diff --git a/apps/studio/src/components/studio-code-session/conversation/index.test.tsx b/apps/studio/src/components/studio-code-session/conversation/index.test.tsx
new file mode 100644
index 0000000000..6c6b56cd4a
--- /dev/null
+++ b/apps/studio/src/components/studio-code-session/conversation/index.test.tsx
@@ -0,0 +1,62 @@
+/**
+ * @jest-environment node
+ */
+import { describe, expect, it } from 'vitest';
+import { entriesToRenderItems } from './index';
+import type { SessionEntry } from '@earendil-works/pi-coding-agent';
+
+function customEntry( customType: string, data: unknown ): SessionEntry {
+	return {
+		type: 'custom',
+		id: Math.random().toString( 36 ).slice( 2 ),
+		parentId: null,
+		timestamp: '2026-06-19T00:00:00.000Z',
+		customType,
+		data,
+	} as unknown as SessionEntry;
+}
+
+function question( q: string, options: string[] ): SessionEntry {
+	return customEntry( 'studio.agent_question', {
+		question: q,
+		options: options.map( ( label ) => ( { label, description: '' } ) ),
+	} );
+}
+
+function answer( text: string ): SessionEntry {
+	return customEntry( 'studio.user_prompt', { text, source: 'ask_user' } );
+}
+
+describe( 'entriesToRenderItems – persisted picked answers', () => {
+	it( 'pairs a question with its persisted ask_user answer', () => {
+		const items = entriesToRenderItems( [ question( 'Pick one', [ 'A', 'B' ] ), answer( 'B' ) ] );
+		const q = items.find( ( i ) => i.kind === 'agent-question' );
+		expect( q ).toMatchObject( { kind: 'agent-question', question: 'Pick one', answer: 'B' } );
+	} );
+
+	it( 'pairs a batch of questions with answers by order', () => {
+		// The CLI persists all questions first, then all answers, in question order.
+		const items = entriesToRenderItems( [
+			question( 'Q1', [ 'A', 'B' ] ),
+			question( 'Q2', [ 'C', 'D' ] ),
+			answer( 'A' ),
+			answer( 'D' ),
+		] );
+		const questions = items.filter( ( i ) => i.kind === 'agent-question' );
+		expect( questions ).toMatchObject( [
+			{ question: 'Q1', answer: 'A' },
+			{ question: 'Q2', answer: 'D' },
+		] );
+	} );
+
+	it( 'leaves answer undefined for an unanswered question', () => {
+		const items = entriesToRenderItems( [ question( 'Q1', [ 'A', 'B' ] ) ] );
+		const q = items.find( ( i ) => i.kind === 'agent-question' );
+		expect( q ).toMatchObject( { question: 'Q1', answer: undefined } );
+	} );
+
+	it( 'does not render ask_user prompts as user text', () => {
+		const items = entriesToRenderItems( [ question( 'Q1', [ 'A' ] ), answer( 'A' ) ] );
+		expect( items.some( ( i ) => i.kind === 'user-text' ) ).toBe( false );
+	} );
+} );
diff --git a/apps/studio/src/components/studio-code-session/conversation/index.tsx b/apps/studio/src/components/studio-code-session/conversation/index.tsx
index e32e8f6abd..bbdc8bbb81 100644
--- a/apps/studio/src/components/studio-code-session/conversation/index.tsx
+++ b/apps/studio/src/components/studio-code-session/conversation/index.tsx
@@ -39,6 +39,7 @@ type RenderItem =
 			key: string;
 			question: string;
 			options: Array< { label: string; description: string } >;
+			answer?: string;
 	  }
 	| { kind: 'interrupted-marker'; key: string };
 
@@ -64,7 +65,7 @@ interface PiToolResultLike {
 
 const HIDDEN_TOOL_ROWS = new Set( [ 'studio_present' ] );
 
-function entriesToRenderItems( entries: SessionEntry[] ): RenderItem[] {
+export function entriesToRenderItems( entries: SessionEntry[] ): RenderItem[] {
 	// First pass: collect tool_call_id → tool_result pairings so each
 	// `toolCall` row can render its output inline.
 	const resultsByToolCallId = new Map< string, NormalizedToolResult >();
@@ -82,6 +83,27 @@ function entriesToRenderItems( entries: SessionEntry[] ): RenderItem[] {
 		} );
 	}
 
