diff --git a/packages/twenty-front/src/modules/ai/components/AiChatErrorRenderer.tsx b/packages/twenty-front/src/modules/ai/components/AiChatErrorRenderer.tsx
index b4f6e7af1a..a8217903d1 100644
--- a/packages/twenty-front/src/modules/ai/components/AiChatErrorRenderer.tsx
+++ b/packages/twenty-front/src/modules/ai/components/AiChatErrorRenderer.tsx
@@ -22,6 +22,10 @@ export const AiChatErrorRenderer = ({
     return <AiChatApiKeyNotConfiguredMessage />;
   }
 
+  if (isGraphqlErrorOfType(error, AiChatErrorCode.CONTEXT_WINDOW_EXCEEDED)) {
+    return <AiChatErrorMessage error={error} />;
+  }
+
   if (isGraphqlErrorOfType(error, AiChatErrorCode.CONNECTION_LOST)) {
     return <AiChatErrorMessage error={error} />;
   }
diff --git a/packages/twenty-front/src/modules/ai/utils/aiChatErrorCode.ts b/packages/twenty-front/src/modules/ai/utils/aiChatErrorCode.ts
index b106c8c978..bb534f76de 100644
--- a/packages/twenty-front/src/modules/ai/utils/aiChatErrorCode.ts
+++ b/packages/twenty-front/src/modules/ai/utils/aiChatErrorCode.ts
@@ -1,5 +1,6 @@
 export const AiChatErrorCode = {
   BILLING_CREDITS_EXHAUSTED: 'BILLING_CREDITS_EXHAUSTED',
+  CONTEXT_WINDOW_EXCEEDED: 'CONTEXT_WINDOW_EXCEEDED',
   API_KEY_NOT_CONFIGURED: 'API_KEY_NOT_CONFIGURED',
   CONNECTION_LOST: 'CONNECTION_LOST',
 } as const;
diff --git a/packages/twenty-server/src/engine/metadata-modules/ai/ai-chat/services/chat-execution.service.ts b/packages/twenty-server/src/engine/metadata-modules/ai/ai-chat/services/chat-execution.service.ts
index 816cac8602..90799abe8c 100644
--- a/packages/twenty-server/src/engine/metadata-modules/ai/ai-chat/services/chat-execution.service.ts
+++ b/packages/twenty-server/src/engine/metadata-modules/ai/ai-chat/services/chat-execution.service.ts
@@ -41,6 +41,10 @@ import { getToolMetricName } from 'src/engine/core-modules/tool-provider/utils/g
 import { isToolOutputSuccessful } from 'src/engine/core-modules/tool-provider/utils/is-tool-output-successful.util';
 import { resolveToolName } from 'src/engine/core-modules/tool-provider/utils/resolve-tool-name.util';
 import { type WorkspaceEntity } from 'src/engine/core-modules/workspace/workspace.entity';
+import {
+  AiException,
+  AiExceptionCode,
+} from 'src/engine/metadata-modules/ai/ai.exception';
 import { AgentActorContextService } from 'src/engine/metadata-modules/ai/ai-agent-execution/services/agent-actor-context.service';
 import { finalizeDanglingToolParts } from 'src/engine/metadata-modules/ai/ai-agent-execution/utils/finalize-dangling-tool-parts.util';
 import { AGENT_CONFIG } from 'src/engine/metadata-modules/ai/ai-agent/constants/agent-config.const';
@@ -302,8 +306,9 @@ export class ChatExecutionService {
       );
 
     if (pruningResult.isStillOverLimit) {
-      throw new Error(
+      throw new AiException(
         'This conversation is too long for the model to process. Please start a new thread.',
+        AiExceptionCode.CONTEXT_WINDOW_EXCEEDED,
       );
     }
 
diff --git a/packages/twenty-server/src/engine/metadata-modules/ai/ai.exception.ts b/packages/twenty-server/src/engine/metadata-modules/ai/ai.exception.ts
index 919d8e7650..36a7d4b1d2 100644
--- a/packages/twenty-server/src/engine/metadata-modules/ai/ai.exception.ts
+++ b/packages/twenty-server/src/engine/metadata-modules/ai/ai.exception.ts
@@ -12,6 +12,7 @@ export enum AiExceptionCode {
   INVALID_AGENT_INPUT = 'INVALID_AGENT_INPUT',
   THREAD_NOT_FOUND = 'THREAD_NOT_FOUND',
   WORKSPACE_NOT_FOUND = 'WORKSPACE_NOT_FOUND',
+  CONTEXT_WINDOW_EXCEEDED = 'CONTEXT_WINDOW_EXCEEDED',
   INVALID_CHAT_THREAD_TITLE = 'INVALID_CHAT_THREAD_TITLE',
   MESSAGE_NOT_FOUND = 'MESSAGE_NOT_FOUND',
   QUESTION_NOT_PENDING = 'QUESTION_NOT_PENDING',
@@ -39,6 +40,8 @@ const getAiExceptionUserFriendlyMessage = (code: AiExceptionCode) => {
       return msg`Chat thread not found.`;
     case AiExceptionCode.WORKSPACE_NOT_FOUND:
       return msg`Workspace not found.`;
+    case AiExceptionCode.CONTEXT_WINDOW_EXCEEDED:
+      return msg`This conversation is too long for the model. Start a new thread to continue.`;
     case AiExceptionCode.INVALID_CHAT_THREAD_TITLE:
       return msg`Chat thread title cannot be empty.`;
     case AiExceptionCode.MESSAGE_NOT_FOUND:
diff --git a/packages/twenty-server/src/engine/metadata-modules/ai/utils/ai-graphql-api-exception-handler.util.ts b/packages/twenty-server/src/engine/metadata-modules/ai/utils/ai-graphql-api-exception-handler.util.ts
index 5b394de6c1..b54dff9c84 100644
--- a/packages/twenty-server/src/engine/metadata-modules/ai/utils/ai-graphql-api-exception-handler.util.ts
+++ b/packages/twenty-server/src/engine/metadata-modules/ai/utils/ai-graphql-api-exception-handler.util.ts
@@ -27,6 +27,7 @@ export const aiGraphqlApiExceptionHandler = (error: Error) => {
       case AiExceptionCode.MESSAGE_NOT_FOUND:
       case AiExceptionCode.ROLE_NOT_FOUND:
         throw new NotFoundError(error);
+      case AiExceptionCode.CONTEXT_WINDOW_EXCEEDED:
       case AiExceptionCode.INVALID_AGENT_INPUT:
       case AiExceptionCode.INVALID_CHAT_THREAD_TITLE:
       case AiExceptionCode.QUESTION_NOT_PENDING: