }
             ],
             "verifyEmailingDomain": [
-                267,
+                268,
                 {
                     "id": [
                         1,
@@ -7816,7 +7818,7 @@ export default {
                 }
             ],
             "deleteConnectedAccount": [
-                236,
+                237,
                 {
                     "id": [
                         3,
@@ -7841,7 +7843,7 @@ export default {
                 29,
                 {
                     "createRoleInput": [
-                        430,
+                        431,
                         "CreateRoleInput!"
                     ]
                 }
@@ -7850,7 +7852,7 @@ export default {
                 29,
                 {
                     "updateRoleInput": [
-                        431,
+                        432,
                         "UpdateRoleInput!"
                     ]
                 }
@@ -7868,7 +7870,7 @@ export default {
                 16,
                 {
                     "upsertObjectPermissionsInput": [
-                        433,
+                        434,
                         "UpsertObjectPermissionsInput!"
                     ]
                 }
@@ -7877,7 +7879,7 @@ export default {
                 27,
                 {
                     "upsertPermissionFlagsInput": [
-                        435,
+                        436,
                         "UpsertPermissionFlagsInput!"
                     ]
                 }
@@ -7886,7 +7888,7 @@ export default {
                 26,
                 {
                     "upsertFieldPermissionsInput": [
-                        436,
+                        437,
                         "UpsertFieldPermissionsInput!"
                     ]
                 }
@@ -7895,7 +7897,7 @@ export default {
                 232,
                 {
                     "input": [
-                        438,
+                        439,
                         "UpsertRowLevelPermissionPredicatesInput!"
                     ]
                 }
@@ -7923,34 +7925,34 @@ export default {
                 }
             ],
             "runAgent": [
-                294,
+                295,
                 {
                     "input": [
-                        441,
+                        442,
                         "RunAgentInput!"
                     ]
                 }
             ],
             "createWebhook": [
-                291,
+                292,
                 {
                     "input": [
-                        442,
+                        443,
                         "CreateWebhookInput!"
                     ]
                 }
             ],
             "updateWebhook": [
-                291,
+                292,
                 {
                     "input": [
-                        443,
+                        444,
                         "UpdateWebhookInput!"
                     ]
                 }
             ],
             "deleteWebhook": [
-                291,
+                292,
                 {
                     "id": [
                         3,
@@ -7962,7 +7964,7 @@ export default {
                 44,
                 {
                     "input": [
-                        445,
+                        446,
                         "CreateOneFieldMetadataInput!"
                     ]
                 }
@@ -7971,7 +7973,7 @@ export default {
                 44,
                 {
                     "input": [
-                        447,
+                        448,
                         "UpdateOneFieldMetadataInput!"
                     ]
                 }
@@ -7980,7 +7982,7 @@ export default {
                 44,
                 {
                     "input": [
-                        449,
+                        450,
                         "DeleteOneFieldInput!"
                     ]
                 }
@@ -7989,7 +7991,7 @@ export default {
                 66,
                 {
                     "input": [
-                        450,
+                        451,
                         "CreateViewGroupInput!"
                     ]
                 }
@@ -7998,7 +8000,7 @@ export default {
                 66,
                 {
                     "inputs": [
-                        450,
+                        451,
                         "[CreateViewGroupInput!]!"
                     ]
                 }
@@ -8007,7 +8009,7 @@ export default {
                 66,
                 {
                     "input": [
-                        451,
+                        452,
                         "UpdateViewGroupInput!"
                     ]
                 }
@@ -8016,7 +8018,7 @@ export default {
                 66,
                 {
                     "inputs": [
-                        451,
+                        452,
                         "[UpdateViewGroupInput!]!"
                     ]
                 }
@@ -8025,7 +8027,7 @@ export default {
                 66,
                 {
                     "input": [
-                        453,
+                        454,
                         "DeleteViewGroupInput!"
                     ]
                 }
@@ -8034,43 +8036,43 @@ export default {
                 66,
                 {
                     "input": [
-                        454,
+                        455,
                         "DestroyViewGroupInput!"
                     ]
                 }
             ],
             "updateMessageFolder": [
-                325,
+                326,
                 {
                     "input": [
-                        455,
+                        456,
                         "UpdateMessageFolderInput!"
                     ]
                 }
             ],
             "updateMessageFolders": [
-                325,
+                326,
                 {
                     "input": [
-                        457,
+                        458,
                         "UpdateMessageFoldersInput!"
                     ]
                 }
             ],
             "updateCalendarChannel": [
-                320,
+                321,
                 {
                     "input": [
-                        458,
+                        459,
                         "UpdateCalendarChannelInput!"
                     ]
                 }
             ],
             "createChatThread": [
-                311
+                312
             ],
             "sendChatMessage": [
-                315,
+                316,
                 {
                     "threadId": [
                         3,
@@ -8091,7 +8093,7 @@ export default {
                         1
                     ],
                     "fileAttachments": [
-                        460,
+                        461,
                         "[FileAttachmentInput!]"
                     ]
                 }
@@ -8106,7 +8108,7 @@ export default {
                 }
             ],
             "renameChatThread": [
-                311,
+                312,
                 {
                     "id": [
                         3,
@@ -8119,7 +8121,7 @@ export default {
                 }
             ],
             "archiveChatThread": [
-                311,
+                312,
                 {
                     "id": [
                         3,
@@ -8128,7 +8130,7 @@ export default {
                 }
             ],
             "unarchiveChatThread": [
-                311,
+                312,
                 {
                     "id": [
                         3,
@@ -8155,25 +8157,25 @@ export default {
                 }
             ],
             "createSkill": [
-                309,
+                310,
                 {
                     "input": [
-                        461,
+                        462,
                         "CreateSkillInput!"
                     ]
                 }
             ],
             "updateSkill": [
-                309,
+                310,
                 {
                     "input": [
-                        462,
+                        463,
                         "UpdateSkillInput!"
                     ]
                 }
             ],
             "deleteSkill": [
-                309,
+                310,
                 {
                     "id": [
                         3,
@@ -8182,7 +8184,7 @@ export default {
                 }
             ],
             "activateSkill": [
-                309,
+                310,
                 {
                     "id": [
                         3,
@@ -8191,7 +8193,7 @@ export default {
                 }
             ],
             "deactivateSkill": [
-                309,
+                310,
                 {
                     "id": [
                         3,
@@ -8200,7 +8202,7 @@ export default {
                 }
             ],
             "evaluateAgentTurn": [
-                317,
+                318,
                 {
                     "turnId": [
                         3,
@@ -8209,7 +8211,7 @@ export default {
                 }
             ],
             "runEvaluationInput": [
-                318,
+                319,
                 {
                     "agentId": [
                         3,
@@ -8222,16 +8224,16 @@ export default {
                 }
             ],
             "getAuthorizationUrlForSSO": [
-                244,
+                245,
                 {
                     "input": [
-                        463,
+                        464,
                         "GetAuthorizationUrlForSSOInput!"
                     ]
                 }
             ],
             "getLoginTokenFromCredentials": [
-                253,
+                254,
                 {
                     "email": [
                         1,
@@ -8257,7 +8259,7 @@ export default {
                 }
             ],
             "signIn": [
-                242,
+                243,
                 {
                     "email": [
                         1,
@@ -8279,7 +8281,7 @@ export default {
                 }
             ],
             "verifyEmailAndGetLoginToken": [
-                250,
+                251,
                 {
                     "emailVerificationToken": [
                         1,
@@ -8299,7 +8301,7 @@ export default {
                 }
             ],
             "verifyEmailAndGetWorkspaceAgnosticToken": [
-                242,
+                243,
                 {
                     "emailVerificationToken": [
                         1,
@@ -8315,7 +8317,7 @@ export default {
                 }
             ],
             "getAuthTokensFromOTP": [
-                252,
+                253,
                 {
                     "otp": [
                         1,
@@ -8335,7 +8337,7 @@ export default {
                 }
             ],
             "signUp": [
-                242,
+                243,
                 {
                     "email": [
                         1,
@@ -8357,7 +8359,7 @@ export default {
                 }
             ],
             "signUpInWorkspace": [
-                247,
+                248,
                 {
                     "email": [
                         1,
@@ -8388,13 +8390,13 @@ export default {
                 }
             ],
             "signUpInNewWorkspace": [
-                247
-            ],
-            "generateTransientToken": [
                 248
             ],
+            "generateTransientToken": [
+                249
+            ],
             "getAuthTokensFromLoginToken": [
-                252,
+                253,
                 {
                     "loginToken": [
                         1,
@@ -8407,7 +8409,7 @@ export default {
                 }
             ],
             "authorizeApp": [
-                240,
+                241,
                 {
                     "clientId": [
                         1,
@@ -8429,7 +8431,7 @@ export default {
                 }
             ],
             "renewToken": [
-                252,
+                253,
                 {
                     "appToken": [
                         1,
@@ -8438,7 +8440,7 @@ export default {
                 }
             ],
             "generateApiKeyToken": [
-                251,
+                252,
                 {
                     "apiKeyId": [
                         3,
@@ -8454,7 +8456,7 @@ export default {
                 32
             ],
             "emailPasswordResetLink": [
-                243,
+                244,
                 {
                     "email": [
                         1,
@@ -8466,7 +8468,7 @@ export default {
                 }
             ],
             "updatePasswordViaResetToken": [
-                245,
+                246,
                 {
                     "passwordResetToken": [
                         1,
@@ -8482,7 +8484,7 @@ export default {
                 198,
                 {
                     "input": [
-                        464,
+                        465,
                         "CreateApplicationRegistrationInput!"
                     ]
                 }
@@ -8491,7 +8493,7 @@ export default {
                 7,
                 {
                     "input": [
-                        465,
+                        466,
                         "UpdateApplicationRegistrationInput!"
                     ]
                 }
@@ -8518,7 +8520,7 @@ export default {
                 5,
                 {
                     "input": [
-                        467,
+                        468,
                         "CreateApplicationRegistrationVariableInput!"
                     ]
                 }
@@ -8527,7 +8529,7 @@ export default {
                 5,
                 {
                     "input": [
-                        468,
+                        469,
                         "UpdateApplicationRegistrationVariableInput!"
                     ]
                 }
@@ -8545,7 +8547,7 @@ export default {
                 7,
                 {
                     "file": [
-                        353,
+                        354,
                         "Upload!"
                     ],
                     "universalIdentifier": [
@@ -8567,7 +8569,7 @@ export default {
                 }
             ],
             "initiateOTPProvisioning": [
-                238,
+                239,
                 {
                     "loginToken": [
                         1,
@@ -8580,10 +8582,10 @@ export default {
                 }
             ],
             "initiateOTPProvisioningForAuthenticatedUser": [
-                238
+                239
             ],
             "deleteTwoFactorAuthenticationMethod": [
-                237,
+                238,
                 {
                     "twoFactorAuthenticationMethodId": [
                         3,
@@ -8592,7 +8594,7 @@ export default {
                 }
             ],
             "verifyTwoFactorAuthenticationMethodForAuthenticatedUser": [
-                239,
+                240,
                 {
                     "otp": [
                         1,
@@ -8616,7 +8618,7 @@ export default {
                 6,
                 {
                     "input": [
-                        470,
+                        471,
                         "UpdateWorkspaceMemberSettingsInput!"
                     ]
                 }
@@ -8650,7 +8652,7 @@ export default {
                 76,
                 {
                     "data": [
-                        471,
+                        472,
                         "ActivateWorkspaceInput!"
                     ]
                 }
@@ -8659,7 +8661,7 @@ export default {
                 76,
                 {
                     "data": [
-                        472,
+                        473,
                         "UpdateWorkspaceInput!"
                     ]
                 }
@@ -8674,7 +8676,7 @@ export default {
                 6,
                 {
                     "workspaceMigration": [
-                        473,
+                        474,
                         "WorkspaceMigrationInput!"
                     ]
                 }
@@ -8692,7 +8694,7 @@ export default {
                 223,
                 {
                     "input": [
-                        476,
+                        477,
                         "SetupOIDCSsoInput!"
                     ]
                 }
@@ -8701,7 +8703,7 @@ export default {
                 223,
                 {
                     "input": [
-                        477,
+                        478,
                         "SetupSAMLSsoInput!"
                     ]
                 }
@@ -8710,7 +8712,7 @@ export default {
                 219,
                 {
                     "input": [
-                        478,
+                        479,
                         "DeleteSsoInput!"
                     ]
                 }
@@ -8719,13 +8721,13 @@ export default {
                 220,
                 {
                     "input": [
-                        479,
+                        480,
                         "EditSsoInput!"
                     ]
                 }
             ],
             "createObjectEvent": [
-                305,
+                306,
                 {
                     "event": [
                         1,
@@ -8745,10 +8747,10 @@ export default {
                 }
             ],
             "trackAnalytics": [
-                305,
+                306,
                 {
                     "type": [
-                        480,
+                        481,
                         "AnalyticsType!"
                     ],
                     "name": [
@@ -8763,7 +8765,7 @@ export default {
                 }
             ],
             "duplicateDashboard": [
-                303,
+                304,
                 {
                     "id": [
                         3,
@@ -8772,7 +8774,7 @@ export default {
                 }
             ],
             "impersonate": [
-                256,
+                257,
                 {
                     "userId": [
                         3,
@@ -8785,16 +8787,16 @@ export default {
                 }
             ],
             "sendEmail": [
-                304,
+                305,
                 {
                     "input": [
-                        481,
+                        482,
                         "SendEmailInput!"
                     ]
                 }
             ],
             "startChannelSync": [
-                295,
+                296,
                 {
                     "connectedAccountId": [
                         3,
@@ -8803,14 +8805,14 @@ export default {
                 }
             ],
             "saveImapSmtpCaldavAccount": [
-                290,
+                291,
                 {
                     "handle": [
                         1,
                         "String!"
                     ],
                     "connectionParameters": [
-                        483,
+                        484,
                         "EmailAccountConnectionParameters!"
                     ],
                     "id": [
@@ -8822,13 +8824,13 @@ export default {
                 169,
                 {
                     "input": [
-                        485,
+                        486,
                         "UpdateLabPublicFeatureFlagInput!"
                     ]
                 }
             ],
             "createPublicDomain": [
-                265,
+                266,
                 {
                     "domain": [
                         1,
@@ -8840,7 +8842,7 @@ export default {
                 }
             ],
             "updatePublicDomain": [
-                265,
+                266,
                 {
                     "domain": [
                         1,
@@ -8873,7 +8875,7 @@ export default {
                 78,
                 {
                     "input": [
-                        486,
+                        487,
                         "CreateOneAppTokenInput!"
                     ]
                 }
@@ -8906,7 +8908,7 @@ export default {
                 6
             ],
             "createDevelopmentApplication": [
-                260,
+                261,
                 {
                     "universalIdentifier": [
                         1,
@@ -8928,7 +8930,7 @@ export default {
                 }
             ],
             "syncApplication": [
-                261,
+                262,
                 {
                     "manifest": [
                         15,
@@ -8940,10 +8942,10 @@ export default {
                 }
             ],
             "uploadApplicationFile": [
-                262,
+                263,
                 {
                     "file": [
-                        353,
+                        354,
                         "Upload!"
                     ],
                     "applicationUniversalIdentifier": [
@@ -8951,7 +8953,7 @@ export default {
                         "String!"
                     ],
                     "fileFolder": [
-                        488,
+                        489,
                         "FileFolder!"
                     ],
                     "filePath": [
@@ -9060,7 +9062,7 @@ export default {
                 3
             ],
             "update": [
-                352
+                353
             ],
             "__typename": [
                 1
@@ -9170,7 +9172,7 @@ export default {
                 3
             ],
             "update": [
-                358
+                359
             ],
             "__typename": [
                 1
@@ -9329,17 +9331,17 @@ export default {
                 3
             ],
             "viewFields": [
-                364
-            ],
-            "viewFilters": [
                 365
             ],
-            "viewFilterGroups": [
+            "viewFilters": [
                 366
             ],
-            "viewSorts": [
+            "viewFilterGroups": [
                 367
             ],
+            "viewSorts": [
+                368
+            ],
             "__typename": [
                 1
             ]
@@ -9449,7 +9451,7 @@ export default {
                 3
             ],
             "update": [
-                370
+                371
             ],
             "__typename": [
                 1
@@ -9487,7 +9489,7 @@ export default {
                 3
             ],
             "update": [
-                374
+                375
             ],
             "__typename": [
                 1
@@ -9563,7 +9565,7 @@ export default {
                 3
             ],
             "update": [
-                379
+                380
             ],
             "__typename": [
                 1
@@ -9627,10 +9629,10 @@ export default {
                 3
             ],
             "groups": [
-                384
+                385
             ],
             "fields": [
-                385
+                386
             ],
             "__typename": [
                 1
@@ -9650,7 +9652,7 @@ export default {
                 6
             ],
             "fields": [
-                385
+                386
             ],
             "__typename": [
                 1
@@ -9818,7 +9820,7 @@ export default {
                 3
             ],
             "tabs": [
-                397
+                398
             ],
             "__typename": [
                 1
@@ -9841,7 +9843,7 @@ export default {
                 89
             ],
             "widgets": [
-                398
+                399
             ],
             "__typename": [
                 1
@@ -9864,7 +9866,7 @@ export default {
                 3
             ],
             "gridPosition": [
-                399
+                400
             ],
             "position": [
                 15
@@ -9913,7 +9915,7 @@ export default {
                 3
             ],
             "gridPosition": [
-                399
+                400
             ],
             "position": [
                 15
@@ -9939,7 +9941,7 @@ export default {
                 3
             ],
             "gridPosition": [
-                399
+                400
             ],
             "position": [
                 15
@@ -10011,7 +10013,7 @@ export default {
                 3
             ],
             "update": [
-                405
+                406
             ],
             "__typename": [
                 1
@@ -10171,7 +10173,7 @@ export default {
                 3
             ],
             "update": [
-                410
+                411
             ],
             "__typename": [
                 1
@@ -10190,7 +10192,7 @@ export default {
         },
         "CreateOneObjectInput": {
             "object": [
-                412
+                413
             ],
             "__typename": [
                 1
@@ -10250,7 +10252,7 @@ export default {
         },
         "UpdateOneObjectInput": {
             "update": [
-                415
+                416
             ],
             "id": [
                 3
@@ -10305,7 +10307,7 @@ export default {
         },
         "CreateOneIndexInput": {
             "index": [
-                417
+                418
             ],
             "__typename": [
                 1
@@ -10316,7 +10318,7 @@ export default {
                 3
             ],
             "fields": [
-                418
+                419
             ],
             "indexType": [
                 48
@@ -10477,7 +10479,7 @@ export default {
                 1
             ],
             "visibility": [
-                283
+                284
             ],
             "__typename": [
                 1
@@ -10494,7 +10496,7 @@ export default {
                 1
             ],
             "visibility": [
-                283
+                284
             ],
             "__typename": [
                 1
@@ -10505,7 +10507,7 @@ export default {
                 3
             ],
             "update": [
-                427
+                428
             ],
             "__typename": [
                 1
@@ -10513,16 +10515,16 @@ export default {
         },
         "UpdateMessageChannelInputUpdates": {
             "visibility": [
-                270
+                271
             ],
             "isContactAutoCreationEnabled": [
                 6
             ],
             "contactAutoCreationPolicy": [
-                272
+                273
             ],
             "messageFolderImportPolicy": [
-                273
+                274
             ],
             "isSyncEnabled": [
                 6
@@ -10599,7 +10601,7 @@ export default {
         },
         "UpdateRoleInput": {
             "update": [
-                432
+                433
             ],
             "id": [
                 3
@@ -10654,7 +10656,7 @@ export default {
                 3
             ],
             "objectPermissions": [
-                434
+                435
             ],
             "__typename": [
                 1
@@ -10696,7 +10698,7 @@ export default {
                 3
             ],
             "fieldPermissions": [
-                437
+                438
             ],
             "__typename": [
                 1
@@ -10727,10 +10729,10 @@ export default {
                 3
             ],
             "predicates": [
-                439
+                440
             ],
             "predicateGroups": [
-                440
+                441
             ],
             "__typename": [
                 1
@@ -10824,7 +10826,7 @@ export default {
                 3
             ],
             "update": [
-                444
+                445
             ],
             "__typename": [
                 1
@@ -10849,7 +10851,7 @@ export default {
         },
         "CreateOneFieldMetadataInput": {
             "field": [
-                446
+                447
             ],
             "__typename": [
                 1
@@ -10925,7 +10927,7 @@ export default {
                 3
             ],
             "update": [
-                448
+                449
             ],
             "__typename": [
                 1
@@ -11020,7 +11022,7 @@ export default {
                 3
             ],
             "update": [
-                452
+                453
             ],
             "__typename": [
                 1
@@ -11064,7 +11066,7 @@ export default {
                 3
             ],
             "update": [
-                456
+                457
             ],
             "__typename": [
                 1
@@ -11083,7 +11085,7 @@ export default {
                 3
             ],
             "update": [
-                456
+                457
             ],
             "__typename": [
                 1
@@ -11094,7 +11096,7 @@ export default {
                 3
             ],
             "update": [
-                459
+                460
             ],
             "__typename": [
                 1
@@ -11102,13 +11104,13 @@ export default {
         },
         "UpdateCalendarChannelInputUpdates": {
             "visibility": [
-                323
+                324
             ],
             "isContactAutoCreationEnabled": [
                 6
             ],
             "contactAutoCreationPolicy": [
-                324
+                325
             ],
             "isSyncEnabled": [
                 6
@@ -11210,7 +11212,7 @@ export default {
                 1
             ],
             "update": [
-                466
+                467
             ],
             "__typename": [
                 1
@@ -11258,7 +11260,7 @@ export default {
                 1
             ],
             "update": [
-                469
+                470
             ],
             "__typename": [
                 1
@@ -11376,7 +11378,7 @@ export default {
         },
         "WorkspaceMigrationInput": {
             "actions": [
-                474
+                475
             ],
             "__typename": [
                 1
@@ -11384,10 +11386,10 @@ export default {
         },
         "WorkspaceMigrationDeleteActionInput": {
             "type": [
-                475
+                476
             ],
             "metadataName": [
-                328
+                329
             ],
             "universalIdentifier": [
                 1
@@ -11480,7 +11482,7 @@ export default {
                 1
             ],
             "files": [
-                482
+                483
             ],
             "__typename": [
                 1
@@ -11499,13 +11501,13 @@ export default {
         },
         "EmailAccountConnectionParameters": {
             "IMAP": [
-                484
+                485
             ],
             "SMTP": [
-                484
+                485
             ],
             "CALDAV": [
-                484
+                485
             ],
             "__typename": [
                 1
@@ -11524,8 +11526,8 @@ export default {
             "password": [
                 1
             ],
-            "secure": [
-                6
+            "connectionSecurity": [
+                235
             ],
             "__typename": [
                 1
@@ -11544,7 +11546,7 @@ export default {
         },
         "CreateOneAppTokenInput": {
             "appToken": [
-                487
+                488
             ],
             "__typename": [
                 1
@@ -11573,13 +11575,13 @@ export default {
                 233,
                 {
                     "input": [
-                        490,
+                        491,
                         "LogicFunctionLogsInput!"
                     ]
                 }
             ],
             "onAgentChatEvent": [
-                316,
+                317,
                 {
                     "threadId": [
                         3,
@@ -11588,10 +11590,10 @@ export default {
                 }
             ],
             "eventLogsLive": [
-                306,
+                307,
                 {
                     "table": [
-                        339,
+                        340,
                         "EventLogTable!"
                     ]
                 }
diff --git a/packages/twenty-front/src/generated-metadata/graphql.ts b/packages/twenty-front/src/generated-metadata/graphql.ts
index 999fa66196..2e329d8f5b 100644
--- a/packages/twenty-front/src/generated-metadata/graphql.ts
+++ b/packages/twenty-front/src/generated-metadata/graphql.ts
@@ -986,10 +986,10 @@ export type ConnectedImapSmtpCaldavAccount = {
 };
 
