diff --git a/frontend/src/lib/components/copilot/chat/AIChatManager.svelte.ts b/frontend/src/lib/components/copilot/chat/AIChatManager.svelte.ts
index 30802b446c..ebc925588b 100644
--- a/frontend/src/lib/components/copilot/chat/AIChatManager.svelte.ts
+++ b/frontend/src/lib/components/copilot/chat/AIChatManager.svelte.ts
@@ -1312,7 +1312,7 @@ export class AIChatManager {
 			if (message.role === 'tool' && message.tool_call_id === toolId && message.userQuestion) {
 				return {
 					...message,
-					content: `User answered question: ${answerSummary}`,
+					content: `Asked: ${message.userQuestion.question} — ${answerSummary}`,
 					isLoading: false,
 					userQuestion: {
 						...message.userQuestion,
@@ -2996,7 +2996,11 @@ export class AIChatManager {
 				return {
 					...message,
 					isLoading: false,
-					content: messageText,
+					// A question's card disappears once canceled, so keep the question
+					// itself readable in the collapsed header.
+					content: message.userQuestion
+						? `Asked: ${message.userQuestion.question} — ${messageText}`
+						: messageText,
 					error: messageText,
 					userQuestion: message.userQuestion
 						? { ...message.userQuestion, canceled: true }
diff --git a/frontend/src/lib/components/copilot/chat/anthropic.ts b/frontend/src/lib/components/copilot/chat/anthropic.ts
index b6e7e57a17..2c19a611a0 100644
--- a/frontend/src/lib/components/copilot/chat/anthropic.ts
+++ b/frontend/src/lib/components/copilot/chat/anthropic.ts
@@ -143,7 +143,7 @@ export async function parseAnthropicCompletion(
 
 				callbacks.setToolStatus(toolId, {
 					isLoading: true,
-					content: `Calling ${toolName}...`,
+					content: tool?.streamingLabel ?? `Calling ${toolName}...`,
 					toolName,
 					isStreamingArguments: shouldStream,
 					showFade: tool?.showFade,
diff --git a/frontend/src/lib/components/copilot/chat/global/core.test.ts b/frontend/src/lib/components/copilot/chat/global/core.test.ts
index 849f462701..407870433d 100644
--- a/frontend/src/lib/components/copilot/chat/global/core.test.ts
+++ b/frontend/src/lib/components/copilot/chat/global/core.test.ts
@@ -3250,7 +3250,7 @@ describe('global AI tools', () => {
 		expect(callbacks.setToolStatus).toHaveBeenLastCalledWith(
 			'test-askUserQuestion',
 			expect.objectContaining({
-				content: 'User answered question: python3',
+				content: 'Asked: Which script language should be used? — python3',
 				isLoading: false,
 				result: 'python3',
 				userQuestion: expect.objectContaining({ selectedChoices: ['python3'] })
@@ -3288,7 +3288,7 @@ describe('global AI tools', () => {
 		expect(callbacks.setToolStatus).toHaveBeenLastCalledWith(
 			'test-askUserQuestion',
 			expect.objectContaining({
-				content: 'User answered question: bun, go',
+				content: 'Asked: Which languages should be supported? — bun, go',
 				isLoading: false,
 				result: '- bun\n- go',
 				userQuestion: expect.objectContaining({ selectedChoices: ['bun', 'go'] })
@@ -3362,7 +3362,7 @@ describe('global AI tools', () => {
 		expect(callbacks.setToolStatus).toHaveBeenLastCalledWith(
 			'test-askUserQuestion',
 			expect.objectContaining({
-				content: 'User answered question: use deno instead',
+				content: 'Asked: Which script language should be used? — use deno instead',
 				result: 'use deno instead',
 				userQuestion: expect.objectContaining({ selectedChoices: ['use deno instead'] })
 			})
diff --git a/frontend/src/lib/components/copilot/chat/global/core.ts b/frontend/src/lib/components/copilot/chat/global/core.ts
index 3254f555f8..f9ba044f0a 100644
--- a/frontend/src/lib/components/copilot/chat/global/core.ts
+++ b/frontend/src/lib/components/copilot/chat/global/core.ts
@@ -2133,6 +2133,7 @@ export const globalTools: Tool<{}>[] = [
 			'askUserQuestion',
 			'Ask the user a question with proposed answers and wait for their selected or custom answer before continuing.'
 		),
+		streamingLabel: 'Asking the user a question...',
 		fn: async ({ args, toolId, toolCallbacks }) => {
 			const parsed = askUserQuestionSchema.parse(args)
 			const userQuestion = {
@@ -2142,7 +2143,7 @@ export const globalTools: Tool<{}>[] = [
 			}
 
