feat: enhance ask_followup_question to support multiple questions

packages/types/src/followup.ts

@@ -8,6 +8,8 @@ import { z } from "zod"
 export interface FollowUpData {
 	/** The question being asked by the LLM */
 	question?: string
+	/** Array of questions being asked by the LLM */
+	questions?: string[]
 	/** Array of suggested answers that the user can select */
 	suggest?: Array<SuggestionItem>
 }
@@ -35,6 +37,7 @@ export const suggestionItemSchema = z.object({
  */
 export const followUpDataSchema = z.object({
 	question: z.string().optional(),
+	questions: z.array(z.string()).optional(),
 	suggest: z.array(suggestionItemSchema).optional(),
 })
 

src/core/prompts/tools/ask-followup-question.ts

@@ -1,10 +1,11 @@
 export function getAskFollowupQuestionDescription(): string {
 	return `## ask_followup_question
-Description: Ask the user a question to gather additional information needed to complete the task. Use when you need clarification or more details to proceed effectively.
+Description: Ask the user a question to gather additional information needed to complete the task. Use when you need clarification or more details to proceed effectively. You may ask multiple questions at once.
 
 Parameters:
-- question: (required) A clear, specific question addressing the information needed
-- follow_up: (required) A list of 2-4 suggested answers, each in its own <suggest> tag. Suggestions must be complete, actionable answers without placeholders. Optionally include mode attribute to switch modes (code/architect/etc.)
+- question: (required) A clear, specific question addressing the information needed.
+- questions: (optional) A container for asking multiple questions. Use <question> tags inside.
+- follow_up: (optional) A list of suggested answers, each in its own <suggest> tag.
 
 Usage:
 <ask_followup_question>
@@ -15,6 +16,14 @@ Usage:
 </follow_up>
 </ask_followup_question>
 
+Usage with multiple questions:
+<ask_followup_question>
+<questions>
+<question>Question 1?</question>
+<question>Question 2?</question>
+</questions>
+</ask_followup_question>
+
 Example:
 <ask_followup_question>
 <question>What is the path to the frontend-config.json file?</question>

src/core/tools/AskFollowupQuestionTool.ts

@@ -12,6 +12,7 @@ interface Suggestion {
 
 interface AskFollowupQuestionParams {
 	question: string
+	questions?: string[]
 	follow_up: Suggestion[]
 }
 
@@ -20,9 +21,33 @@ export class AskFollowupQuestionTool extends BaseTool<"ask_followup_question"> {
 
 	parseLegacy(params: Partial<Record<string, string>>): AskFollowupQuestionParams {
 		const question = params.question || ""
+		const questions_xml = params.questions
 		const follow_up_xml = params.follow_up
 
 		const suggestions: Suggestion[] = []
+		const questions: string[] = []
+
+		if (questions_xml) {
+			try {
+				const parsedQuestions = parseXml(questions_xml, ["question"]) as {
+					question: string[] | string
+				}
+
+				const rawQuestions = Array.isArray(parsedQuestions?.question)
+					? parsedQuestions.question
+					: [parsedQuestions?.question].filter((q): q is string => q !== undefined)
+
+				for (const q of rawQuestions) {
+					if (typeof q === "string") {
+						questions.push(q)
+					}
+				}
+			} catch (error) {
+				throw new Error(
+					`Failed to parse questions XML: ${error instanceof Error ? error.message : String(error)}`,
+				)
+			}
+		}
 
 		if (follow_up_xml) {
 			// Define the actual structure returned by the XML parser
@@ -60,16 +85,17 @@ export class AskFollowupQuestionTool extends BaseTool<"ask_followup_question"> {
 
 		return {
 			question,
+			questions,
 			follow_up: suggestions,
 		}
 	}
 
 	async execute(params: AskFollowupQuestionParams, task: Task, callbacks: ToolCallbacks): Promise<void> {
-		const { question, follow_up } = params
+		const { question, questions, follow_up } = params
 		const { handleError, pushToolResult, toolProtocol } = callbacks
 
 		try {
-			if (!question) {
+			if (!question && (!questions || questions.length === 0)) {
 				task.consecutiveMistakeCount++
 				task.recordToolError("ask_followup_question")
 				task.didToolFailInCurrentTurn = true
@@ -80,6 +106,7 @@ export class AskFollowupQuestionTool extends BaseTool<"ask_followup_question"> {
 			// Transform follow_up suggestions to the format expected by task.ask
 			const follow_up_json = {
 				question,
+				questions,
 				suggest: follow_up.map((s) => ({ answer: s.text, mode: s.mode })),
 			}
 