+	// Answers picked for `studio.agent_question` entries are persisted as
+	// `studio.user_prompt` entries with `source: 'ask_user'` (the CLI writes all
+	// questions in a batch first, then all answers, in question order). They are
+	// not rendered as prompts, but we reuse them to keep the picked option
+	// highlighted in history after the turn moves on — and after a reload, since
+	// this is disk-backed (unlike the ephemeral `pendingAnswers` state).
+	const askUserAnswers: string[] = [];
+	for ( const entry of entries ) {
+		if ( isStudioCustomEntryOfType( entry, 'studio.user_prompt' ) ) {
+			const data = ( entry as StudioCustomEntry< 'studio.user_prompt' > ).data;
+			if ( data?.source === 'ask_user' ) {
+				askUserAnswers.push( data.text );
+			}
+		}
+	}
+	// ponytail: ordinal pairing — i-th question ↔ i-th ask_user answer. A skipped
+	// question (empty answer isn't persisted) would shift later pairings, but such
+	// batches are interrupted and become non-interactive. Upgrade to label-matching
+	// only if that case ever shows wrong highlights.
+	let questionOrdinal = 0;
+
 	const items: RenderItem[] = [];
 	entries.forEach( ( entry, entryIndex ) => {
 		if ( isStudioCustomEntryOfType( entry, 'studio.user_prompt' ) ) {
@@ -139,7 +161,9 @@ function entriesToRenderItems( entries: SessionEntry[] ): RenderItem[] {
 				key: `${ entryIndex }:question`,
 				question: data.question,
 				options: data.options,
+				answer: askUserAnswers[ questionOrdinal ],
 			} );
+			questionOrdinal += 1;
 			return;
 		}
 
@@ -317,6 +341,7 @@ export function Conversation( {
 	startedAt,
 	pendingQuestions,
 	pendingAnswers,
+	answeredQuestions,
 	onAnswerQuestion,
 }: {
 	data: LoadedAiSession;
@@ -324,6 +349,7 @@ export function Conversation( {
 	startedAt: number | null;
 	pendingQuestions: Set< string >;
 	pendingAnswers: Record< string, string >;
+	answeredQuestions: Record< string, string >;
 	onAnswerQuestion: ( question: string, label: string ) => void;
 } ) {
 	const entries = data.entries;
@@ -359,7 +385,11 @@ export function Conversation( {
 								question={ item.question }
 								options={ item.options }
 								isInteractive={ pendingQuestions.has( item.question ) }
-								pickedLabel={ pendingAnswers[ item.question ] }
+								pickedLabel={
+									pendingAnswers[ item.question ] ??
+									answeredQuestions[ item.question ] ??
+									item.answer
+								}
 								onAnswer={ ( label ) => onAnswerQuestion( item.question, label ) }
 							/>
 						);
diff --git a/apps/studio/src/components/studio-code-session/conversation/style.module.css b/apps/studio/src/components/studio-code-session/conversation/style.module.css
index 5c88fb917f..5ab27f9bfc 100644
--- a/apps/studio/src/components/studio-code-session/conversation/style.module.css
+++ b/apps/studio/src/components/studio-code-session/conversation/style.module.css
@@ -178,17 +178,24 @@
 }
 
 .questionOption {
-	background: none;
-	border: none;
-	padding: 0;
-	color: var(--color-frame-theme);
+	display: inline-flex;
+	align-items: center;
+	background-color: var(--color-frame-surface);
+	border: 1px solid var(--color-frame-border);
+	border-radius: 6px;
+	padding: 4px 10px;
+	color: var(--color-frame-text);
 	font: inherit;
+	font-size: var(--wpds-typography-font-size-sm);
+	line-height: 1.4;
 	cursor: pointer;
+	transition: background-color 120ms ease, border-color 120ms ease;
 }
 
 .questionOption:hover:not(:disabled),
 .questionOption:focus-visible:not(:disabled) {
-	text-decoration: underline;
+	background-color: var(--color-frame-surface-alt);
+	border-color: var(--color-frame-text-secondary);
 }
 
 .questionOption:disabled {
@@ -202,10 +209,19 @@
 .questionOptionPicked,
 .questionOptionPicked:disabled {
 	font-weight: 600;
-	color: var(--color-frame-theme);
+	background-color: var(--color-frame-surface-alt);
+	border-color: var(--color-frame-theme);
+	color: var(--color-frame-text);
 	opacity: 1;
 }
 
