diff --git a/backend/open_webui/tools/builtin.py b/backend/open_webui/tools/builtin.py
index ac9a36066d..dc7d9f9dd3 100644
--- a/backend/open_webui/tools/builtin.py
+++ b/backend/open_webui/tools/builtin.py
@@ -498,6 +498,114 @@ async def edit_image(
         return JSONCodec.dumps({'error': str(e)})
 
 
+# =============================================================================
+# USER INPUT TOOLS
+# =============================================================================
+
+
+async def ask_user(
+    questions: list[dict],
+    allow_other: bool = True,
+    __event_call__: callable = None,
+) -> str:
+    """
+    Ask the user clarifying questions before continuing.
+    Use this when the next step depends on user intent, preference, or a tradeoff that cannot be inferred safely.
+
+    :param questions: 1-3 question objects, each with id, header, question, and 2-3 options. Each option needs label and description.
+    :param allow_other: Whether users may enter a free-form answer instead of choosing one of the options
+    :return: JSON with status and answers keyed by question id
+    """
+    try:
+        if not isinstance(questions, list) or not 1 <= len(questions) <= 3:
+            raise ValueError('ask_user requires 1-3 questions.')
+
+        normalized_questions = []
+        seen_ids = set()
+        for index, question in enumerate(questions):
+            if not isinstance(question, dict):
+                raise ValueError('Each question must be an object.')
+
+            question_id = str(question.get('id') or '').strip()[:64]
+            if not question_id:
+                raise ValueError('Each question requires a non-empty id.')
+            if question_id in seen_ids:
+                raise ValueError(f'Duplicate question id: {question_id}')
+            seen_ids.add(question_id)
+
+            options = question.get('options')
+            if not isinstance(options, list) or not 2 <= len(options) <= 3:
+                raise ValueError('Each question requires 2-3 options.')
+
+            normalized_options = []
+            for option in options:
+                if not isinstance(option, dict):
+                    raise ValueError('Each option must be an object.')
+
+                label = str(option.get('label') or '').strip()[:80]
+                description = str(option.get('description') or '').strip()[:240]
+                if not label or not description:
+                    raise ValueError('Each option requires a label and description.')
+
+                normalized_options.append(
+                    {
+                        'label': label,
+                        'description': description,
+                    }
+                )
+
+            question_text = str(question.get('question') or '').strip()[:500]
+            if not question_text:
+                raise ValueError('Each question requires question text.')
+
+            normalized_questions.append(
+                {
+                    'id': question_id,
+                    'header': str(question.get('header') or '').strip()[:48] or f'Question {index + 1}',
+                    'question': question_text,
+                    'options': normalized_options,
+                    'allow_other': bool(question.get('allow_other', allow_other)),
+                }
+            )
+
+        if __event_call__ is None:
+            return JSONCodec.dumps(
+                {
+                    'status': 'error',
+                    'error': 'User input requires an active browser session with WebSocket connection.',
+                },
+                ensure_ascii=False,
+            )
+
+        output = await __event_call__(
+            {
+                'type': 'request:user_input',
+                'data': {
+                    'questions': normalized_questions,
+                    'allow_other': allow_other,
+                },
+            }
+        )
+
+        if not isinstance(output, dict):
+            return JSONCodec.dumps({'status': 'error', 'error': 'Invalid user input response.'}, ensure_ascii=False)
+        if output.get('error'):
+            return JSONCodec.dumps({'status': 'error', 'error': output.get('error')}, ensure_ascii=False)
+        if output.get('status') == 'cancelled':
+            return JSONCodec.dumps({'status': 'cancelled', 'answers': {}}, ensure_ascii=False)
+
+        return JSONCodec.dumps(
+            {
+                'status': 'answered',
+                'answers': output.get('answers', {}),