@@ -95,6 +122,8 @@ export class AskFollowupQuestionTool extends BaseTool<"ask_followup_question"> {
 	override async handlePartial(task: Task, block: ToolUse<"ask_followup_question">): Promise<void> {
 		// Get question from params (for XML protocol) or nativeArgs (for native protocol)
 		const question: string | undefined = block.params.question ?? block.nativeArgs?.question
+		// For now we don't stream multiple questions, only the main one if present
+		// We could improve this to stream multiple questions but it requires UI changes to handle partial arrays
 
 		// During partial streaming, only show the question to avoid displaying raw JSON
 		// The full JSON with suggestions will be sent when the tool call is complete (!block.partial)

src/core/tools/__tests__/askFollowupQuestionTool.spec.ts

@@ -103,6 +103,32 @@ describe("askFollowupQuestionTool", () => {
 		)
 	})
 
+	it("should parse multiple questions from XML", async () => {
+		const block: ToolUse = {
+			type: "tool_use",
+			name: "ask_followup_question",
+			params: {
+				questions: "<question>Question 1</question><question>Question 2</question>",
+				follow_up: "",
+			},
+			partial: false,
+		}
+
+		await askFollowupQuestionTool.handle(mockCline, block as ToolUse<"ask_followup_question">, {
+			askApproval: vi.fn(),
+			handleError: vi.fn(),
+			pushToolResult: mockPushToolResult,
+			removeClosingTag: vi.fn((tag, content) => content),
+			toolProtocol: "xml",
+		})
+
+		expect(mockCline.ask).toHaveBeenCalledWith(
+			"followup",
+			expect.stringContaining('"questions":["Question 1","Question 2"]'),
+			false,
+		)
+	})
+
 	describe("handlePartial with native protocol", () => {
 		it("should only send question during partial streaming to avoid raw JSON display", async () => {
 			const block: ToolUse<"ask_followup_question"> = {

src/shared/tools.ts

@@ -76,6 +76,7 @@ export const toolParamNames = [
 	"old_string", // search_replace and edit_file parameter
 	"new_string", // search_replace and edit_file parameter
 	"expected_replacements", // edit_file parameter for multiple occurrences
+	"questions", // ask_followup_question parameter for multiple questions
 ] as const
 
 export type ToolParamName = (typeof toolParamNames)[number]

webview-ui/src/components/chat/ChatRow.tsx

@@ -38,6 +38,7 @@ import McpResourceRow from "../mcp/McpResourceRow"
 import { Mention } from "./Mention"
 import { CheckpointSaved } from "./checkpoints/CheckpointSaved"
 import { FollowUpSuggest } from "./FollowUpSuggest"
+import { MultiQuestionHandler } from "./MultiQuestionHandler"
 import { BatchFilePermission } from "./BatchFilePermission"
 import { BatchDiffApproval } from "./BatchDiffApproval"
 import { ProgressIndicator } from "./ProgressIndicator"
@@ -1632,17 +1633,28 @@ export const ChatRowContent = ({
 								</div>
 							)}
 							<div className="flex flex-col gap-2 ml-6">
-								<Markdown
-									markdown={message.partial === true ? message?.text : followUpData?.question}
-								/>
-								<FollowUpSuggest
-									suggestions={followUpData?.suggest}
-									onSuggestionClick={onSuggestionClick}
-									ts={message?.ts}
-									onCancelAutoApproval={onFollowUpUnmount}
-									isAnswered={isFollowUpAnswered}
-									isFollowUpAutoApprovalPaused={isFollowUpAutoApprovalPaused}
-								/>
+								{followUpData?.questions && followUpData.questions.length > 0 ? (
+									<MultiQuestionHandler
+										questions={followUpData.questions}
+										onSendResponse={(response) => {
+											onSuggestionClick?.({ answer: response })
+										}}
+									/>
+								) : (
+									<>
+										<Markdown
+											markdown={message.partial === true ? message?.text : followUpData?.question}
+										/>
+										<FollowUpSuggest
+											suggestions={followUpData?.suggest}
+											onSuggestionClick={onSuggestionClick}
+											ts={message?.ts}
+											onCancelAutoApproval={onFollowUpUnmount}
+											isAnswered={isFollowUpAnswered}
+											isFollowUpAutoApprovalPaused={isFollowUpAutoApprovalPaused}
+										/>
+									</>
+								)}
 							</div>
 						</>
 					)