 export type ConnectionParametersInput = {
+  connectionSecurity?: InputMaybe<EmailConnectionSecurity>;
   host: Scalars['String']['input'];
   password?: InputMaybe<Scalars['String']['input']>;
   port: Scalars['Float']['input'];
-  secure?: InputMaybe<Scalars['Boolean']['input']>;
   username?: InputMaybe<Scalars['String']['input']>;
 };
 
@@ -1487,6 +1487,12 @@ export type EmailAccountConnectionParameters = {
   SMTP?: InputMaybe<ConnectionParametersInput>;
 };
 
+export enum EmailConnectionSecurity {
+  NONE = 'NONE',
+  SSL_TLS = 'SSL_TLS',
+  STARTTLS = 'STARTTLS'
+}
+
 export type EmailPasswordResetLink = {
   __typename?: 'EmailPasswordResetLink';
   /** Boolean that confirms query was dispatched */
@@ -1987,9 +1993,9 @@ export type ImapSmtpCaldavPublicConnectionParameters = {
 
 export type ImapSmtpCaldavPublicConnectionParams = {
   __typename?: 'ImapSmtpCaldavPublicConnectionParams';
+  connectionSecurity?: Maybe<EmailConnectionSecurity>;
   host: Scalars['String']['output'];
   port: Scalars['Float']['output'];
-  secure?: Maybe<Scalars['Boolean']['output']>;
   username?: Maybe<Scalars['String']['output']>;
 };
 
@@ -4166,9 +4172,9 @@ export type PublicApplicationRegistration = {
 
 export type PublicConnectionParametersOutput = {
   __typename?: 'PublicConnectionParametersOutput';
+  connectionSecurity?: Maybe<EmailConnectionSecurity>;
   host: Scalars['String']['output'];
   port: Scalars['Float']['output'];
-  secure?: Maybe<Scalars['Boolean']['output']>;
   username?: Maybe<Scalars['String']['output']>;
 };
 
@@ -7482,7 +7488,7 @@ export type GetConnectedImapSmtpCaldavAccountQueryVariables = Exact<{
 }>;
 