+            },
+            ensure_ascii=False,
+        )
+    except Exception as e:
+        log.exception(f'ask_user error: {e}')
+        return JSONCodec.dumps({'status': 'error', 'error': str(e)}, ensure_ascii=False)
+
+
 # =============================================================================
 # CODE INTERPRETER TOOLS
 # =============================================================================
diff --git a/backend/open_webui/utils/tools.py b/backend/open_webui/utils/tools.py
index 5a3852b89d..bb682d4cdb 100644
--- a/backend/open_webui/utils/tools.py
+++ b/backend/open_webui/utils/tools.py
@@ -47,6 +47,7 @@ from open_webui.models.tools import Tools
 from open_webui.models.users import UserModel
 from open_webui.tools.builtin import (
     add_memory,
+    ask_user,
     calculate_timestamp,
     create_automation,
     create_calendar_event,
@@ -583,6 +584,9 @@ async def get_builtin_tools(
     if is_builtin_tool_enabled('time'):
         builtin_functions.extend([get_current_timestamp, calculate_timestamp])
 
+    if is_builtin_tool_enabled('user_input'):
+        builtin_functions.append(ask_user)
+
     metadata = extra_params.get('__metadata__') or {}
     chat_files = metadata.get('files') or extra_params.get('__files__') or []
     has_chat_files = any(
diff --git a/src/lib/components/chat/AskUserCard.svelte b/src/lib/components/chat/AskUserCard.svelte
new file mode 100644
index 0000000000..4c69789c04
--- /dev/null
+++ b/src/lib/components/chat/AskUserCard.svelte
@@ -0,0 +1,296 @@
+<script lang="ts">
+	import { createEventDispatcher, getContext } from 'svelte';
+	import type { Writable } from 'svelte/store';
+	import type { i18n as i18nType } from 'i18next';
+
+	const i18n: Writable<i18nType> = getContext('i18n');
+	const dispatch = createEventDispatcher();
+
+	type AskUserOption = {
+		label: string;
+		description: string;
+	};
+
+	type AskUserQuestion = {
+		id: string;
+		header: string;
+		question: string;
+		options: AskUserOption[];
+		allow_other?: boolean;
+	};
+
+	type DraftAnswer =
+		| {
+				type: 'option';
+				option_index: number;
+				label: string;
+				description: string;
+		  }
+		| {
+				type: 'other';
+				text: string;
+		  };
+
+	export let show = false;
+	export let questions: AskUserQuestion[] = [];
+	export let allowOther = true;
+
+	let answers: Record<string, DraftAnswer> = {};
+	let questionIndex = 0;
+	let wasOpen = false;
+
+	$: if (show && !wasOpen) {
+		answers = {};
+		questionIndex = 0;
+		wasOpen = true;
+	}
+
+	$: if (!show && wasOpen) {
+		wasOpen = false;
+	}
+
+	const questionAllowsOther = (question: AskUserQuestion) => question.allow_other ?? allowOther;
+
+	$: question = questions[questionIndex];
+	$: selectedAnswer = question ? answers[question.id] : undefined;
+
+	const hasAnswers = (selected = answers) =>
+		questions.length > 0 &&
+		questions.every((question) => {
+			const answer = selected[question.id];
+			return answer?.type === 'option' || (answer?.type === 'other' && answer.text.trim() !== '');
+		});
+
+	$: complete = hasAnswers();
+
+	const submit = (selected = answers) => {
+		if (!hasAnswers(selected)) {
+			return;
+		}
+
+		const normalized: Record<string, DraftAnswer> = {};
+		for (const question of questions) {
+			const answer = selected[question.id];
+			if (answer?.type === 'option') {
+				normalized[question.id] = answer;
+			} else if (answer?.type === 'other') {
+				normalized[question.id] = {
+					type: 'other',
+					text: answer.text.trim()
+				};
+			}
+		}
+
+		show = false;
+		dispatch('confirm', {
+			status: 'answered',
+			answers: normalized
+		});
+	};
+
+	const advance = (selected = answers) => {
+		if (questionIndex < questions.length - 1) {
+			questionIndex += 1;
+		} else if (hasAnswers(selected)) {
+			submit(selected);
+		}
+	};
+
+	const selectOption = (question: AskUserQuestion, option: AskUserOption, index: number) => {
+		const selected: Record<string, DraftAnswer> = {
+			...answers,
+			[question.id]: {
+				type: 'option',
+				option_index: index,
+				label: option.label,
+				description: option.description
+			}
+		};
+		answers = selected;
+		advance(selected);
+	};
+
+	const selectOther = (question: AskUserQuestion) => {
+		const existing = answers[question.id];
+		answers = {
+			...answers,
+			[question.id]: {
+				type: 'other',
+				text: existing?.type === 'other' ? existing.text : ''
+			}
+		};
+	};
+
+	const updateOther = (question: AskUserQuestion, text: string) => {
+		answers = {
+			...answers,
+			[question.id]: {
+				type: 'other',
