diff --git a/apps/trigger/src/tasks/analyst-agent-task/analyst-agent-task.ts b/apps/trigger/src/tasks/analyst-agent-task/analyst-agent-task.ts
index f74bdc6aa..54ef0f077 100644
--- a/apps/trigger/src/tasks/analyst-agent-task/analyst-agent-task.ts
+++ b/apps/trigger/src/tasks/analyst-agent-task/analyst-agent-task.ts
@@ -1,3 +1,4 @@
+import { randomUUID } from 'node:crypto';
 import { logger, schemaTask, tasks } from '@trigger.dev/sdk';
 import { currentSpan, initLogger, wrapTraced } from 'braintrust';
 import { analystQueue } from '../../queues/analyst-queue';
@@ -12,6 +13,8 @@ import {
   getOrganizationDataSource,
   getOrganizationDocs,
   getUserPersonalization,
+  updateMessage,
+  updateMessageEntries,
 } from '@buster/database/queries';
 
 // Access control imports
@@ -134,11 +137,11 @@ class ResourceTracker {
       },
       cpuUsage: finalCpuUsage
         ? {
-            userTimeMs: Math.round(finalCpuUsage.user / 1000),
-            systemTimeMs: Math.round(finalCpuUsage.system / 1000),
-            totalTimeMs: Math.round(totalCpuTime / 1000),
-            estimatedUsagePercent: Math.round(cpuPercentage * 100) / 100,
-          }
+          userTimeMs: Math.round(finalCpuUsage.user / 1000),
+          systemTimeMs: Math.round(finalCpuUsage.system / 1000),
+          totalTimeMs: Math.round(totalCpuTime / 1000),
+          estimatedUsagePercent: Math.round(cpuPercentage * 100) / 100,
+        }
         : { error: 'CPU usage not available' },
       stageBreakdown: this.snapshots.map((snapshot, index) => {
         const prevSnapshot = index > 0 ? this.snapshots[index - 1] : null;
@@ -249,6 +252,51 @@ export const analystAgentTask: ReturnType<
   schema: AnalystAgentTaskInputSchema,
   queue: analystQueue,
   maxDuration: 1200, // 20 minutes for complex analysis
+  retry: {
+    maxAttempts: 0
+  },
+  onFailure: async ({ error, payload }) => {
+    // Log the failure for debugging
+    logger.error('Analyst agent task failed - executing onFailure handler', {
+      messageId: payload.message_id,
+      error: error instanceof Error ? error.message : 'Unknown error',
+      errorType: error instanceof Error ? error.name : typeof error,
+    });
+
+    try {
+      // Add error message to user and mark as complete
+      const errorResponseId = randomUUID();
+
+      // Add the error response message
+      await updateMessageEntries({
+        messageId: payload.message_id,
+        responseMessages: [
+          {
+            id: errorResponseId,
+            type: 'text',
+            message: "I'm sorry, I ran into a technical error. Please try your request again.",
+          },
+        ],
+      });
+
+      // Mark the message as complete with final reasoning
+      await updateMessage(payload.message_id, {
+        isCompleted: true,
+        finalReasoningMessage: 'Finished reasoning.',
+      });
+
+      logger.log('Error response added and message marked complete', {
+        messageId: payload.message_id,
+        errorResponseId,
+      });
+    } catch (handlerError) {
+      // Log but don't throw - onFailure should never throw
+      logger.error('Failed to update message in onFailure handler', {
+        messageId: payload.message_id,
+        error: handlerError instanceof Error ? handlerError.message : 'Unknown error',
+      });
+    }
+  },
   run: async (payload): Promise<AnalystAgentTaskOutput> => {
     const taskStartTime = Date.now();
     const resourceTracker = new ResourceTracker();
@@ -376,12 +424,12 @@ export const analystAgentTask: ReturnType<
         conversationHistory.length > 0
           ? conversationHistory
           : [
-              {
-                role: 'user',
-                // v5 supports string content directly for user messages
-                content: messageContext.requestMessage,
-              },
-            ];
+            {
+              role: 'user',
+              // v5 supports string content directly for user messages
+              content: messageContext.requestMessage,
+            },
+          ];
 
       const workflowInput: AnalystWorkflowInput = {
         messages: modelMessages,
@@ -435,7 +483,28 @@ export const analystAgentTask: ReturnType<
         }
       );
 
-      await tracedWorkflow();
+      // Wrap workflow execution to capture and log errors before re-throwing
+      try {
+        await tracedWorkflow();
+      } catch (workflowError) {
+        // Log workflow-specific error details
+        logger.error('Analyst workflow execution failed', {
+          messageId: payload.message_id,
+          error: workflowError instanceof Error ? workflowError.message : 'Unknown error',
+          errorType: workflowError instanceof Error ? workflowError.name : typeof workflowError,
+          stack: workflowError instanceof Error ? workflowError.stack : undefined,
+          workflowInput: {
+            messageCount: workflowInput.messages.length,
+            datasetsCount: datasets.length,
+            hasAnalystInstructions: !!analystInstructions,
+            organizationDocsCount: organizationDocs.length,
+          },
+        });
+
+        // Re-throw to let Trigger handle the retry
+        throw workflowError;
+      }
+
       const totalWorkflowTime = Date.now() - workflowExecutionStart;
 
       logger.log('Analyst workflow completed successfully', {
@@ -509,27 +578,20 @@ export const analystAgentTask: ReturnType<
       logPerformanceMetrics('task-error', payload.message_id, taskStartTime, resourceTracker);
       resourceTracker.generateReport(payload.message_id);
 
-      logger.error('Task execution failed', {
+      logger.error('Task execution failed - will retry', {
         messageId: payload.message_id,
         error: errorMessage,
+        errorType: error instanceof Error ? error.name : typeof error,
+        stack: error instanceof Error ? error.stack : undefined,
         executionTimeMs: totalExecutionTime,
+        errorCode: getErrorCode(error),
       });
 
       // Need to flush the Braintrust logger to ensure all traces are sent
       await braintrustLogger.flush();
 
-      return {
-        success: false,
-        messageId: payload.message_id,
-        error: {
-          code: getErrorCode(error),
-          message: errorMessage,
-          details: {
-            operation: 'analyst_agent_task_execution',
-            messageId: payload.message_id,
-          },
-        },
-      };
+      // Re-throw the error so Trigger knows the task failed and should retry
+      throw error;
     }
   },
 });