 
-export type GetConnectedImapSmtpCaldavAccountQuery = { __typename?: 'Query', getConnectedImapSmtpCaldavAccount: { __typename?: 'ConnectedImapSmtpCaldavAccount', id: string, handle: string, provider: string, userWorkspaceId: string, connectionParameters?: { __typename?: 'ImapSmtpCaldavPublicConnectionParameters', IMAP?: { __typename?: 'ImapSmtpCaldavPublicConnectionParams', host: string, port: number, secure?: boolean | null, username?: string | null } | null, SMTP?: { __typename?: 'ImapSmtpCaldavPublicConnectionParams', host: string, username?: string | null, port: number, secure?: boolean | null } | null, CALDAV?: { __typename?: 'ImapSmtpCaldavPublicConnectionParams', host: string, port: number, secure?: boolean | null, username?: string | null } | null } | null } };
+export type GetConnectedImapSmtpCaldavAccountQuery = { __typename?: 'Query', getConnectedImapSmtpCaldavAccount: { __typename?: 'ConnectedImapSmtpCaldavAccount', id: string, handle: string, provider: string, userWorkspaceId: string, connectionParameters?: { __typename?: 'ImapSmtpCaldavPublicConnectionParameters', IMAP?: { __typename?: 'ImapSmtpCaldavPublicConnectionParams', host: string, port: number, connectionSecurity?: EmailConnectionSecurity | null, username?: string | null } | null, SMTP?: { __typename?: 'ImapSmtpCaldavPublicConnectionParams', host: string, username?: string | null, port: number, connectionSecurity?: EmailConnectionSecurity | null } | null, CALDAV?: { __typename?: 'ImapSmtpCaldavPublicConnectionParams', host: string, port: number, connectionSecurity?: EmailConnectionSecurity | null, username?: string | null } | null } | null } };
 
 export type MyCalendarChannelsQueryVariables = Exact<{
   connectedAccountId?: InputMaybe<Scalars['UUID']['input']>;
@@ -7494,7 +7500,7 @@ export type MyCalendarChannelsQuery = { __typename?: 'Query', myCalendarChannels
 export type MyConnectedAccountsQueryVariables = Exact<{ [key: string]: never; }>;
 
 
-export type MyConnectedAccountsQuery = { __typename?: 'Query', myConnectedAccounts: Array<{ __typename?: 'ConnectedAccountPublicDTO', id: string, handle: string, provider: string, authFailedAt?: string | null, archivedAt?: string | null, scopes?: Array<string> | null, handleAliases?: Array<string> | null, lastSignedInAt?: string | null, userWorkspaceId: string, connectionProviderId?: string | null, name?: string | null, visibility: string, lastCredentialsRefreshedAt?: string | null, createdAt: string, updatedAt: string, connectionParameters?: { __typename?: 'PublicImapSmtpCaldavConnectionParameters', IMAP?: { __typename?: 'PublicConnectionParametersOutput', host: string, port: number, secure?: boolean | null, username?: string | null } | null, SMTP?: { __typename?: 'PublicConnectionParametersOutput', host: string, port: number, secure?: boolean | null, username?: string | null } | null, CALDAV?: { __typename?: 'PublicConnectionParametersOutput', host: string, username?: string | null } | null } | null }> };
+export type MyConnectedAccountsQuery = { __typename?: 'Query', myConnectedAccounts: Array<{ __typename?: 'ConnectedAccountPublicDTO', id: string, handle: string, provider: string, authFailedAt?: string | null, archivedAt?: string | null, scopes?: Array<string> | null, handleAliases?: Array<string> | null, lastSignedInAt?: string | null, userWorkspaceId: string, connectionProviderId?: string | null, name?: string | null, visibility: string, lastCredentialsRefreshedAt?: string | null, createdAt: string, updatedAt: string, connectionParameters?: { __typename?: 'PublicImapSmtpCaldavConnectionParameters', IMAP?: { __typename?: 'PublicConnectionParametersOutput', host: string, port: number, connectionSecurity?: EmailConnectionSecurity | null, username?: string | null } | null, SMTP?: { __typename?: 'PublicConnectionParametersOutput', host: string, port: number, connectionSecurity?: EmailConnectionSecurity | null, username?: string | null } | null, CALDAV?: { __typename?: 'PublicConnectionParametersOutput', host: string, username?: string | null } | null } | null }> };
 
 export type MyMessageChannelsQueryVariables = Exact<{
   connectedAccountId?: InputMaybe<Scalars['UUID']['input']>;
@@ -8706,9 +8712,9 @@ export const UpdateCalendarChannelDocument = {"kind":"Document","definitions":[{
 export const UpdateMessageChannelDocument = {"kind":"Document","definitions":[{"kind":"OperationDefinition","operation":"mutation","name":{"kind":"Name","value":"UpdateMessageChannel"},"variableDefinitions":[{"kind":"VariableDefinition","variable":{"kind":"Variable","name":{"kind":"Name","value":"input"}},"type":{"kind":"NonNullType","type":{"kind":"NamedType","name":{"kind":"Name","value":"UpdateMessageChannelInput"}}}}],"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"updateMessageChannel"},"arguments":[{"kind":"Argument","name":{"kind":"Name","value":"input"},"value":{"kind":"Variable","name":{"kind":"Name","value":"input"}}}],"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"id"}},{"kind":"Field","name":{"kind":"Name","value":"visibility"}},{"kind":"Field","name":{"kind":"Name","value":"contactAutoCreationPolicy"}},{"kind":"Field","name":{"kind":"Name","value":"excludeNonProfessionalEmails"}},{"kind":"Field","name":{"kind":"Name","value":"excludeGroupEmails"}},{"kind":"Field","name":{"kind":"Name","value":"messageFolderImportPolicy"}}]}}]}}]} as unknown as DocumentNode<UpdateMessageChannelMutation, UpdateMessageChannelMutationVariables>;
 export const UpdateMessageFolderDocument = {"kind":"Document","definitions":[{"kind":"OperationDefinition","operation":"mutation","name":{"kind":"Name","value":"UpdateMessageFolder"},"variableDefinitions":[{"kind":"VariableDefinition","variable":{"kind":"Variable","name":{"kind":"Name","value":"input"}},"type":{"kind":"NonNullType","type":{"kind":"NamedType","name":{"kind":"Name","value":"UpdateMessageFolderInput"}}}}],"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"updateMessageFolder"},"arguments":[{"kind":"Argument","name":{"kind":"Name","value":"input"},"value":{"kind":"Variable","name":{"kind":"Name","value":"input"}}}],"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"id"}},{"kind":"Field","name":{"kind":"Name","value":"isSynced"}}]}}]}}]} as unknown as DocumentNode<UpdateMessageFolderMutation, UpdateMessageFolderMutationVariables>;
 export const UpdateMessageFoldersDocument = {"kind":"Document","definitions":[{"kind":"OperationDefinition","operation":"mutation","name":{"kind":"Name","value":"UpdateMessageFolders"},"variableDefinitions":[{"kind":"VariableDefinition","variable":{"kind":"Variable","name":{"kind":"Name","value":"input"}},"type":{"kind":"NonNullType","type":{"kind":"NamedType","name":{"kind":"Name","value":"UpdateMessageFoldersInput"}}}}],"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"updateMessageFolders"},"arguments":[{"kind":"Argument","name":{"kind":"Name","value":"input"},"value":{"kind":"Variable","name":{"kind":"Name","value":"input"}}}],"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"id"}},{"kind":"Field","name":{"kind":"Name","value":"isSynced"}}]}}]}}]} as unknown as DocumentNode<UpdateMessageFoldersMutation, UpdateMessageFoldersMutationVariables>;
-export const GetConnectedImapSmtpCaldavAccountDocument = {"kind":"Document","definitions":[{"kind":"OperationDefinition","operation":"query","name":{"kind":"Name","value":"GetConnectedImapSmtpCaldavAccount"},"variableDefinitions":[{"kind":"VariableDefinition","variable":{"kind":"Variable","name":{"kind":"Name","value":"id"}},"type":{"kind":"NonNullType","type":{"kind":"NamedType","name":{"kind":"Name","value":"UUID"}}}}],"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"getConnectedImapSmtpCaldavAccount"},"arguments":[{"kind":"Argument","name":{"kind":"Name","value":"id"},"value":{"kind":"Variable","name":{"kind":"Name","value":"id"}}}],"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"id"}},{"kind":"Field","name":{"kind":"Name","value":"handle"}},{"kind":"Field","name":{"kind":"Name","value":"provider"}},{"kind":"Field","name":{"kind":"Name","value":"userWorkspaceId"}},{"kind":"Field","name":{"kind":"Name","value":"connectionParameters"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"IMAP"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"host"}},{"kind":"Field","name":{"kind":"Name","value":"port"}},{"kind":"Field","name":{"kind":"Name","value":"secure"}},{"kind":"Field","name":{"kind":"Name","value":"username"}}]}},{"kind":"Field","name":{"kind":"Name","value":"SMTP"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"host"}},{"kind":"Field","name":{"kind":"Name","value":"username"}},{"kind":"Field","name":{"kind":"Name","value":"port"}},{"kind":"Field","name":{"kind":"Name","value":"secure"}}]}},{"kind":"Field","name":{"kind":"Name","value":"CALDAV"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"host"}},{"kind":"Field","name":{"kind":"Name","value":"port"}},{"kind":"Field","name":{"kind":"Name","value":"secure"}},{"kind":"Field","name":{"kind":"Name","value":"username"}}]}}]}}]}}]}}]} as unknown as DocumentNode<GetConnectedImapSmtpCaldavAccountQuery, GetConnectedImapSmtpCaldavAccountQueryVariables>;
+export const GetConnectedImapSmtpCaldavAccountDocument = {"kind":"Document","definitions":[{"kind":"OperationDefinition","operation":"query","name":{"kind":"Name","value":"GetConnectedImapSmtpCaldavAccount"},"variableDefinitions":[{"kind":"VariableDefinition","variable":{"kind":"Variable","name":{"kind":"Name","value":"id"}},"type":{"kind":"NonNullType","type":{"kind":"NamedType","name":{"kind":"Name","value":"UUID"}}}}],"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"getConnectedImapSmtpCaldavAccount"},"arguments":[{"kind":"Argument","name":{"kind":"Name","value":"id"},"value":{"kind":"Variable","name":{"kind":"Name","value":"id"}}}],"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"id"}},{"kind":"Field","name":{"kind":"Name","value":"handle"}},{"kind":"Field","name":{"kind":"Name","value":"provider"}},{"kind":"Field","name":{"kind":"Name","value":"userWorkspaceId"}},{"kind":"Field","name":{"kind":"Name","value":"connectionParameters"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"IMAP"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"host"}},{"kind":"Field","name":{"kind":"Name","value":"port"}},{"kind":"Field","name":{"kind":"Name","value":"connectionSecurity"}},{"kind":"Field","name":{"kind":"Name","value":"username"}}]}},{"kind":"Field","name":{"kind":"Name","value":"SMTP"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"host"}},{"kind":"Field","name":{"kind":"Name","value":"username"}},{"kind":"Field","name":{"kind":"Name","value":"port"}},{"kind":"Field","name":{"kind":"Name","value":"connectionSecurity"}}]}},{"kind":"Field","name":{"kind":"Name","value":"CALDAV"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"host"}},{"kind":"Field","name":{"kind":"Name","value":"port"}},{"kind":"Field","name":{"kind":"Name","value":"connectionSecurity"}},{"kind":"Field","name":{"kind":"Name","value":"username"}}]}}]}}]}}]}}]} as unknown as DocumentNode<GetConnectedImapSmtpCaldavAccountQuery, GetConnectedImapSmtpCaldavAccountQueryVariables>;
 export const MyCalendarChannelsDocument = {"kind":"Document","definitions":[{"kind":"OperationDefinition","operation":"query","name":{"kind":"Name","value":"MyCalendarChannels"},"variableDefinitions":[{"kind":"VariableDefinition","variable":{"kind":"Variable","name":{"kind":"Name","value":"connectedAccountId"}},"type":{"kind":"NamedType","name":{"kind":"Name","value":"UUID"}}}],"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"myCalendarChannels"},"arguments":[{"kind":"Argument","name":{"kind":"Name","value":"connectedAccountId"},"value":{"kind":"Variable","name":{"kind":"Name","value":"connectedAccountId"}}}],"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"id"}},{"kind":"Field","name":{"kind":"Name","value":"handle"}},{"kind":"Field","name":{"kind":"Name","value":"visibility"}},{"kind":"Field","name":{"kind":"Name","value":"syncStatus"}},{"kind":"Field","name":{"kind":"Name","value":"syncStage"}},{"kind":"Field","name":{"kind":"Name","value":"syncStageStartedAt"}},{"kind":"Field","name":{"kind":"Name","value":"isContactAutoCreationEnabled"}},{"kind":"Field","name":{"kind":"Name","value":"contactAutoCreationPolicy"}},{"kind":"Field","name":{"kind":"Name","value":"isSyncEnabled"}},{"kind":"Field","name":{"kind":"Name","value":"connectedAccountId"}},{"kind":"Field","name":{"kind":"Name","value":"createdAt"}},{"kind":"Field","name":{"kind":"Name","value":"updatedAt"}}]}}]}}]} as unknown as DocumentNode<MyCalendarChannelsQuery, MyCalendarChannelsQueryVariables>;
-export const MyConnectedAccountsDocument = {"kind":"Document","definitions":[{"kind":"OperationDefinition","operation":"query","name":{"kind":"Name","value":"MyConnectedAccounts"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"myConnectedAccounts"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"id"}},{"kind":"Field","name":{"kind":"Name","value":"handle"}},{"kind":"Field","name":{"kind":"Name","value":"provider"}},{"kind":"Field","name":{"kind":"Name","value":"authFailedAt"}},{"kind":"Field","name":{"kind":"Name","value":"archivedAt"}},{"kind":"Field","name":{"kind":"Name","value":"scopes"}},{"kind":"Field","name":{"kind":"Name","value":"handleAliases"}},{"kind":"Field","name":{"kind":"Name","value":"lastSignedInAt"}},{"kind":"Field","name":{"kind":"Name","value":"userWorkspaceId"}},{"kind":"Field","name":{"kind":"Name","value":"connectionProviderId"}},{"kind":"Field","name":{"kind":"Name","value":"name"}},{"kind":"Field","name":{"kind":"Name","value":"visibility"}},{"kind":"Field","name":{"kind":"Name","value":"lastCredentialsRefreshedAt"}},{"kind":"Field","name":{"kind":"Name","value":"connectionParameters"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"IMAP"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"host"}},{"kind":"Field","name":{"kind":"Name","value":"port"}},{"kind":"Field","name":{"kind":"Name","value":"secure"}},{"kind":"Field","name":{"kind":"Name","value":"username"}}]}},{"kind":"Field","name":{"kind":"Name","value":"SMTP"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"host"}},{"kind":"Field","name":{"kind":"Name","value":"port"}},{"kind":"Field","name":{"kind":"Name","value":"secure"}},{"kind":"Field","name":{"kind":"Name","value":"username"}}]}},{"kind":"Field","name":{"kind":"Name","value":"CALDAV"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"host"}},{"kind":"Field","name":{"kind":"Name","value":"username"}}]}}]}},{"kind":"Field","name":{"kind":"Name","value":"createdAt"}},{"kind":"Field","name":{"kind":"Name","value":"updatedAt"}}]}}]}}]} as unknown as DocumentNode<MyConnectedAccountsQuery, MyConnectedAccountsQueryVariables>;
+export const MyConnectedAccountsDocument = {"kind":"Document","definitions":[{"kind":"OperationDefinition","operation":"query","name":{"kind":"Name","value":"MyConnectedAccounts"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"myConnectedAccounts"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"id"}},{"kind":"Field","name":{"kind":"Name","value":"handle"}},{"kind":"Field","name":{"kind":"Name","value":"provider"}},{"kind":"Field","name":{"kind":"Name","value":"authFailedAt"}},{"kind":"Field","name":{"kind":"Name","value":"archivedAt"}},{"kind":"Field","name":{"kind":"Name","value":"scopes"}},{"kind":"Field","name":{"kind":"Name","value":"handleAliases"}},{"kind":"Field","name":{"kind":"Name","value":"lastSignedInAt"}},{"kind":"Field","name":{"kind":"Name","value":"userWorkspaceId"}},{"kind":"Field","name":{"kind":"Name","value":"connectionProviderId"}},{"kind":"Field","name":{"kind":"Name","value":"name"}},{"kind":"Field","name":{"kind":"Name","value":"visibility"}},{"kind":"Field","name":{"kind":"Name","value":"lastCredentialsRefreshedAt"}},{"kind":"Field","name":{"kind":"Name","value":"connectionParameters"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"IMAP"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"host"}},{"kind":"Field","name":{"kind":"Name","value":"port"}},{"kind":"Field","name":{"kind":"Name","value":"connectionSecurity"}},{"kind":"Field","name":{"kind":"Name","value":"username"}}]}},{"kind":"Field","name":{"kind":"Name","value":"SMTP"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"host"}},{"kind":"Field","name":{"kind":"Name","value":"port"}},{"kind":"Field","name":{"kind":"Name","value":"connectionSecurity"}},{"kind":"Field","name":{"kind":"Name","value":"username"}}]}},{"kind":"Field","name":{"kind":"Name","value":"CALDAV"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"host"}},{"kind":"Field","name":{"kind":"Name","value":"username"}}]}}]}},{"kind":"Field","name":{"kind":"Name","value":"createdAt"}},{"kind":"Field","name":{"kind":"Name","value":"updatedAt"}}]}}]}}]} as unknown as DocumentNode<MyConnectedAccountsQuery, MyConnectedAccountsQueryVariables>;
 export const MyMessageChannelsDocument = {"kind":"Document","definitions":[{"kind":"OperationDefinition","operation":"query","name":{"kind":"Name","value":"MyMessageChannels"},"variableDefinitions":[{"kind":"VariableDefinition","variable":{"kind":"Variable","name":{"kind":"Name","value":"connectedAccountId"}},"type":{"kind":"NamedType","name":{"kind":"Name","value":"UUID"}}}],"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"myMessageChannels"},"arguments":[{"kind":"Argument","name":{"kind":"Name","value":"connectedAccountId"},"value":{"kind":"Variable","name":{"kind":"Name","value":"connectedAccountId"}}}],"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"id"}},{"kind":"Field","name":{"kind":"Name","value":"handle"}},{"kind":"Field","name":{"kind":"Name","value":"visibility"}},{"kind":"Field","name":{"kind":"Name","value":"type"}},{"kind":"Field","name":{"kind":"Name","value":"isContactAutoCreationEnabled"}},{"kind":"Field","name":{"kind":"Name","value":"contactAutoCreationPolicy"}},{"kind":"Field","name":{"kind":"Name","value":"messageFolderImportPolicy"}},{"kind":"Field","name":{"kind":"Name","value":"excludeNonProfessionalEmails"}},{"kind":"Field","name":{"kind":"Name","value":"excludeGroupEmails"}},{"kind":"Field","name":{"kind":"Name","value":"isSyncEnabled"}},{"kind":"Field","name":{"kind":"Name","value":"syncStatus"}},{"kind":"Field","name":{"kind":"Name","value":"syncStage"}},{"kind":"Field","name":{"kind":"Name","value":"syncStageStartedAt"}},{"kind":"Field","name":{"kind":"Name","value":"connectedAccountId"}},{"kind":"Field","name":{"kind":"Name","value":"connectedAccount"},"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"id"}},{"kind":"Field","name":{"kind":"Name","value":"handle"}}]}},{"kind":"Field","name":{"kind":"Name","value":"createdAt"}},{"kind":"Field","name":{"kind":"Name","value":"updatedAt"}}]}}]}}]} as unknown as DocumentNode<MyMessageChannelsQuery, MyMessageChannelsQueryVariables>;
 export const MyMessageFoldersDocument = {"kind":"Document","definitions":[{"kind":"OperationDefinition","operation":"query","name":{"kind":"Name","value":"MyMessageFolders"},"variableDefinitions":[{"kind":"VariableDefinition","variable":{"kind":"Variable","name":{"kind":"Name","value":"messageChannelId"}},"type":{"kind":"NamedType","name":{"kind":"Name","value":"UUID"}}}],"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"myMessageFolders"},"arguments":[{"kind":"Argument","name":{"kind":"Name","value":"messageChannelId"},"value":{"kind":"Variable","name":{"kind":"Name","value":"messageChannelId"}}}],"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"id"}},{"kind":"Field","name":{"kind":"Name","value":"name"}},{"kind":"Field","name":{"kind":"Name","value":"isSynced"}},{"kind":"Field","name":{"kind":"Name","value":"isSentFolder"}},{"kind":"Field","name":{"kind":"Name","value":"parentFolderId"}},{"kind":"Field","name":{"kind":"Name","value":"externalId"}},{"kind":"Field","name":{"kind":"Name","value":"messageChannelId"}},{"kind":"Field","name":{"kind":"Name","value":"createdAt"}},{"kind":"Field","name":{"kind":"Name","value":"updatedAt"}}]}}]}}]} as unknown as DocumentNode<MyMessageFoldersQuery, MyMessageFoldersQueryVariables>;
 export const DeleteApplicationRegistrationDocument = {"kind":"Document","definitions":[{"kind":"OperationDefinition","operation":"mutation","name":{"kind":"Name","value":"DeleteApplicationRegistration"},"variableDefinitions":[{"kind":"VariableDefinition","variable":{"kind":"Variable","name":{"kind":"Name","value":"id"}},"type":{"kind":"NonNullType","type":{"kind":"NamedType","name":{"kind":"Name","value":"String"}}}}],"selectionSet":{"kind":"SelectionSet","selections":[{"kind":"Field","name":{"kind":"Name","value":"deleteApplicationRegistration"},"arguments":[{"kind":"Argument","name":{"kind":"Name","value":"id"},"value":{"kind":"Variable","name":{"kind":"Name","value":"id"}}}]}]}}]} as unknown as DocumentNode<DeleteApplicationRegistrationMutation, DeleteApplicationRegistrationMutationVariables>;
diff --git a/packages/twenty-front/src/modules/settings/accounts/components/SettingsAccountsConnectionForm.tsx b/packages/twenty-front/src/modules/settings/accounts/components/SettingsAccountsConnectionForm.tsx
index d06e726cab..9829ffea98 100644
--- a/packages/twenty-front/src/modules/settings/accounts/components/SettingsAccountsConnectionForm.tsx
+++ b/packages/twenty-front/src/modules/settings/accounts/components/SettingsAccountsConnectionForm.tsx
@@ -192,18 +192,19 @@ export const SettingsAccountsConnectionForm = ({
 
