diff --git a/apps/sim/app/workspace/[workspaceId]/home/home.tsx b/apps/sim/app/workspace/[workspaceId]/home/home.tsx
index 8bd266a8724..b3c4cc48519 100644
--- a/apps/sim/app/workspace/[workspaceId]/home/home.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/home/home.tsx
@@ -143,12 +143,21 @@ export function Home({ chatId }: HomeProps = {}) {
     editQueuedMessage,
     previewSession,
     genericResourceData,
+    getCurrentRequestId,
   } = useChat(
     workspaceId,
     chatId,
     getMothershipUseChatOptions({
       onResourceEvent: handleResourceEvent,
       initialActiveResourceId: initialResourceId,
+      onRequestStarted: ({ requestId, userMessageId }) => {
+        captureEvent(posthogRef.current, 'task_request_started', {
+          workspace_id: workspaceId,
+          view: 'mothership',
+          request_id: requestId,
+          user_message_id: userMessageId,
+        })
+      },
     })
   )
 
@@ -198,6 +207,7 @@ export function Home({ chatId }: HomeProps = {}) {
     captureEvent(posthogRef.current, 'task_generation_aborted', {
       workspace_id: workspaceId,
       view: 'mothership',
+      request_id: getCurrentRequestId(),
     })
     void stopGeneration().catch(() => {})
   }
diff --git a/apps/sim/app/workspace/[workspaceId]/home/hooks/use-chat.ts b/apps/sim/app/workspace/[workspaceId]/home/hooks/use-chat.ts
index 6d2c7527a6b..f320d44d46a 100644
--- a/apps/sim/app/workspace/[workspaceId]/home/hooks/use-chat.ts
+++ b/apps/sim/app/workspace/[workspaceId]/home/hooks/use-chat.ts
@@ -167,6 +167,7 @@ export interface UseChatReturn {
   editQueuedMessage: (id: string) => QueuedMessage | undefined
   previewSession: FilePreviewSession | null
   genericResourceData: GenericResourceData | null
+  getCurrentRequestId: () => string | undefined
 }
 
 const DEPLOY_TOOL_NAMES: Set<string> = new Set([
@@ -1278,6 +1279,8 @@ export interface UseChatOptions {
   onTitleUpdate?: () => void
   onStreamEnd?: (chatId: string, messages: ChatMessage[]) => void
   initialActiveResourceId?: string | null
+  /** Fired when the server's `traceparent` response header arrives, before any stream content. */
+  onRequestStarted?: (info: { requestId: string; userMessageId: string }) => void
 }
 
 interface ActiveStreamRecovery {
@@ -1293,7 +1296,10 @@ interface StopGenerationOptions {
 }
 
 export function getMothershipUseChatOptions(
-  options: Pick<UseChatOptions, 'onResourceEvent' | 'onStreamEnd' | 'initialActiveResourceId'> = {}
+  options: Pick<
+    UseChatOptions,
+    'onResourceEvent' | 'onStreamEnd' | 'initialActiveResourceId' | 'onRequestStarted'
+  > = {}
 ): UseChatOptions {
   return {
     apiPath: MOTHERSHIP_CHAT_API_PATH,
@@ -1305,7 +1311,7 @@ export function getMothershipUseChatOptions(
 export function getWorkflowCopilotUseChatOptions(
   options: Pick<
     UseChatOptions,
-    'workflowId' | 'onToolResult' | 'onTitleUpdate' | 'onStreamEnd'
+    'workflowId' | 'onToolResult' | 'onTitleUpdate' | 'onStreamEnd' | 'onRequestStarted'
   > = {}
 ): UseChatOptions {
   return {
@@ -1351,6 +1357,13 @@ export function useChat(
   onTitleUpdateRef.current = options?.onTitleUpdate
   const onStreamEndRef = useRef(options?.onStreamEnd)
   onStreamEndRef.current = options?.onStreamEnd
+  const onRequestStartedRef = useRef(options?.onRequestStarted)
+  onRequestStartedRef.current = options?.onRequestStarted
+
+  const getCurrentRequestId = useCallback(() => {
+    const traceId = streamTraceparentRef.current?.split('-')[1] ?? ''
+    return /^[0-9a-f]{32}$/.test(traceId) ? traceId : undefined
+  }, [])
 