+/* Once finalized, the picked option still reads as the selection (accent
+   border) but dims so it clearly looks disabled rather than clickable. */
+.questionOptionPicked:disabled {
+	opacity: 0.6;
+	cursor: default;
+}
+
 .interruptedMarker {
 	align-self: center;
 	margin: var(--wpds-dimension-padding-sm) 0;
diff --git a/apps/studio/src/components/studio-code-session/index.tsx b/apps/studio/src/components/studio-code-session/index.tsx
index 4adcf58eb4..24d226cdf6 100644
--- a/apps/studio/src/components/studio-code-session/index.tsx
+++ b/apps/studio/src/components/studio-code-session/index.tsx
@@ -253,6 +253,7 @@ function SessionContent( { selectedSite }: { selectedSite: SiteDetails } ) {
 		error: runError,
 		pendingQuestions,
 		pendingAnswers,
+		answeredQuestions,
 		queuedPrompts,
 		sendMessage,
 		interrupt,
@@ -418,6 +419,7 @@ function SessionContent( { selectedSite }: { selectedSite: SiteDetails } ) {
 							startedAt={ startedAt }
 							pendingQuestions={ pendingQuestionTexts }
 							pendingAnswers={ pendingAnswers }
+							answeredQuestions={ answeredQuestions }
 							onAnswerQuestion={ answerQuestion }
 						/>
 					) }
diff --git a/apps/studio/src/components/studio-code-session/use-agent-run.tsx b/apps/studio/src/components/studio-code-session/use-agent-run.tsx
index f1f14cf12b..e73520a19b 100644
--- a/apps/studio/src/components/studio-code-session/use-agent-run.tsx
+++ b/apps/studio/src/components/studio-code-session/use-agent-run.tsx
@@ -69,6 +69,12 @@ export interface LiveAgentEvents {
 	// The user can re-click an option to change their pick until every
 	// question is answered, at which point the batch is dispatched.
 	pendingAnswers: Record< string, string >;
+	// Answers that have already been dispatched, kept for the lifetime of the
+	// session so the picked option stays highlighted in history. The persisted
+	// `ask_user` entry only reaches the transcript after a disk refetch (which
+	// lags the live run), so this in-memory map bridges that gap; on reload the
+	// transcript falls back to the disk-backed answer.
+	answeredQuestions: Record< string, string >;
 	// Follow-up prompts the user staged while a turn was in flight. FIFO:
 	// the head auto-dispatches when the current run ends.
 	queuedPrompts: QueuedPrompt[];
@@ -92,6 +98,7 @@ interface State {
 	isInterrupting: boolean;
 	pendingQuestions: PendingQuestion[];
 	pendingAnswers: Record< string, string >;
+	answeredQuestions: Record< string, string >;
 	queuedPrompts: QueuedPrompt[];
 }
 
@@ -103,6 +110,7 @@ const initialState: State = {
 	isInterrupting: false,
 	pendingQuestions: [],
 	pendingAnswers: {},
+	answeredQuestions: {},
 	queuedPrompts: [],
 };
 
@@ -116,7 +124,7 @@ type Action =
 	| { type: 'interrupt_requested' }
 	| { type: 'questions_added'; questions: PendingQuestion[] }
 	| { type: 'question_answered'; question: string; answer: string }
-	| { type: 'batch_dispatched' }
+	| { type: 'batch_dispatched'; answers: Record< string, string > }
 	| { type: 'queue_append'; prompt: QueuedPrompt }
 	| { type: 'queue_remove'; id: string }
 	| { type: 'queue_shift' }
@@ -162,8 +170,13 @@ function reducer( state: State, action: Action ): State {
 			};
 		case 'run_ended':
 			// Preserve the queue across run boundaries so staged follow-ups
-			// survive the transition. Everything else resets.
-			return { ...initialState, queuedPrompts: state.queuedPrompts };
+			// survive the transition, and the answered-question map so picked
+			// options stay highlighted in history. Everything else resets.
+			return {
+				...initialState,
+				queuedPrompts: state.queuedPrompts,
+				answeredQuestions: state.answeredQuestions,
+			};
 		case 'interrupt_requested':
 			return {
 				...state,
@@ -180,12 +193,19 @@ function reducer( state: State, action: Action ): State {
 				pendingQuestions: [ ...state.pendingQuestions, ...action.questions ],
 			};
 		case 'question_answered':
+			// `answeredQuestions` is only written on dispatch; mid-batch the live
+			// highlight comes from `pendingAnswers`.
 			return {
 				...state,
 				pendingAnswers: { ...state.pendingAnswers, [ action.question ]: action.answer },
 			};
 		case 'batch_dispatched':
-			return { ...state, pendingQuestions: [], pendingAnswers: {} };
+			return {
+				...state,
+				pendingQuestions: [],
+				pendingAnswers: {},
+				answeredQuestions: { ...state.answeredQuestions, ...action.answers },
+			};
 		case 'queue_append':
 			return { ...state, queuedPrompts: [ ...state.queuedPrompts, action.prompt ] };
 		case 'queue_remove':
@@ -561,7 +581,7 @@ export function AgentRunProvider( { children }: PropsWithChildren ) {
 				( q ) => typeof nextAnswers[ q.question ] === 'string'
 			);
 			if ( complete ) {
-				dispatchSession( sessionId, { type: 'batch_dispatched' } );
+				dispatchSession( sessionId, { type: 'batch_dispatched', answers: nextAnswers } );
 				void getIpcApi().answerAiAgentQuestion( state.runId, nextAnswers );
 			} else {
 				dispatchSession( sessionId, { type: 'question_answered', question, answer } );
@@ -605,6 +625,7 @@ export function useAgentRun( sessionId: string | undefined ): LiveAgentEvents {
 		isInterrupting,
 		pendingQuestions,
 		pendingAnswers,
+		answeredQuestions,
 		queuedPrompts,
 	} = state;
 
@@ -703,6 +724,7 @@ export function useAgentRun( sessionId: string | undefined ): LiveAgentEvents {
 		error,
 		pendingQuestions,
 		pendingAnswers,
+		answeredQuestions,
 		queuedPrompts,
 		sendMessage,
 		interrupt,