             <StyledFieldGroup>
               <Controller
-                name="IMAP.secure"
+                name="IMAP.connectionSecurity"
                 control={control}
                 render={({ field }) => (
                   <Select
-                    label={t`IMAP Encryption`}
+                    label={t`IMAP Connection security`}
                     options={[
-                      { label: 'SSL/TLS', value: true },
-                      { label: 'None', value: false },
+                      { label: 'None', value: 'NONE' },
+                      { label: 'STARTTLS', value: 'STARTTLS' },
+                      { label: 'SSL/TLS', value: 'SSL_TLS' },
                     ]}
                     value={field.value}
                     onChange={field.onChange}
-                    dropdownId="imap-secure-dropdown"
+                    dropdownId="imap-connection-security-dropdown"
                   />
                 )}
               />
@@ -287,18 +288,19 @@ export const SettingsAccountsConnectionForm = ({
 
             <StyledFieldGroup>
               <Controller
-                name="SMTP.secure"
+                name="SMTP.connectionSecurity"
                 control={control}
                 render={({ field }) => (
                   <Select
-                    label={t`SMTP Encryption`}
+                    label={t`SMTP Connection security`}
                     options={[
-                      { label: 'SSL/TLS', value: true },
-                      { label: 'STARTTLS', value: false },
+                      { label: 'None', value: 'NONE' },
+                      { label: 'STARTTLS', value: 'STARTTLS' },
+                      { label: 'SSL/TLS', value: 'SSL_TLS' },
                     ]}
                     value={field.value}
                     onChange={field.onChange}
-                    dropdownId="smtp-secure-dropdown"
+                    dropdownId="smtp-connection-security-dropdown"
                   />
                 )}
               />
diff --git a/packages/twenty-front/src/modules/settings/accounts/graphql/queries/getConnectedImapSmtpCaldavAccount.ts b/packages/twenty-front/src/modules/settings/accounts/graphql/queries/getConnectedImapSmtpCaldavAccount.ts
index 0042b08b2c..3771cf40cf 100644
--- a/packages/twenty-front/src/modules/settings/accounts/graphql/queries/getConnectedImapSmtpCaldavAccount.ts
+++ b/packages/twenty-front/src/modules/settings/accounts/graphql/queries/getConnectedImapSmtpCaldavAccount.ts
@@ -11,19 +11,19 @@ export const GET_CONNECTED_IMAP_SMTP_CALDAV_ACCOUNT = gql`
         IMAP {
           host
           port
-          secure
+          connectionSecurity
           username
         }
         SMTP {
           host
           username
           port
-          secure
+          connectionSecurity
         }
         CALDAV {
           host
           port
-          secure
+          connectionSecurity
           username
         }
       }
diff --git a/packages/twenty-front/src/modules/settings/accounts/graphql/queries/getMyConnectedAccounts.ts b/packages/twenty-front/src/modules/settings/accounts/graphql/queries/getMyConnectedAccounts.ts
index 8677192bc1..4632c5a889 100644
--- a/packages/twenty-front/src/modules/settings/accounts/graphql/queries/getMyConnectedAccounts.ts
+++ b/packages/twenty-front/src/modules/settings/accounts/graphql/queries/getMyConnectedAccounts.ts
@@ -20,13 +20,13 @@ export const GET_MY_CONNECTED_ACCOUNTS = gql`
         IMAP {
           host
           port
-          secure
+          connectionSecurity
           username
         }
         SMTP {
           host
           port
-          secure
+          connectionSecurity
           username
         }
         CALDAV {
diff --git a/packages/twenty-front/src/modules/settings/accounts/hooks/useImapSmtpCaldavConnectionForm.ts b/packages/twenty-front/src/modules/settings/accounts/hooks/useImapSmtpCaldavConnectionForm.ts
index 11c8e0abaf..29e3a456e0 100644
--- a/packages/twenty-front/src/modules/settings/accounts/hooks/useImapSmtpCaldavConnectionForm.ts
+++ b/packages/twenty-front/src/modules/settings/accounts/hooks/useImapSmtpCaldavConnectionForm.ts
@@ -9,6 +9,7 @@ import { t } from '@lingui/core/macro';
 import { SettingsPath } from 'twenty-shared/types';
 import {
   type ConnectionParametersInput,
+  EmailConnectionSecurity,
   SaveImapSmtpCaldavAccountDocument,
 } from '~/generated-metadata/graphql';
 import { useNavigateSettings } from '~/hooks/useNavigateSettings';
@@ -38,9 +39,25 @@ export type ConnectionFormData = {
 } & ImapSmtpCaldavAccountInput;
 
 const DEFAULT_PROTOCOL_VALUES: Record<string, ConnectionParametersInput> = {
-  IMAP: { host: '', port: 993, password: '', secure: true },
-  SMTP: { host: '', username: '', port: 587, password: '', secure: true },
-  CALDAV: { host: '', port: 443, password: '', secure: true },
+  IMAP: {
+    host: '',
+    port: 993,
+    password: '',
+    connectionSecurity: EmailConnectionSecurity.SSL_TLS,
+  },
+  SMTP: {
+    host: '',
+    username: '',
+    port: 587,
+    password: '',
+    connectionSecurity: EmailConnectionSecurity.STARTTLS,
+  },
+  CALDAV: {
+    host: '',
+    port: 443,
+    password: '',
+    connectionSecurity: EmailConnectionSecurity.SSL_TLS,
+  },
 };
 