   const clearQueueDispatchState = useCallback(() => {
     queueDispatchEpochRef.current++
@@ -4209,6 +4222,14 @@ export function useChat(
         if (traceparent) {
           streamTraceparentRef.current = traceparent
           setCurrentChatTraceparent(traceparent)
+          const traceId = traceparent.split('-')[1] ?? ''
+          if (/^[0-9a-f]{32}$/.test(traceId)) {
+            try {
+              onRequestStartedRef.current?.({ requestId: traceId, userMessageId })
+            } catch (callbackError) {
+              logger.warn('onRequestStarted callback threw', { error: callbackError })
+            }
+          }
         }
 
         if (!response.ok) {
@@ -5103,5 +5124,6 @@ export function useChat(
     editQueuedMessage,
     previewSession,
     genericResourceData,
+    getCurrentRequestId,
   }
 }
diff --git a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/panel.tsx b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/panel.tsx
index 64acc3d2a27..de69bbd886c 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/panel.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/panel.tsx
@@ -346,6 +346,7 @@ export const Panel = memo(function Panel({ workspaceId: propWorkspaceId }: Panel
     removeFromQueue: copilotRemoveFromQueue,
     sendNow: copilotSendNow,
     editQueuedMessage: copilotEditQueuedMessage,
+    getCurrentRequestId: getCopilotCurrentRequestId,
   } = useChat(
     workspaceId,
     copilotChatId,
@@ -353,6 +354,14 @@ export const Panel = memo(function Panel({ workspaceId: propWorkspaceId }: Panel
       workflowId: activeWorkflowId || undefined,
       onTitleUpdate: loadCopilotChats,
       onToolResult: handleCopilotToolResult,
+      onRequestStarted: ({ requestId, userMessageId }) => {
+        captureEvent(posthogRef.current, 'task_request_started', {
+          workspace_id: workspaceId,
+          view: 'copilot',
+          request_id: requestId,
+          user_message_id: userMessageId,
+        })
+      },
     })
   )
 
@@ -413,9 +422,10 @@ export const Panel = memo(function Panel({ workspaceId: propWorkspaceId }: Panel
     captureEvent(posthogRef.current, 'task_generation_aborted', {
       workspace_id: workspaceId,
       view: 'copilot',
+      request_id: getCopilotCurrentRequestId(),
     })
     copilotStopGeneration()
-  }, [copilotStopGeneration, workspaceId])
+  }, [copilotStopGeneration, getCopilotCurrentRequestId, workspaceId])
 
   const handleCopilotSubmit = useCallback(
     (text: string, fileAttachments?: FileAttachmentForApi[], contexts?: ChatContext[]) => {
diff --git a/apps/sim/lib/posthog/events.ts b/apps/sim/lib/posthog/events.ts
index 41f26124919..7f928d7f70a 100644
--- a/apps/sim/lib/posthog/events.ts
+++ b/apps/sim/lib/posthog/events.ts
@@ -418,6 +418,7 @@ export interface PostHogEventMap {
   task_generation_aborted: {
     workspace_id: string
     view: 'mothership' | 'copilot'
+    request_id?: string
   }
 
   task_message_sent: {
@@ -427,6 +428,14 @@ export interface PostHogEventMap {
     is_new_task: boolean
   }
 
+  /** Pairs with `task_message_sent` via `request_id` for correlation with server-side logs. */
+  task_request_started: {
+    workspace_id: string
+    view: 'mothership' | 'copilot'
+    request_id: string
+    user_message_id: string
+  }
+
   tour_started: {
     tour_type: 'nav' | 'workflow'
   }
diff --git a/apps/sim/lib/posthog/server.ts b/apps/sim/lib/posthog/server.ts
index 99a76a402cc..c81349e2e79 100644
--- a/apps/sim/lib/posthog/server.ts
+++ b/apps/sim/lib/posthog/server.ts
@@ -1,4 +1,4 @@
-import { createLogger } from '@sim/logger'
+import { createLogger, getRequestContext } from '@sim/logger'
 import type { PostHog } from 'posthog-node'
 import type { PostHogEventMap, PostHogEventName } from '@/lib/posthog/events'
 
@@ -71,11 +71,14 @@ export function captureServerEvent<E extends PostHogEventName>(
     const client = getClient()
     if (!client) return
 
+    const contextRequestId = getRequestContext()?.requestId
+    const props = properties as Record<string, unknown>
     client.capture({
       distinctId,
       event,
       properties: {
         ...properties,
+        ...(contextRequestId && !('request_id' in props) ? { request_id: contextRequestId } : {}),
         ...(options?.groups ? { $groups: options.groups } : {}),
         ...(options?.set ? { $set: options.set } : {}),
         ...(options?.setOnce ? { $set_once: options.setOnce } : {}),