+				text
+			}
+		};
+	};
+
+	const isSelectedOption = (question: AskUserQuestion, index: number) => {
+		const answer = answers[question.id];
+		return answer?.type === 'option' && answer.option_index === index;
+	};
+
+	const isSelectedOther = (question: AskUserQuestion) => answers[question.id]?.type === 'other';
+
+	const otherText = (question: AskUserQuestion) => {
+		const answer = answers[question.id];
+		return answer?.type === 'other' ? answer.text : '';
+	};
+</script>
+
+{#if show}
+	<section class="my-1 rounded-2xl bg-gray-100/70 px-3.5 py-3 dark:bg-white/[0.055]">
+		<div class="mb-3 flex items-center justify-between gap-3">
+			<div class="text-[0.6875rem] font-medium tracking-wide text-gray-500 dark:text-gray-400">
+				{$i18n.t('Planning question')}
+			</div>
+			<div class="text-[0.6875rem] text-gray-500 dark:text-gray-400">
+				{$i18n.t('Question')}
+				{questionIndex + 1}
+				{$i18n.t('of')}
+				{questions.length} ·
+				{$i18n.t('Paused while visible')}
+			</div>
+		</div>
+
+		<div class="space-y-2.5">
+			{#if question}
+				{#key question.id}
+					<div class="space-y-2.5">
+						<div>
+							<div class="text-sm font-medium tracking-[-0.01em] text-gray-900 dark:text-gray-100">
+								{question.header}
+							</div>
+							<div class="mt-1 text-xs leading-relaxed text-gray-600 dark:text-gray-300">
+								{question.question}
+							</div>
+						</div>
+
+						<div class="space-y-0.5">
+							{#each question.options || [] as option, optionIndex}
+								<!-- svelte-ignore a11y_click_events_have_key_events -->
+								<!-- svelte-ignore a11y_no_noninteractive_element_interactions -->
+								<label
+									class="flex cursor-pointer items-start gap-2.5 rounded-xl px-2.5 py-1.5 transition-colors {isSelectedOption(
+										question,
+										optionIndex
+									)
+										? 'bg-white shadow-sm dark:bg-white/[0.1]'
+										: 'hover:bg-white/70 dark:hover:bg-white/[0.06]'}"
+									on:click={() => isSelectedOption(question, optionIndex) && advance()}
+								>
+									<input
+										class="sr-only"
+										type="radio"
+										name={question.id}
+										value={option.label}
+										checked={isSelectedOption(question, optionIndex)}
+										on:change={() => selectOption(question, option, optionIndex)}
+									/>
+									<span
+										class="mt-1 flex size-3.5 shrink-0 items-center justify-center rounded-full border {isSelectedOption(
+											question,
+											optionIndex
+										)
+											? 'border-gray-900 dark:border-white'
+											: 'border-gray-300 dark:border-white/25'}"
+									>
+										{#if isSelectedOption(question, optionIndex)}
+											<span class="size-1.5 rounded-full bg-gray-900 dark:bg-white"></span>
+										{/if}
+									</span>
+									<span class="min-w-0 text-xs">
+										<span class="text-gray-800 dark:text-gray-100">{option.label}</span>
+										{#if optionIndex === 0}
+											<span class="ml-1.5 text-[0.625rem] text-gray-400 dark:text-gray-500">
+												{$i18n.t('Recommended')}
+											</span>
+										{/if}
+										<span class="mt-0.5 block leading-relaxed text-gray-500 dark:text-gray-400">
+											{option.description}
+										</span>
+									</span>
+								</label>
+							{/each}
+
+							{#if questionAllowsOther(question)}
+								<label
+									class="flex cursor-pointer items-center gap-2.5 rounded-xl px-2.5 py-1.5 text-xs transition-colors {isSelectedOther(
+										question
+									)
+										? 'bg-white shadow-sm dark:bg-white/[0.1]'
+										: 'hover:bg-white/70 dark:hover:bg-white/[0.06]'}"
+								>
+									<input
+										class="sr-only"
+										type="radio"
+										name={question.id}
+										value="__other__"
+										checked={isSelectedOther(question)}
+										on:change={() => selectOther(question)}
+									/>
+									<span
+										class="flex size-3.5 shrink-0 items-center justify-center rounded-full border {isSelectedOther(
+											question
+										)
+											? 'border-gray-900 dark:border-white'
+											: 'border-gray-300 dark:border-white/25'}"
+									>
+										{#if selectedAnswer?.type === 'other'}
+											<span class="size-1.5 rounded-full bg-gray-900 dark:bg-white"></span>
+										{/if}
+									</span>
+									<span class="text-gray-700 dark:text-gray-200">{$i18n.t('Other')}</span>
+								</label>
+								{#if selectedAnswer?.type === 'other'}
+									<input