 export const useImapSmtpCaldavConnectionForm = ({
diff --git a/packages/twenty-front/src/modules/settings/accounts/validation-schemas/connectionImapSmtpCalDav.ts b/packages/twenty-front/src/modules/settings/accounts/validation-schemas/connectionImapSmtpCalDav.ts
index d2ba749d87..8e5667c943 100644
--- a/packages/twenty-front/src/modules/settings/accounts/validation-schemas/connectionImapSmtpCalDav.ts
+++ b/packages/twenty-front/src/modules/settings/accounts/validation-schemas/connectionImapSmtpCalDav.ts
@@ -13,7 +13,9 @@ const connectionParameters = z
     port: z.int().nullable().default(null),
     username: z.string().optional(),
     password: z.string().default(''),
-    secure: z.boolean().default(true),
+    connectionSecurity: z
+      .enum(['NONE', 'STARTTLS', 'SSL_TLS'])
+      .default('SSL_TLS'),
   })
   .refine(
     (data) => {
diff --git a/packages/twenty-server/src/database/commands/upgrade-version-command/2-15/2-15-instance-command-slow-1781461753981-backfill-connection-security.ts b/packages/twenty-server/src/database/commands/upgrade-version-command/2-15/2-15-instance-command-slow-1781461753981-backfill-connection-security.ts
new file mode 100644
index 0000000000..97fae6c4e4
--- /dev/null
+++ b/packages/twenty-server/src/database/commands/upgrade-version-command/2-15/2-15-instance-command-slow-1781461753981-backfill-connection-security.ts
@@ -0,0 +1,65 @@
+import { DataSource, QueryRunner } from 'typeorm';
+
+import { RegisteredInstanceCommand } from 'src/engine/core-modules/upgrade/decorators/registered-instance-command.decorator';
+import { SlowInstanceCommand } from 'src/engine/core-modules/upgrade/interfaces/slow-instance-command.interface';
+
+// Replaces the legacy `secure` boolean with the `connectionSecurity` enum,
+// preserving the previously deployed on-wire behavior exactly. SMTP used
+// implicit TLS on port 465 (-> SSL_TLS) and opportunistic STARTTLS elsewhere
+// (-> STARTTLS); IMAP used implicit TLS when secure (-> SSL_TLS) and
+// opportunistic STARTTLS otherwise (-> STARTTLS); CalDAV is TLS over its https
+// host (-> SSL_TLS). STARTTLS stays opportunistic so no account is forced onto
+// a stricter handshake than it already used.
+@RegisteredInstanceCommand('2.15.0', 1781461753981, { type: 'slow' })
+export class BackfillConnectionSecuritySlowInstanceCommand
+  implements SlowInstanceCommand
+{
+  async runDataMigration(dataSource: DataSource): Promise<void> {
+    await dataSource.query(
+      `UPDATE "core"."connectedAccount"
+       SET "connectionParameters" = jsonb_set(
+         "connectionParameters" #- '{SMTP,secure}',
+         '{SMTP,connectionSecurity}',
+         to_jsonb(
+           CASE WHEN "connectionParameters"->'SMTP'->>'port' = '465'
+                THEN 'SSL_TLS' ELSE 'STARTTLS' END
+         )
+       )
+       WHERE "connectionParameters" ? 'SMTP'
+         AND NOT "connectionParameters"->'SMTP' ? 'connectionSecurity'`,
+    );
+
+    await dataSource.query(
+      `UPDATE "core"."connectedAccount"
+       SET "connectionParameters" = jsonb_set(
+         "connectionParameters" #- '{IMAP,secure}',
+         '{IMAP,connectionSecurity}',
+         to_jsonb(
+           CASE WHEN "connectionParameters"->'IMAP'->>'secure' = 'false'
+                THEN 'STARTTLS' ELSE 'SSL_TLS' END
+         )
+       )
+       WHERE "connectionParameters" ? 'IMAP'
+         AND NOT "connectionParameters"->'IMAP' ? 'connectionSecurity'`,
+    );
+
+    await dataSource.query(
+      `UPDATE "core"."connectedAccount"
+       SET "connectionParameters" = jsonb_set(
+         "connectionParameters" #- '{CALDAV,secure}',
+         '{CALDAV,connectionSecurity}',
+         to_jsonb('SSL_TLS'::text)
+       )
+       WHERE "connectionParameters" ? 'CALDAV'
+         AND NOT "connectionParameters"->'CALDAV' ? 'connectionSecurity'`,
+    );
+  }
+
+  public async up(_queryRunner: QueryRunner): Promise<void> {
+    return;
+  }
+
+  public async down(_queryRunner: QueryRunner): Promise<void> {
+    return;
+  }
+}
diff --git a/packages/twenty-server/src/database/commands/upgrade-version-command/instance-commands.constant.ts b/packages/twenty-server/src/database/commands/upgrade-version-command/instance-commands.constant.ts
index 19ea4e264e..6a8999d359 100644
--- a/packages/twenty-server/src/database/commands/upgrade-version-command/instance-commands.constant.ts
+++ b/packages/twenty-server/src/database/commands/upgrade-version-command/instance-commands.constant.ts
@@ -70,6 +70,7 @@ import { RenameIsUiReadOnlyToIsUiEditableFastInstanceCommand } from 'src/databas
 import { BackfillNonUiCreatableStandardSystemObjectsSlowInstanceCommand } from 'src/database/commands/upgrade-version-command/2-13/2-13-instance-command-slow-1781277480000-backfill-non-ui-creatable-standard-system-objects';
 import { CommandMenuItemOverridableEntityFastInstanceCommand } from 'src/database/commands/upgrade-version-command/2-13/2-13-instance-command-fast-1781253016028-command-menu-item-overridable-entity';
 import { SetTableWidgetViewsVisibilityToWorkspaceSlowInstanceCommand } from 'src/database/commands/upgrade-version-command/2-14/2-14-instance-command-slow-1781515653781-set-table-widget-views-visibility-to-workspace';
+import { BackfillConnectionSecuritySlowInstanceCommand } from 'src/database/commands/upgrade-version-command/2-15/2-15-instance-command-slow-1781461753981-backfill-connection-security';
 
 export const INSTANCE_COMMANDS = [
   AddViewFieldGroupIdIndexOnViewFieldFastInstanceCommand,
@@ -142,4 +143,5 @@ export const INSTANCE_COMMANDS = [
   BackfillNonUiCreatableStandardSystemObjectsSlowInstanceCommand,
   CommandMenuItemOverridableEntityFastInstanceCommand,
   SetTableWidgetViewsVisibilityToWorkspaceSlowInstanceCommand,
+  BackfillConnectionSecuritySlowInstanceCommand,
 ];
diff --git a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/dtos/imap-smtp-caldav-connected-account.dto.ts b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/dtos/imap-smtp-caldav-connected-account.dto.ts
index a29742a578..7bd7ed6b8a 100644
--- a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/dtos/imap-smtp-caldav-connected-account.dto.ts
+++ b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/dtos/imap-smtp-caldav-connected-account.dto.ts
@@ -2,6 +2,8 @@ import { Field, ObjectType } from '@nestjs/graphql';
 
 import { ConnectedAccountProvider } from 'twenty-shared/types';
 
+import { EmailConnectionSecurity } from 'src/engine/core-modules/imap-smtp-caldav-connection/enums/email-connection-security.enum';
+
 import { UUIDScalarType } from 'src/engine/api/graphql/workspace-schema-builder/graphql-types/scalars';
 
 @ObjectType('ImapSmtpCaldavPublicConnectionParams')
@@ -15,8 +17,8 @@ class PublicConnectionParamsDTO {
   @Field(() => String, { nullable: true })
   username?: string;
 
-  @Field(() => Boolean, { nullable: true })
-  secure?: boolean;
+  @Field(() => EmailConnectionSecurity, { nullable: true })
+  connectionSecurity?: EmailConnectionSecurity;
 }
 
 @ObjectType('ImapSmtpCaldavPublicConnectionParameters')
diff --git a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/dtos/imap-smtp-caldav-connection.input.ts b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/dtos/imap-smtp-caldav-connection.input.ts
index 2b6d1ec723..a7ebc7e351 100644
--- a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/dtos/imap-smtp-caldav-connection.input.ts
+++ b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/dtos/imap-smtp-caldav-connection.input.ts
@@ -1,4 +1,10 @@
-import { Field, InputType } from '@nestjs/graphql';
+import { Field, InputType, registerEnumType } from '@nestjs/graphql';
+
+import { EmailConnectionSecurity } from 'src/engine/core-modules/imap-smtp-caldav-connection/enums/email-connection-security.enum';
+
+registerEnumType(EmailConnectionSecurity, {
+  name: 'EmailConnectionSecurity',
+});
 
 @InputType()
 export class AccountType {
@@ -20,8 +26,8 @@ export class ConnectionParametersInput {
   @Field(() => String, { nullable: true })
   password?: string;
 
-  @Field(() => Boolean, { nullable: true })
-  secure?: boolean;
+  @Field(() => EmailConnectionSecurity, { nullable: true })
+  connectionSecurity?: EmailConnectionSecurity;
 }
 
 @InputType('EmailAccountConnectionParameters')
diff --git a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/enums/email-connection-security.enum.ts b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/enums/email-connection-security.enum.ts
new file mode 100644
index 0000000000..31aeda3b4d
--- /dev/null
+++ b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/enums/email-connection-security.enum.ts
@@ -0,0 +1,5 @@
+export enum EmailConnectionSecurity {
+  NONE = 'NONE',
+  STARTTLS = 'STARTTLS',
+  SSL_TLS = 'SSL_TLS',
+}
diff --git a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/schemas/connection-parameters.schema.ts b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/schemas/connection-parameters.schema.ts
index f979e7ed6e..0bee7e33ee 100644
--- a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/schemas/connection-parameters.schema.ts
+++ b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/schemas/connection-parameters.schema.ts
@@ -1,3 +1,4 @@
+import { EmailConnectionSecurity } from 'src/engine/core-modules/imap-smtp-caldav-connection/enums/email-connection-security.enum';
 import { plaintextStringSchema } from 'src/engine/core-modules/secret-encryption/branded-strings/plaintext-string.type';
 import { z } from 'zod';
 
@@ -6,5 +7,7 @@ export const connectionParametersSchema = z.object({
   port: z.int().positive('Port must be a positive number'),
   username: z.string().optional(),
   password: plaintextStringSchema.min(1, 'Password is required'),
-  secure: z.boolean().optional(),
+  connectionSecurity: z
+    .nativeEnum(EmailConnectionSecurity)
+    .default(EmailConnectionSecurity.SSL_TLS),
 });
diff --git a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/services/__tests__/imap-smtp-caldav-connection.service.spec.ts b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/services/__tests__/imap-smtp-caldav-connection.service.spec.ts
index cd3e20d1eb..25cf60ccad 100644
--- a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/services/__tests__/imap-smtp-caldav-connection.service.spec.ts
+++ b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/services/__tests__/imap-smtp-caldav-connection.service.spec.ts
@@ -1,7 +1,9 @@
 import { Test, type TestingModule } from '@nestjs/testing';
 
+import { createTransport } from 'nodemailer';
 import { type DAVClient } from 'tsdav';
 
+import { EmailConnectionSecurity } from 'src/engine/core-modules/imap-smtp-caldav-connection/enums/email-connection-security.enum';
 import { ImapSmtpCaldavValidatorService } from 'src/engine/core-modules/imap-smtp-caldav-connection/services/imap-smtp-caldav-connection-validator.service';
 import { ImapSmtpCaldavService } from 'src/engine/core-modules/imap-smtp-caldav-connection/services/imap-smtp-caldav-connection.service';
 import { type ConnectionParameters } from 'src/engine/core-modules/imap-smtp-caldav-connection/types/imap-smtp-caldav-connection.type';
@@ -10,11 +12,20 @@ import { TwentyConfigService } from 'src/engine/core-modules/twenty-config/twent
 import { CalDavClientService } from 'src/modules/calendar/calendar-event-import-manager/drivers/caldav/services/caldav-client.service';
 import { CalDavFetchEventsService } from 'src/modules/calendar/calendar-event-import-manager/drivers/caldav/services/caldav-fetch-events.service';
 
+jest.mock('nodemailer', () => ({
+  createTransport: jest.fn(),
+}));
+
 describe('ImapSmtpCaldavService', () => {
   let service: ImapSmtpCaldavService;
 
   const mockClient = {} as DAVClient;
 