webview-ui/src/components/chat/MultiQuestionHandler.tsx

@@ -0,0 +1,76 @@
+import React, { useState, useEffect } from "react"
+import { Button, Textarea } from "@/components/ui"
+import { useAppTranslation } from "@src/i18n/TranslationContext"
+
+interface MultiQuestionHandlerProps {
+	questions: string[]
+	onSendResponse: (response: string) => void
+}
+
+export const MultiQuestionHandler = ({ questions, onSendResponse }: MultiQuestionHandlerProps) => {
+	const { t } = useAppTranslation()
+	const [currentQuestionIndex, setCurrentQuestionIndex] = useState(0)
+	const [answers, setAnswers] = useState<string[]>(new Array(questions.length).fill(""))
+	const [inputValue, setInputValue] = useState("")
+
+	useEffect(() => {
+		setInputValue(answers[currentQuestionIndex] || "")
+	}, [currentQuestionIndex, answers])
+
+	const handleNext = () => {
+		const newAnswers = [...answers]
+		newAnswers[currentQuestionIndex] = inputValue
+		setAnswers(newAnswers)
+
+		if (currentQuestionIndex < questions.length - 1) {
+			setCurrentQuestionIndex(currentQuestionIndex + 1)
+		} else {
+			// Finish
+			const combined = questions
+				.map((q, i) => `Question: ${q}\nAnswer: ${newAnswers[i] || "(skipped)"}`)
+				.join("\n\n")
+			onSendResponse(combined)
+		}
+	}
+
+	const handlePrevious = () => {
+		const newAnswers = [...answers]
+		newAnswers[currentQuestionIndex] = inputValue
+		setAnswers(newAnswers)
+
+		if (currentQuestionIndex > 0) {
+			setCurrentQuestionIndex(currentQuestionIndex - 1)
+		}
+	}
+
+	return (
+		<div className="flex flex-col gap-3">
+			<div className="font-bold">
+				{t("chat:questions.questionNumberOfTotal", {
+					current: currentQuestionIndex + 1,
+					total: questions.length,
+				})}
+			</div>
+			<div>{questions[currentQuestionIndex]}</div>
+			<Textarea
+				value={inputValue}
+				onChange={(e) => setInputValue(e.target.value)}
+				rows={3}
+				placeholder={t("chat:questions.typeAnswer")}
+				className="w-full"
+			/>
+			<div className="flex gap-2">
+				{currentQuestionIndex > 0 && (
+					<Button variant="secondary" onClick={handlePrevious}>
+						{t("chat:questions.previous")}
+					</Button>
+				)}
+				<Button variant="primary" onClick={handleNext}>
+					{currentQuestionIndex < questions.length - 1
+						? t("chat:questions.next")
+						: t("chat:questions.finish")}
+				</Button>
+			</div>
+		</div>
+	)
+}

webview-ui/src/i18n/locales/en/chat.json

@@ -287,7 +287,12 @@
 		"completionInstructions": "Subtask completed! You can review the results and suggest any corrections or next steps. If everything looks good, confirm to return the result to the parent task."
 	},
 	"questions": {
-		"hasQuestion": "Roo has a question"
+		"hasQuestion": "Roo has a question",
+		"questionNumberOfTotal": "Question {{current}} of {{total}}",
+		"typeAnswer": "Type your answer here...",
+		"previous": "Previous",
+		"next": "Next",
+		"finish": "Finish"
 	},
 	"taskCompleted": "Task Completed",
 	"error": "Error",