 			toolCallbacks.setToolStatus(toolId, {
-				content: parsed.question,
+				content: `Asking user: ${parsed.question}`,
 				userQuestion,
 				isLoading: true
 			})
@@ -2162,7 +2163,7 @@ export const globalTools: Tool<{}>[] = [
 			if (!selected?.length) {
 				const message = 'Question cancelled by user'
 				toolCallbacks.setToolStatus(toolId, {
-					content: message,
+					content: `Asked: ${parsed.question} — cancelled by user`,
 					userQuestion: { ...userQuestion, canceled: true },
 					isLoading: false,
 					error: message
@@ -2176,12 +2177,13 @@ export const globalTools: Tool<{}>[] = [
 			// ("Yes, immediately") stays unambiguous to the model reading it back.
 			const answerText =
 				selected.length === 1 ? selected[0] : selected.map((c) => `- ${c}`).join('\n')
-			// The collapsed tool-header is a human glance, not model input, so the picks
-			// read as a compact comma list there instead of a stacked bullet list.
+			// The collapsed tool-header is a human glance, not model input, so it carries
+			// the question plus the picks as a compact comma list (not a bullet list) —
+			// it is the only place the exchange stays readable in the transcript.
 			const answerSummary = selected.join(', ')
 
 			toolCallbacks.setToolStatus(toolId, {
-				content: `User answered question: ${answerSummary}`,
+				content: `Asked: ${parsed.question} — ${answerSummary}`,
 				userQuestion: {
 					...userQuestion,
 					selectedChoices: selected
diff --git a/frontend/src/lib/components/copilot/chat/openai-responses.ts b/frontend/src/lib/components/copilot/chat/openai-responses.ts
index f66d50bb09..3a83595f8f 100644
--- a/frontend/src/lib/components/copilot/chat/openai-responses.ts
+++ b/frontend/src/lib/components/copilot/chat/openai-responses.ts
@@ -337,7 +337,7 @@ export async function parseOpenAIResponsesCompletion(
 			callbacks.onMessageEnd()
 			callbacks.setToolStatus(`${item.id}`, {
 				isLoading: true,
-				content: `Calling ${item.name}...`,
+				content: tool?.streamingLabel ?? `Calling ${item.name}...`,
 				toolName: item.name,
 				isStreamingArguments: shouldStream,
 				showFade: tool?.showFade,
diff --git a/frontend/src/lib/components/copilot/chat/shared.ts b/frontend/src/lib/components/copilot/chat/shared.ts
index 60b85e16de..02f92519b7 100644
--- a/frontend/src/lib/components/copilot/chat/shared.ts
+++ b/frontend/src/lib/components/copilot/chat/shared.ts
@@ -820,6 +820,9 @@ export interface Tool<T> {
 	autoCollapseDetails?: boolean
 	streamArguments?: boolean
 	showFade?: boolean
+	/** Header shown while the model is still streaming this call's arguments,
+	 * before `fn` runs and sets a real status. Defaults to "Calling <name>...". */
+	streamingLabel?: string
 }
 
 /** Status of a job the chat started and tracks in the jobs tray. Mirrors the
diff --git a/frontend/src/lib/components/copilot/lib.ts b/frontend/src/lib/components/copilot/lib.ts
index 88afa58b7d..2b261a21e0 100644
--- a/frontend/src/lib/components/copilot/lib.ts
+++ b/frontend/src/lib/components/copilot/lib.ts
@@ -1176,7 +1176,7 @@ export async function parseOpenAICompletion(
 					// Display tool call with streaming parameters if enabled
 					callbacks.setToolStatus(toolCallId, {
 						isLoading: true,
-						content: `Calling ${funcName}...`,
+						content: tool?.streamingLabel ?? `Calling ${funcName}...`,
 						toolName: funcName,
 						isStreamingArguments: shouldStream,
 						showFade: tool?.showFade,