+  const mockVerify = jest.fn().mockResolvedValue(true);
+  const mockGetValidatedHost = jest
+    .fn()
+    .mockImplementation((host: string) => Promise.resolve(host));
+
   const mockCalDavClientService = {
     getClient: jest.fn(),
   };
@@ -25,6 +36,8 @@ describe('ImapSmtpCaldavService', () => {
 
   beforeEach(async () => {
     jest.clearAllMocks();
+    (createTransport as jest.Mock).mockReturnValue({ verify: mockVerify });
+    mockVerify.mockResolvedValue(true);
     mockCalDavClientService.getClient.mockResolvedValue(mockClient);
     mockCalDavFetchEventsService.listEventCalendars.mockResolvedValue([
       { url: 'https://caldav.example.com/calendars/user/default/' },
@@ -33,7 +46,10 @@ describe('ImapSmtpCaldavService', () => {
     const module: TestingModule = await Test.createTestingModule({
       providers: [
         ImapSmtpCaldavService,
-        { provide: SecureHttpClientService, useValue: {} },
+        {
+          provide: SecureHttpClientService,
+          useValue: { getValidatedHost: mockGetValidatedHost },
+        },
         { provide: ImapSmtpCaldavValidatorService, useValue: {} },
         {
           provide: TwentyConfigService,
@@ -59,6 +75,7 @@ describe('ImapSmtpCaldavService', () => {
       port: 443,
       username: 'user@example.com',
       password: 'password123',
+      connectionSecurity: EmailConnectionSecurity.SSL_TLS,
     };
 
     it('builds a CalDAV client and lists its event calendars', async () => {
@@ -93,4 +110,48 @@ describe('ImapSmtpCaldavService', () => {
       ).rejects.toThrow('No calendar with event support found');
     });
   });
+
+  describe('testSmtpConnection', () => {
+    const params: ConnectionParameters = {
+      host: 'smtp.example.com',
+      port: 587,
+      username: 'user@example.com',
+      password: 'password123',
+      connectionSecurity: EmailConnectionSecurity.STARTTLS,
+    };
+
+    it('uses implicit TLS when connectionSecurity is SSL_TLS', async () => {
+      await service.testSmtpConnection('user@example.com', {
+        ...params,
+        port: 465,
+        connectionSecurity: EmailConnectionSecurity.SSL_TLS,
+      });
+
+      expect(createTransport).toHaveBeenCalledWith(
+        expect.objectContaining({ secure: true }),
+      );
+    });
+
+    it('upgrades opportunistically via STARTTLS', async () => {
+      await service.testSmtpConnection('user@example.com', {
+        ...params,
+        connectionSecurity: EmailConnectionSecurity.STARTTLS,
+      });
+
+      expect(createTransport).toHaveBeenCalledWith(
+        expect.objectContaining({ secure: false }),
+      );
+    });
+
+    it('disables TLS when connectionSecurity is NONE', async () => {
+      await service.testSmtpConnection('user@example.com', {
+        ...params,
+        connectionSecurity: EmailConnectionSecurity.NONE,
+      });
+
+      expect(createTransport).toHaveBeenCalledWith(
+        expect.objectContaining({ secure: false, ignoreTLS: true }),
+      );
+    });
+  });
 });
diff --git a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/services/imap-smtp-caldav-connection.service.ts b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/services/imap-smtp-caldav-connection.service.ts
index 03d762913b..8c9e279124 100644
--- a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/services/imap-smtp-caldav-connection.service.ts
+++ b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/services/imap-smtp-caldav-connection.service.ts
@@ -14,6 +14,8 @@ import {
   type ConnectionParameters,
   type PlaintextImapSmtpCaldavParams,
 } from 'src/engine/core-modules/imap-smtp-caldav-connection/types/imap-smtp-caldav-connection.type';
+import { buildImapTlsOptions } from 'src/engine/core-modules/imap-smtp-caldav-connection/utils/build-imap-tls-options.util';
+import { buildSmtpTlsOptions } from 'src/engine/core-modules/imap-smtp-caldav-connection/utils/build-smtp-tls-options.util';
 import { SecureHttpClientService } from 'src/engine/core-modules/secure-http-client/secure-http-client.service';
 import { TwentyConfigService } from 'src/engine/core-modules/twenty-config/twenty-config.service';
 import { CalDavClientService } from 'src/modules/calendar/calendar-event-import-manager/drivers/caldav/services/caldav-client.service';
@@ -41,7 +43,7 @@ export class ImapSmtpCaldavService {
     const client = new ImapFlow({
       host: validatedHost,
       port: params.port,
-      secure: params.secure ?? true,
+      ...buildImapTlsOptions(params.connectionSecurity),
       auth: {
         user: params.username ?? handle,
         pass: params.password,
@@ -114,6 +116,7 @@ export class ImapSmtpCaldavService {
     const transport = createTransport({
       host: validatedHost,
       port: params.port,
+      ...buildSmtpTlsOptions(params.connectionSecurity),
       auth: {
         user: params.username ?? handle,
         pass: params.password,
diff --git a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/types/imap-smtp-caldav-connection.type.ts b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/types/imap-smtp-caldav-connection.type.ts
index 7be1c1ce20..37923774b6 100644
--- a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/types/imap-smtp-caldav-connection.type.ts
+++ b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/types/imap-smtp-caldav-connection.type.ts
@@ -24,6 +24,8 @@ export type ConnectionParametersUpdate<Pwd extends string = string> = Omit<
 
 export type AccountType = (typeof ACCOUNT_TYPES)[number];
 
+export { EmailConnectionSecurity } from 'src/engine/core-modules/imap-smtp-caldav-connection/enums/email-connection-security.enum';
+
 export type ImapSmtpCaldavParams<Pwd extends string = string> = {
   IMAP?: ConnectionParameters<Pwd>;
   SMTP?: ConnectionParameters<Pwd>;
diff --git a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/utils/__tests__/build-imap-tls-options.util.spec.ts b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/utils/__tests__/build-imap-tls-options.util.spec.ts
new file mode 100644
index 0000000000..9a3cf4d62f
--- /dev/null
+++ b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/utils/__tests__/build-imap-tls-options.util.spec.ts
@@ -0,0 +1,23 @@
+import { EmailConnectionSecurity } from 'src/engine/core-modules/imap-smtp-caldav-connection/enums/email-connection-security.enum';
+import { buildImapTlsOptions } from 'src/engine/core-modules/imap-smtp-caldav-connection/utils/build-imap-tls-options.util';
+
+describe('buildImapTlsOptions', () => {
+  it('negotiates TLS at connection time for SSL_TLS', () => {
+    expect(buildImapTlsOptions(EmailConnectionSecurity.SSL_TLS)).toEqual({
+      secure: true,
+    });
+  });
+
+  it('upgrades opportunistically via STARTTLS when the server offers it', () => {
+    expect(buildImapTlsOptions(EmailConnectionSecurity.STARTTLS)).toEqual({
+      secure: false,
+    });
+  });
+
+  it('forces plaintext for NONE by disabling the STARTTLS upgrade', () => {
+    expect(buildImapTlsOptions(EmailConnectionSecurity.NONE)).toEqual({
+      secure: false,
+      doSTARTTLS: false,
+    });
+  });
+});
diff --git a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/utils/__tests__/build-smtp-tls-options.util.spec.ts b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/utils/__tests__/build-smtp-tls-options.util.spec.ts
new file mode 100644
index 0000000000..23f6cda5ad
--- /dev/null
+++ b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/utils/__tests__/build-smtp-tls-options.util.spec.ts
@@ -0,0 +1,23 @@
+import { EmailConnectionSecurity } from 'src/engine/core-modules/imap-smtp-caldav-connection/enums/email-connection-security.enum';
+import { buildSmtpTlsOptions } from 'src/engine/core-modules/imap-smtp-caldav-connection/utils/build-smtp-tls-options.util';
+
+describe('buildSmtpTlsOptions', () => {
+  it('negotiates TLS at connection time for SSL_TLS', () => {
+    expect(buildSmtpTlsOptions(EmailConnectionSecurity.SSL_TLS)).toEqual({
+      secure: true,
+    });
+  });
+
+  it('upgrades opportunistically via STARTTLS when the server offers it', () => {
+    expect(buildSmtpTlsOptions(EmailConnectionSecurity.STARTTLS)).toEqual({
+      secure: false,
+    });
+  });
+
+  it('forces plaintext for NONE by skipping the STARTTLS upgrade entirely', () => {
+    expect(buildSmtpTlsOptions(EmailConnectionSecurity.NONE)).toEqual({
+      secure: false,
+      ignoreTLS: true,
+    });
+  });
+});
diff --git a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/utils/build-imap-tls-options.util.ts b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/utils/build-imap-tls-options.util.ts
new file mode 100644
index 0000000000..be58f93f8a
--- /dev/null
+++ b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/utils/build-imap-tls-options.util.ts
@@ -0,0 +1,19 @@
+import { EmailConnectionSecurity } from 'src/engine/core-modules/imap-smtp-caldav-connection/enums/email-connection-security.enum';
+
+type ImapTlsOptions = {
+  secure: boolean;
+  doSTARTTLS?: boolean;
+};
+
+export const buildImapTlsOptions = (
+  connectionSecurity: EmailConnectionSecurity,
+): ImapTlsOptions => {
+  switch (connectionSecurity) {
+    case EmailConnectionSecurity.SSL_TLS:
+      return { secure: true };
+    case EmailConnectionSecurity.STARTTLS:
+      return { secure: false };
+    case EmailConnectionSecurity.NONE:
+      return { secure: false, doSTARTTLS: false };
+  }
+};
diff --git a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/utils/build-public-connection-parameters.util.ts b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/utils/build-public-connection-parameters.util.ts
index 7bd8ce9e03..f0f566e27c 100644
--- a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/utils/build-public-connection-parameters.util.ts
+++ b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/utils/build-public-connection-parameters.util.ts
@@ -1,13 +1,16 @@
 import { ACCOUNT_TYPES } from 'twenty-shared/constants';
 import { isDefined } from 'twenty-shared/utils';
 
-import { type ImapSmtpCaldavParams } from 'src/engine/core-modules/imap-smtp-caldav-connection/types/imap-smtp-caldav-connection.type';
+import {
+  type EmailConnectionSecurity,
+  type ImapSmtpCaldavParams,
+} from 'src/engine/core-modules/imap-smtp-caldav-connection/types/imap-smtp-caldav-connection.type';
 
 type PublicConnectionParams = {
   host: string;
   port: number;
   username?: string;
-  secure?: boolean;
+  connectionSecurity?: EmailConnectionSecurity;
 };
 
 type PublicConnectionParameters = {
diff --git a/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/utils/build-smtp-tls-options.util.ts b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/utils/build-smtp-tls-options.util.ts
new file mode 100644
index 0000000000..fa6fd8af77
--- /dev/null
+++ b/packages/twenty-server/src/engine/core-modules/imap-smtp-caldav-connection/utils/build-smtp-tls-options.util.ts
@@ -0,0 +1,19 @@
+import { EmailConnectionSecurity } from 'src/engine/core-modules/imap-smtp-caldav-connection/enums/email-connection-security.enum';
+
+type SmtpTlsOptions = {
+  secure: boolean;
+  ignoreTLS?: boolean;
+};
+
+export const buildSmtpTlsOptions = (
+  connectionSecurity: EmailConnectionSecurity,
+): SmtpTlsOptions => {
+  switch (connectionSecurity) {
+    case EmailConnectionSecurity.SSL_TLS:
+      return { secure: true };
+    case EmailConnectionSecurity.STARTTLS:
+      return { secure: false };
+    case EmailConnectionSecurity.NONE:
+      return { secure: false, ignoreTLS: true };
+  }
+};
diff --git a/packages/twenty-server/src/engine/metadata-modules/connected-account/dtos/connected-account-public.dto.ts b/packages/twenty-server/src/engine/metadata-modules/connected-account/dtos/connected-account-public.dto.ts
index 78a72c3ee4..a915d7a724 100644
--- a/packages/twenty-server/src/engine/metadata-modules/connected-account/dtos/connected-account-public.dto.ts
+++ b/packages/twenty-server/src/engine/metadata-modules/connected-account/dtos/connected-account-public.dto.ts
@@ -2,6 +2,7 @@ import { Field, ObjectType, OmitType } from '@nestjs/graphql';
 
 import { IsOptional } from 'class-validator';
 
+import { EmailConnectionSecurity } from 'src/engine/core-modules/imap-smtp-caldav-connection/enums/email-connection-security.enum';
 import { ConnectedAccountDTO } from 'src/engine/metadata-modules/connected-account/dtos/connected-account.dto';
 
 @ObjectType('PublicConnectionParametersOutput')
@@ -15,8 +16,8 @@ class PublicConnectionParametersDTO {
   @Field(() => String, { nullable: true })
   username?: string;
 
-  @Field(() => Boolean, { nullable: true })
-  secure?: boolean;
+  @Field(() => EmailConnectionSecurity, { nullable: true })
+  connectionSecurity?: EmailConnectionSecurity;
 }
 
