diff --git a/packages/twenty-server/src/engine/core-modules/billing/billing.exception.ts b/packages/twenty-server/src/engine/core-modules/billing/billing.exception.ts
index ff8f3ace02..1fa3446f41 100644
--- a/packages/twenty-server/src/engine/core-modules/billing/billing.exception.ts
+++ b/packages/twenty-server/src/engine/core-modules/billing/billing.exception.ts
@@ -4,6 +4,7 @@ import { type MessageDescriptor } from '@lingui/core';
 import { msg } from '@lingui/core/macro';
 import { assertUnreachable } from 'twenty-shared/utils';
 
+import { getBillingExceptionStatusCode } from 'src/engine/core-modules/billing/utils/get-billing-exception-status-code.util';
 import { CustomException } from 'src/utils/custom-exception';
 
 export enum BillingExceptionCode {
@@ -107,5 +108,6 @@ export class BillingException extends CustomException<BillingExceptionCode> {
       userFriendlyMessage:
         userFriendlyMessage ?? getBillingExceptionUserFriendlyMessage(code),
     });
+    this.statusCode = getBillingExceptionStatusCode(this);
   }
 }
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 d74109dff5..c91cfafae3 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
@@ -4,6 +4,7 @@ import {
   convertToModelMessages,
   hasToolCall,
   type LanguageModelUsage,
+  NoOutputGeneratedError,
   stepCountIs,
   type StepResult,
   streamText,
@@ -335,6 +336,7 @@ export class ChatExecutionService {
     let stepStartedAt = streamStartedAt;
     let ttftRecorded = false;
     let stepIndex = 0;
+    let lastUnderlyingStreamError: unknown;
 
     const emitTurnUsageEvent = async (steps: StepResult<ToolSet>[]) => {
       const usage = steps.reduce<LanguageModelUsage>(
@@ -482,6 +484,12 @@ export class ChatExecutionService {
           });
         }
       },
+      onError: ({ error }) => {
+        lastUnderlyingStreamError = error;
+        this.logger.error(
+          `Stream ${streamId} emitted an error: ${error instanceof Error ? error.message : String(error)}`,
+        );
+      },
       experimental_onToolCallFinish: (event) => {
         this.metricsService.recordHistogram({
           key: MetricsKeys.AiChatToolExecutionDurationMs,
@@ -599,6 +607,43 @@ export class ChatExecutionService {
         if (error?.name === 'AbortError') {
           return;
         }
+
+        if (
+          error instanceof AiException &&
+          error.code === AiExceptionCode.STREAM_INTERRUPTED
+        ) {
+          return;
+        }
+
+        if (NoOutputGeneratedError.isInstance(error)) {
+          const underlying = lastUnderlyingStreamError;
+
+          this.exceptionHandlerService.captureExceptions([
+            Object.assign(
+              new Error(
+                `AI chat stream produced no output. ${JSON.stringify({
+                  modelId: registeredModel.modelId,
+                  provider: registeredModel.sdkPackage,
+                  workspaceId: workspace.id,
+                  threadId,
+                  streamId,
+                  turnId,
+                  messageCount: messages.length,
+                  conversationSizeTokens,
+                  elapsedMs: Math.round(performance.now() - streamStartedAt),
+                  underlyingError:
+                    underlying instanceof Error
+                      ? `${underlying.name}: ${underlying.message}`
+                      : String(underlying ?? 'none-recorded'),
+                })}`,
+              ),
+              { cause: underlying },
+            ),
+          ]);
+
+          return;
+        }
+
         this.exceptionHandlerService.captureExceptions([error]);
       });
 
diff --git a/packages/twenty-server/src/engine/utils/global-exception-handler.util.ts b/packages/twenty-server/src/engine/utils/global-exception-handler.util.ts
index 3e7507a3e9..1154d159f3 100644
--- a/packages/twenty-server/src/engine/utils/global-exception-handler.util.ts
+++ b/packages/twenty-server/src/engine/utils/global-exception-handler.util.ts
@@ -18,7 +18,8 @@ import {
   TimeoutError,
   ValidationError,
 } from 'src/engine/core-modules/graphql/utils/graphql-errors.util';
-import { type CustomException } from 'src/utils/custom-exception';
+import { CustomException } from 'src/utils/custom-exception';
+import { isDefined } from 'twenty-shared/utils';
 
 const graphQLPredefinedExceptions = {
   400: ValidationError,
@@ -62,6 +63,14 @@ export const shouldCaptureException = (
   exception: Error,
   statusCode?: number,
 ): boolean => {
+  if (
+    exception instanceof CustomException &&
+    isDefined(exception.statusCode) &&
+    exception.statusCode < 500
+  ) {
+    return false;
+  }
+
   if (
     exception instanceof GraphQLError &&
     (exception?.extensions?.http?.status ?? 500) < 500
diff --git a/packages/twenty-server/src/utils/custom-exception.ts b/packages/twenty-server/src/utils/custom-exception.ts
index 321dd5b7f8..db473a57e1 100644
--- a/packages/twenty-server/src/utils/custom-exception.ts
+++ b/packages/twenty-server/src/utils/custom-exception.ts
@@ -22,11 +22,14 @@ export abstract class CustomException<
 > extends CustomError {
   code: ExceptionCode;
   userFriendlyMessage: MessageDescriptor;
+  statusCode?: number;
 
   constructor(
     message: ExceptionMessage,
     code: ExceptionCode,
-    { userFriendlyMessage }: { userFriendlyMessage: MessageDescriptor },
+    {
+      userFriendlyMessage,
+    }: { userFriendlyMessage: MessageDescriptor; statusCode?: number },
   ) {
     super(message);
     this.code = code;