 @ObjectType('PublicImapSmtpCaldavConnectionParameters')
diff --git a/packages/twenty-server/src/modules/connected-account/services/imap-smtp-caldav-apis.service.spec.ts b/packages/twenty-server/src/modules/connected-account/services/imap-smtp-caldav-apis.service.spec.ts
index d61e333474..b9eb2b58f2 100644
--- a/packages/twenty-server/src/modules/connected-account/services/imap-smtp-caldav-apis.service.spec.ts
+++ b/packages/twenty-server/src/modules/connected-account/services/imap-smtp-caldav-apis.service.spec.ts
@@ -245,13 +245,13 @@ describe('ImapSmtpCalDavAPIService', () => {
         IMAP: {
           host: 'imap.example.com',
           port: 993,
-          secure: true,
+          connectionSecurity: 'SSL_TLS',
           password: 'password' as PlaintextString,
         },
         SMTP: {
           host: 'smtp.example.com',
           port: 587,
-          secure: true,
+          connectionSecurity: 'SSL_TLS',
           username: 'test@example.com',
           password: 'password' as PlaintextString,
         },
@@ -342,7 +342,7 @@ describe('ImapSmtpCalDavAPIService', () => {
           CALDAV: {
             host: 'caldav.example.com',
             port: 443,
-            secure: true,
+            connectionSecurity: 'SSL_TLS',
             username: 'test@example.com',
             password: 'password' as PlaintextString,
           },
@@ -472,7 +472,7 @@ describe('ImapSmtpCalDavAPIService', () => {
           IMAP: {
             host: 'imap.example.com',
             port: 993,
-            secure: true,
+            connectionSecurity: 'SSL_TLS',
             password: 'password' as PlaintextString,
           },
         } as PlaintextImapSmtpCaldavParams,
@@ -507,7 +507,7 @@ describe('ImapSmtpCalDavAPIService', () => {
           CALDAV: {
             host: 'caldav.example.com',
             port: 443,
-            secure: true,
+            connectionSecurity: 'SSL_TLS',
             username: 'test@example.com',
             password: 'password' as PlaintextString,
           },
@@ -543,13 +543,13 @@ describe('ImapSmtpCalDavAPIService', () => {
           IMAP: {
             host: 'imap.example.com',
             port: 993,
-            secure: true,
+            connectionSecurity: 'SSL_TLS',
             password: 'password' as PlaintextString,
           },
           SMTP: {
             host: 'smtp.example.com',
             port: 587,
-            secure: true,
+            connectionSecurity: 'SSL_TLS',
             username: 'test@example.com',
             password: 'password' as PlaintextString,
           },
@@ -585,20 +585,20 @@ describe('ImapSmtpCalDavAPIService', () => {
           IMAP: {
             host: 'imap.example.com',
             port: 993,
-            secure: true,
+            connectionSecurity: 'SSL_TLS',
             password: 'password' as PlaintextString,
           },
           SMTP: {
             host: 'smtp.example.com',
             port: 587,
-            secure: true,
+            connectionSecurity: 'SSL_TLS',
             username: 'test@example.com',
             password: 'password' as PlaintextString,
           },
           CALDAV: {
             host: 'caldav.example.com',
             port: 443,
-            secure: true,
+            connectionSecurity: 'SSL_TLS',
             username: 'test@example.com',
             password: 'password' as PlaintextString,
           },
@@ -680,7 +680,7 @@ describe('ImapSmtpCalDavAPIService', () => {
           SMTP: {
             host: 'smtp.example.com',
             port: 587,
-            secure: true,
+            connectionSecurity: 'SSL_TLS',
             username: 'test@example.com',
             password: 'password' as PlaintextString,
           },
diff --git a/packages/twenty-server/src/modules/messaging/message-import-manager/drivers/imap/providers/imap-client.provider.ts b/packages/twenty-server/src/modules/messaging/message-import-manager/drivers/imap/providers/imap-client.provider.ts
index cb62b7a7da..0f88066b11 100644
--- a/packages/twenty-server/src/modules/messaging/message-import-manager/drivers/imap/providers/imap-client.provider.ts
+++ b/packages/twenty-server/src/modules/messaging/message-import-manager/drivers/imap/providers/imap-client.provider.ts
@@ -6,6 +6,7 @@ import { ConnectedAccountProvider } from 'twenty-shared/types';
 import { isDefined } from 'twenty-shared/utils';
 import { Repository } from 'typeorm';
 
+import { buildImapTlsOptions } from 'src/engine/core-modules/imap-smtp-caldav-connection/utils/build-imap-tls-options.util';
 import { SecureHttpClientService } from 'src/engine/core-modules/secure-http-client/secure-http-client.service';
 import { ConnectedAccountEntity } from 'src/engine/metadata-modules/connected-account/entities/connected-account.entity';
 import { ConnectedAccountTokenEncryptionService } from 'src/engine/metadata-modules/connected-account/services/connected-account-token-encryption.service';
@@ -94,7 +95,7 @@ export class ImapClientProvider {
     const client = new ImapFlow({
       host: validatedImapHost,
       port: imapParams.port || 993,
-      secure: imapParams.secure,
+      ...buildImapTlsOptions(imapParams.connectionSecurity),
       auth: {
         user: isDefined(imapParams.username)
           ? imapParams.username
diff --git a/packages/twenty-server/src/modules/messaging/message-import-manager/drivers/smtp/providers/smtp-client.provider.ts b/packages/twenty-server/src/modules/messaging/message-import-manager/drivers/smtp/providers/smtp-client.provider.ts
index bf4f750fa3..a979ebe29f 100644
--- a/packages/twenty-server/src/modules/messaging/message-import-manager/drivers/smtp/providers/smtp-client.provider.ts
+++ b/packages/twenty-server/src/modules/messaging/message-import-manager/drivers/smtp/providers/smtp-client.provider.ts
@@ -9,6 +9,7 @@ import { ConnectedAccountProvider } from 'twenty-shared/types';
 import { isDefined } from 'twenty-shared/utils';
 import { Repository } from 'typeorm';
 
+import { buildSmtpTlsOptions } from 'src/engine/core-modules/imap-smtp-caldav-connection/utils/build-smtp-tls-options.util';
 import { SecureHttpClientService } from 'src/engine/core-modules/secure-http-client/secure-http-client.service';
 import { ConnectedAccountEntity } from 'src/engine/metadata-modules/connected-account/entities/connected-account.entity';
 import { ConnectedAccountTokenEncryptionService } from 'src/engine/metadata-modules/connected-account/services/connected-account-token-encryption.service';
@@ -52,6 +53,7 @@ export class SmtpClientProvider {
     const options: SMTPConnection.Options = {
       host: validatedSmtpHost,
       port: smtpParams.port,
+      ...buildSmtpTlsOptions(smtpParams.connectionSecurity),
       auth: {
         user: smtpParams.username ?? connectedAccount.handle ?? '',
         pass: smtpParams.password,
diff --git a/packages/twenty-server/test/integration/metadata/suites/connected-account/failing-save-imap-smtp-caldav-account.integration-spec.ts b/packages/twenty-server/test/integration/metadata/suites/connected-account/failing-save-imap-smtp-caldav-account.integration-spec.ts
index 4b8f0e2a36..c245b8bfa9 100644
--- a/packages/twenty-server/test/integration/metadata/suites/connected-account/failing-save-imap-smtp-caldav-account.integration-spec.ts
+++ b/packages/twenty-server/test/integration/metadata/suites/connected-account/failing-save-imap-smtp-caldav-account.integration-spec.ts
@@ -5,30 +5,22 @@ import {
   type EachTestingContext,
 } from 'twenty-shared/testing';
 
+import { EmailConnectionSecurity } from 'src/engine/core-modules/imap-smtp-caldav-connection/enums/email-connection-security.enum';
+
+type ProtocolConnectionContext = {
+  host: string;
+  port: number;
+  username?: string;
+  password?: string;
+  connectionSecurity?: EmailConnectionSecurity;
+};
+
 type TestContext = {
   handle: string;
   connectionParameters: {
-    IMAP?: {
-      host: string;
-      port: number;
-      username?: string;
-      password?: string;
-      secure?: boolean;
-    };
-    SMTP?: {
-      host: string;
-      port: number;
-      username?: string;
-      password?: string;
-      secure?: boolean;
-    };
-    CALDAV?: {
-      host: string;
-      port: number;
-      username?: string;
-      password?: string;
-      secure?: boolean;
-    };
+    IMAP?: ProtocolConnectionContext;
+    SMTP?: ProtocolConnectionContext;
+    CALDAV?: ProtocolConnectionContext;
   };
   id?: string;
 };
@@ -48,7 +40,7 @@ describe('Connected account creation should fail', () => {
             host: 'imap.example.com',
             port: 993,
             username: 'user@example.com',
-            secure: true,
+            connectionSecurity: EmailConnectionSecurity.SSL_TLS,
           },
         },
       },
@@ -62,7 +54,7 @@ describe('Connected account creation should fail', () => {
             host: 'smtp.example.com',
             port: 465,
             username: 'user@example.com',
-            secure: true,
+            connectionSecurity: EmailConnectionSecurity.SSL_TLS,
           },
         },
       },
@@ -76,7 +68,7 @@ describe('Connected account creation should fail', () => {
             host: 'caldav.example.com',
             port: 443,
             username: 'user@example.com',
-            secure: true,
+            connectionSecurity: EmailConnectionSecurity.SSL_TLS,
           },
         },
       },
@@ -90,7 +82,7 @@ describe('Connected account creation should fail', () => {
             host: '',
             port: 993,
             password: 'secret',
-            secure: true,
+            connectionSecurity: EmailConnectionSecurity.SSL_TLS,
           },
         },
       },
@@ -104,7 +96,7 @@ describe('Connected account creation should fail', () => {
             host: 'imap.example.com',
             port: 0,
             password: 'secret',
-            secure: true,
+            connectionSecurity: EmailConnectionSecurity.SSL_TLS,
           },
         },
       },
@@ -118,7 +110,7 @@ describe('Connected account creation should fail', () => {
             host: 'imap.example.com',
             port: 993,
             password: '',
-            secure: true,
+            connectionSecurity: EmailConnectionSecurity.SSL_TLS,
           },
         },
       },
diff --git a/packages/twenty-server/test/integration/metadata/suites/connected-account/successful-save-imap-smtp-caldav-account.integration-spec.ts b/packages/twenty-server/test/integration/metadata/suites/connected-account/successful-save-imap-smtp-caldav-account.integration-spec.ts
index 0743d678e8..a00b6ce236 100644
--- a/packages/twenty-server/test/integration/metadata/suites/connected-account/successful-save-imap-smtp-caldav-account.integration-spec.ts
+++ b/packages/twenty-server/test/integration/metadata/suites/connected-account/successful-save-imap-smtp-caldav-account.integration-spec.ts
@@ -2,6 +2,8 @@ import { deleteConnectedAccount } from 'test/integration/metadata/suites/connect
 import { getConnectedImapSmtpCaldavAccount } from 'test/integration/metadata/suites/connected-account/utils/get-connected-imap-smtp-caldav-account.util';
 import { saveImapSmtpCaldavAccount } from 'test/integration/metadata/suites/connected-account/utils/save-imap-smtp-caldav-account.util';
 
+import { EmailConnectionSecurity } from 'src/engine/core-modules/imap-smtp-caldav-connection/enums/email-connection-security.enum';
+
 const createAccount = async (handle: string): Promise<string> => {
   const { data } = await saveImapSmtpCaldavAccount({
     expectToFail: false,
@@ -13,14 +15,14 @@ const createAccount = async (handle: string): Promise<string> => {
           port: 993,
           username: 'user@example.com',
           password: 'test-password',
-          secure: true,
+          connectionSecurity: EmailConnectionSecurity.SSL_TLS,
         },
         SMTP: {
           host: 'smtp.fastmail.com',
           port: 465,
           username: 'user@example.com',
           password: 'test-password',
-          secure: true,
+          connectionSecurity: EmailConnectionSecurity.SSL_TLS,
         },
       },
     },
@@ -49,14 +51,14 @@ describe('Successful save IMAP/SMTP/CALDAV account', () => {
             port: 993,
             username: 'user@example.com',
             password: 'test-password',
-            secure: true,
+            connectionSecurity: EmailConnectionSecurity.SSL_TLS,
           },
           SMTP: {
             host: 'smtp.fastmail.com',
             port: 465,
             username: 'user@example.com',
             password: 'test-password',
-            secure: true,
+            connectionSecurity: EmailConnectionSecurity.SSL_TLS,
           },
         },
       },
@@ -78,13 +80,13 @@ describe('Successful save IMAP/SMTP/CALDAV account', () => {
         host: 'imap.fastmail.com',
         port: 993,
         username: 'user@example.com',
-        secure: true,
+        connectionSecurity: EmailConnectionSecurity.SSL_TLS,
       },
       SMTP: {
         host: 'smtp.fastmail.com',
         port: 465,
         username: 'user@example.com',
-        secure: true,
+        connectionSecurity: EmailConnectionSecurity.SSL_TLS,
       },
       CALDAV: null,
     });
@@ -104,13 +106,13 @@ describe('Successful save IMAP/SMTP/CALDAV account', () => {
             host: 'imap-updated.fastmail.com',
             port: 993,
             username: 'updated-user@example.com',
-            secure: true,
+            connectionSecurity: EmailConnectionSecurity.SSL_TLS,
           },
           SMTP: {
             host: 'smtp-updated.fastmail.com',
             port: 587,
             username: 'updated-user@example.com',
-            secure: false,
+            connectionSecurity: EmailConnectionSecurity.STARTTLS,
           },
         },
         id: accountId,
@@ -129,13 +131,13 @@ describe('Successful save IMAP/SMTP/CALDAV account', () => {
         host: 'imap-updated.fastmail.com',
         port: 993,
         username: 'updated-user@example.com',
-        secure: true,
+        connectionSecurity: EmailConnectionSecurity.SSL_TLS,
       },
       SMTP: {
         host: 'smtp-updated.fastmail.com',
         port: 587,
         username: 'updated-user@example.com',
-        secure: false,
+        connectionSecurity: EmailConnectionSecurity.STARTTLS,
       },
       CALDAV: null,
     });
@@ -156,7 +158,7 @@ describe('Successful save IMAP/SMTP/CALDAV account', () => {
             port: 993,
             username: 'user@example.com',
             password: 'test-password',
-            secure: true,
+            connectionSecurity: EmailConnectionSecurity.SSL_TLS,
           },
         },
         id: accountId,
@@ -175,7 +177,7 @@ describe('Successful save IMAP/SMTP/CALDAV account', () => {
         host: 'imap.fastmail.com',
         port: 993,
         username: 'user@example.com',
-        secure: true,
+        connectionSecurity: EmailConnectionSecurity.SSL_TLS,
       },
       SMTP: null,
       CALDAV: null,
@@ -197,14 +199,14 @@ describe('Successful save IMAP/SMTP/CALDAV account', () => {
             port: 993,
             username: 'user@example.com',
             password: 'new-password',
-            secure: true,
+            connectionSecurity: EmailConnectionSecurity.SSL_TLS,
           },
           SMTP: {
             host: 'smtp.fastmail.com',
             port: 465,
             username: 'user@example.com',
             password: 'new-password',
-            secure: true,
+            connectionSecurity: EmailConnectionSecurity.SSL_TLS,
           },
         },
         id: accountId,
@@ -223,13 +225,13 @@ describe('Successful save IMAP/SMTP/CALDAV account', () => {
         host: 'imap.fastmail.com',
         port: 993,
         username: 'user@example.com',
-        secure: true,
+        connectionSecurity: EmailConnectionSecurity.SSL_TLS,
       },
       SMTP: {
         host: 'smtp.fastmail.com',
         port: 465,
         username: 'user@example.com',
-        secure: true,
+        connectionSecurity: EmailConnectionSecurity.SSL_TLS,
       },
       CALDAV: null,
     });
diff --git a/packages/twenty-server/test/integration/metadata/suites/connected-account/utils/get-connected-imap-smtp-caldav-account.util.ts b/packages/twenty-server/test/integration/metadata/suites/connected-account/utils/get-connected-imap-smtp-caldav-account.util.ts
index 3304d18206..4586cc45b6 100644
--- a/packages/twenty-server/test/integration/metadata/suites/connected-account/utils/get-connected-imap-smtp-caldav-account.util.ts
+++ b/packages/twenty-server/test/integration/metadata/suites/connected-account/utils/get-connected-imap-smtp-caldav-account.util.ts
@@ -19,19 +19,19 @@ export const getConnectedImapSmtpCaldavAccount = async ({
               host
               port
               username
-              secure
+              connectionSecurity
             }
             SMTP {
               host
               port
               username
-              secure
+              connectionSecurity
             }
             CALDAV {
               host
               port
               username
-              secure
+              connectionSecurity
             }
           }
         }
diff --git a/packages/twenty-server/test/integration/metadata/suites/connected-account/utils/save-imap-smtp-caldav-account.util.ts b/packages/twenty-server/test/integration/metadata/suites/connected-account/utils/save-imap-smtp-caldav-account.util.ts
index d790f2a109..de5c88ba61 100644
--- a/packages/twenty-server/test/integration/metadata/suites/connected-account/utils/save-imap-smtp-caldav-account.util.ts
+++ b/packages/twenty-server/test/integration/metadata/suites/connected-account/utils/save-imap-smtp-caldav-account.util.ts
@@ -1,30 +1,22 @@
 import { gql } from 'graphql-tag';
 import { makeMetadataAPIRequest } from 'test/integration/metadata/suites/utils/make-metadata-api-request.util';
 
+import { EmailConnectionSecurity } from 'src/engine/core-modules/imap-smtp-caldav-connection/enums/email-connection-security.enum';
+
+type ProtocolConnectionInput = {
+  host: string;
+  port: number;
+  username?: string;
+  password?: string;
+  connectionSecurity?: EmailConnectionSecurity;
+};
+
 type SaveImapSmtpCaldavAccountInput = {
   handle: string;
   connectionParameters: {
-    IMAP?: {
-      host: string;
-      port: number;
-      username?: string;
-      password?: string;
-      secure?: boolean;
-    };
-    SMTP?: {
-      host: string;
-      port: number;
-      username?: string;
-      password?: string;
-      secure?: boolean;
-    };
-    CALDAV?: {
-      host: string;
-      port: number;
-      username?: string;
-      password?: string;
-      secure?: boolean;
-    };
+    IMAP?: ProtocolConnectionInput;
+    SMTP?: ProtocolConnectionInput;
+    CALDAV?: ProtocolConnectionInput;
   };
   id?: string;
 };
diff --git a/packages/twenty-server/test/integration/secret-encryption/connection-parameters-rotation.integration-spec.ts b/packages/twenty-server/test/integration/secret-encryption/connection-parameters-rotation.integration-spec.ts
index 0dc7144a8b..e5525574f5 100644
--- a/packages/twenty-server/test/integration/secret-encryption/connection-parameters-rotation.integration-spec.ts
+++ b/packages/twenty-server/test/integration/secret-encryption/connection-parameters-rotation.integration-spec.ts
@@ -6,6 +6,7 @@ import { saveImapSmtpCaldavAccount } from 'test/integration/metadata/suites/conn
 import { runSecretEncryptionRotationCommand } from 'test/integration/secret-encryption/utils/run-secret-encryption-rotation-command.util';
 import { buildSecretEncryptionServiceFromEnv } from 'test/integration/upgrade/utils/build-secret-encryption-service.util';
 
+import { EmailConnectionSecurity } from 'src/engine/core-modules/imap-smtp-caldav-connection/enums/email-connection-security.enum';
 import { type EncryptedImapSmtpCaldavParams } from 'src/engine/core-modules/imap-smtp-caldav-connection/types/imap-smtp-caldav-connection.type';
 import { type SecretEncryptionService } from 'src/engine/core-modules/secret-encryption/secret-encryption.service';
 
@@ -53,12 +54,9 @@ const expectAllPasswordsDecryptTo = ({
     expect(params).toBeDefined();
     expect(params?.password).toMatch(V2_ENVELOPE_REGEX);
 
-    const decrypted = secretEncryption.decryptVersioned(
-      params!.password,
-      {
-        workspaceId: row.workspaceId,
-      },
-    );
+    const decrypted = secretEncryption.decryptVersioned(params!.password, {
+      workspaceId: row.workspaceId,
+    });
 
     expect(decrypted).toBe(expectedPlaintextByProtocol[protocol]);
   }
@@ -83,21 +81,21 @@ describe('secret-encryption:rotate command — connection-parameters site (integ
             port: 993,
             username: 'rotation@example.com',
             password: IMAP_PASSWORD,
-            secure: true,
+            connectionSecurity: EmailConnectionSecurity.SSL_TLS,
           },
           SMTP: {
             host: 'smtp.fastmail.com',
             port: 465,
             username: 'rotation@example.com',
             password: SMTP_PASSWORD,
-            secure: true,
+            connectionSecurity: EmailConnectionSecurity.SSL_TLS,
           },
           CALDAV: {
             host: 'caldav.fastmail.com',
             port: 443,
             username: 'rotation@example.com',
             password: CALDAV_PASSWORD,
-            secure: true,
+            connectionSecurity: EmailConnectionSecurity.SSL_TLS,
           },
         },
       },
diff --git a/packages/twenty-server/test/integration/upgrade/suites/2-15-instance-command-slow-1781461753981-backfill-connection-security.integration-spec.ts b/packages/twenty-server/test/integration/upgrade/suites/2-15-instance-command-slow-1781461753981-backfill-connection-security.integration-spec.ts
new file mode 100644
index 0000000000..2e748e7c46
--- /dev/null
+++ b/packages/twenty-server/test/integration/upgrade/suites/2-15-instance-command-slow-1781461753981-backfill-connection-security.integration-spec.ts
@@ -0,0 +1,189 @@
+import { config } from 'dotenv';
+import { isDefined } from 'twenty-shared/utils';
+import { DataSource } from 'typeorm';
+
+import { BackfillConnectionSecuritySlowInstanceCommand } from 'src/database/commands/upgrade-version-command/2-15/2-15-instance-command-slow-1781461753981-backfill-connection-security';
+
+jest.useRealTimers();
+
+config({
+  path: process.env.NODE_ENV === 'test' ? '.env.test' : '.env',
+  override: true,
+});
+
+const TEST_ROW_HANDLE_PREFIX = 'backfill-connection-security-test-';
+
+describe('BackfillConnectionSecuritySlowInstanceCommand (integration)', () => {
+  let dataSource: DataSource;
+  let command: BackfillConnectionSecuritySlowInstanceCommand;
+  let workspaceId: string;
+  let userWorkspaceId: string;
+  const seededRowIds: string[] = [];
+
+  const seedAccount = async (
+    connectionParameters: Record<string, unknown>,
+  ): Promise<string> => {
+    const [row] = await dataSource.query(
+      `INSERT INTO "core"."connectedAccount"
+         ("handle", "provider", "userWorkspaceId", "workspaceId", "visibility", "connectionParameters")
+       VALUES ($1, 'imap_smtp_caldav', $2, $3, 'user', $4)
+       RETURNING id`,
+      [
+        `${TEST_ROW_HANDLE_PREFIX}${seededRowIds.length}`,
+        userWorkspaceId,
+        workspaceId,
+        JSON.stringify(connectionParameters),
+      ],
+    );
+
+    seededRowIds.push(row.id as string);
+
+    return row.id as string;
+  };
+
+  const getConnectionParameters = async (
+    id: string,
+  ): Promise<Record<string, Record<string, unknown>>> => {
+    const [row] = await dataSource.query(
+      `SELECT "connectionParameters" FROM "core"."connectedAccount" WHERE id = $1`,
+      [id],
+    );
+
+    return row.connectionParameters;
+  };
+
+  beforeAll(async () => {
+    dataSource = new DataSource({
+      type: 'postgres',
+      url: process.env.PG_DATABASE_URL,
+      schema: 'core',
+      entities: [],
+      synchronize: false,
+    });
+    await dataSource.initialize();
+
+    command = new BackfillConnectionSecuritySlowInstanceCommand();
+
+    const [seedWorkspaceRow] = await dataSource.query(
+      `SELECT uw.id AS "userWorkspaceId", uw."workspaceId" AS "workspaceId"
+         FROM "core"."userWorkspace" uw
+         LIMIT 1`,
+    );
+
+    if (!isDefined(seedWorkspaceRow)) {
+      throw new Error(
+        'No seeded userWorkspace row found; run database:reset before the integration suite.',
+      );
+    }
+
+    userWorkspaceId = seedWorkspaceRow.userWorkspaceId;
+    workspaceId = seedWorkspaceRow.workspaceId;
+  }, 30000);
+
+  afterEach(async () => {
+    if (seededRowIds.length > 0) {
+      await dataSource.query(
+        `DELETE FROM "core"."connectedAccount" WHERE id = ANY($1::uuid[])`,
+        [seededRowIds],
+      );
+      seededRowIds.length = 0;
+    }
+  });
+
+  afterAll(async () => {
+    await dataSource?.destroy();
+  });
+
+  it('maps every legacy protocol to the mode matching its prior on-wire behavior and drops the secure key', async () => {
+    const id = await seedAccount({
+      IMAP: {
+        host: 'imap.example.com',
+        port: 993,
+        secure: true,
+        password: 'enc:v2:x',
+      },
+      SMTP: {
+        host: 'smtp.example.com',
+        port: 587,
+        secure: true,
+        password: 'enc:v2:x',
+      },
+      CALDAV: {
+        host: 'https://dav.example.com',
+        port: 443,
+        secure: true,
+        password: 'enc:v2:x',
+      },
+    });
+
+    await command.runDataMigration(dataSource);
+
+    const params = await getConnectionParameters(id);
+
+    expect(params.IMAP.connectionSecurity).toBe('SSL_TLS');
+    expect(params.SMTP.connectionSecurity).toBe('STARTTLS');
+    expect(params.CALDAV.connectionSecurity).toBe('SSL_TLS');
+    expect(params.IMAP.secure).toBeUndefined();
+    expect(params.SMTP.secure).toBeUndefined();
+    expect(params.CALDAV.secure).toBeUndefined();
+  });
+
+  it('maps implicit-TLS SMTP (port 465) and opportunistic IMAP (secure:false) correctly', async () => {
+    const implicitSmtpId = await seedAccount({
+      SMTP: {
+        host: 'smtp.example.com',
+        port: 465,
+        secure: true,
+        password: 'enc:v2:x',
+      },
+    });
+    const plaintextImapId = await seedAccount({
+      IMAP: {
+        host: 'imap.example.com',
+        port: 143,
+        secure: false,
+        password: 'enc:v2:x',
+      },
+    });
+
+    await command.runDataMigration(dataSource);
+
+    expect(
+      (await getConnectionParameters(implicitSmtpId)).SMTP.connectionSecurity,
+    ).toBe('SSL_TLS');
+    expect(
+      (await getConnectionParameters(plaintextImapId)).IMAP.connectionSecurity,
+    ).toBe('STARTTLS');
+  });
+
+  it('is idempotent and leaves already-migrated accounts untouched', async () => {
+    const legacyId = await seedAccount({
+      SMTP: {
+        host: 'smtp.example.com',
+        port: 587,
+        secure: true,
+        password: 'enc:v2:x',
+      },
+    });
+    const alreadyMigratedId = await seedAccount({
+      SMTP: {
+        host: 'smtp.example.com',
+        port: 465,
+        connectionSecurity: 'STARTTLS',
+        password: 'enc:v2:x',
+      },
+    });
+
+    await command.runDataMigration(dataSource);
+    await command.runDataMigration(dataSource);
+
+    expect(
+      (await getConnectionParameters(legacyId)).SMTP.connectionSecurity,
+    ).toBe('STARTTLS');
+    // A pre-set connectionSecurity is never overwritten, even when it disagrees with the port.
+    expect(
+      (await getConnectionParameters(alreadyMigratedId)).SMTP
+        .connectionSecurity,
+    ).toBe('STARTTLS');
+  });
+});