+										class="w-full rounded-xl bg-transparent px-2.5 py-1.5 text-xs text-gray-800 outline-none placeholder:text-gray-400 dark:text-gray-100 dark:placeholder:text-gray-500"
+										placeholder={$i18n.t('Type your answer')}
+										value={otherText(question)}
+										on:input={(event) =>
+											updateOther(question, (event.currentTarget as HTMLInputElement).value)}
+									/>
+								{/if}
+							{/if}
+						</div>
+					</div>
+				{/key}
+			{/if}
+
+			<div class="flex items-center justify-between gap-2 pt-0.5">
+				<button
+					type="button"
+					class="rounded-lg px-2.5 py-1.5 text-xs text-gray-500 transition-colors hover:bg-white/70 hover:text-gray-800 disabled:opacity-30 dark:text-gray-400 dark:hover:bg-white/10 dark:hover:text-gray-100"
+					disabled={questionIndex === 0}
+					on:click={() => (questionIndex -= 1)}
+				>
+					{$i18n.t('Previous')}
+				</button>
+				{#if questionIndex < questions.length - 1}
+					<button
+						type="button"
+						class="rounded-lg bg-gray-900 px-3 py-1.5 text-xs font-medium text-white transition hover:bg-gray-800 active:scale-[0.98] dark:bg-white dark:text-black dark:hover:bg-white/90"
+						on:click={() => (questionIndex += 1)}
+					>
+						{$i18n.t('Next')}
+					</button>
+				{:else}
+					<button
+						type="button"
+						class="rounded-lg bg-gray-900 px-3 py-1.5 text-xs font-medium text-white transition hover:bg-gray-800 active:scale-[0.98] disabled:cursor-not-allowed disabled:opacity-40 dark:bg-white dark:text-black dark:hover:bg-white/90"
+						disabled={!complete}
+						on:click={() => submit()}
+					>
+						{$i18n.t('Submit answers')}
+					</button>
+				{/if}
+			</div>
+		</div>
+	</section>
+{/if}
diff --git a/src/lib/components/chat/Chat.svelte b/src/lib/components/chat/Chat.svelte
index dc9f6653f7..9f168455dc 100644
--- a/src/lib/components/chat/Chat.svelte
+++ b/src/lib/components/chat/Chat.svelte
@@ -162,7 +162,10 @@
 	let eventConfirmationInputValue = '';
 	let eventConfirmationInputType = '';
 	let eventConfirmationInputOptions: ({ label?: string; value: string } | string)[] = [];
-	let eventCallback = null;
+	let eventCallback: (value: any) => void = () => {};
+	let showAskUserDialog = false;
+	let askUserQuestions: any[] = [];
+	let askUserAllowOther = true;
 
 	let selectedModels = [''];
 	let atSelectedModel: Model | undefined;
@@ -1144,6 +1147,11 @@
 					eventConfirmationInputValue = data?.value ?? '';
 					eventConfirmationInputType = data?.input?.type ?? data?.type ?? '';
 					eventConfirmationInputOptions = data?.input?.options ?? data?.options ?? [];
+				} else if (type === 'request:user_input') {
+					eventCallback = cb;
+					askUserQuestions = data?.questions ?? [];
+					askUserAllowOther = data?.allow_other ?? true;
+					showAskUserDialog = true;
 				} else if (type.startsWith('terminal:')) {
 					terminalEventHandler(type, data);
 				} else {
@@ -1600,7 +1608,9 @@
 						fileItem.content_type = uploadedFile.meta?.content_type;
 						fileItem.size = uploadedFile.meta?.size;
 						fileItem.collection_name =
-							res.collection_name ?? uploadedFile.meta?.collection_name ?? uploadedFile.collection_name;
+							res.collection_name ??
+							uploadedFile.meta?.collection_name ??
+							uploadedFile.collection_name;
 					} else {
 						fileItem.type = 'text';
 						fileItem.file = {
@@ -2249,9 +2259,7 @@
 
 			chatRequestQueues.update((q) => ({
 				...q,
-				[targetChatId]: (q[targetChatId] ?? []).filter(
-					(m) => !queuedMessageIds.has(m.id)
-				)
+				[targetChatId]: (q[targetChatId] ?? []).filter((m) => !queuedMessageIds.has(m.id))
 			}));
 
 			await submitPrompt(combinedPrompt, combinedFiles);
@@ -4165,6 +4173,15 @@
 										{onUpdate}
 										messageQueue={$chatRequestQueues[$chatId] ?? []}
 										{chatTasks}
+										askUser={{
+											show: showAskUserDialog,
+											questions: askUserQuestions,
+											allowOther: askUserAllowOther,
+											onConfirm: (value) => {
+												showAskUserDialog = false;
+												eventCallback(value);
+											}
+										}}
 										onQueueSendNow={sendQueuedMessageNow}
 										onQueueEdit={editQueuedMessage}
 										onQueueDelete={deleteQueuedMessage}
@@ -4219,10 +4236,7 @@
 										</div>
 									</div>
 								{/if}
-								<div
-									id={embedded ? messageInputDropzoneId : undefined}
-									class="pb-2 z-10"
-								>
+								<div id={embedded ? messageInputDropzoneId : undefined} class="pb-2 z-10">
 									<MessageInput
 										bind:this={messageInput}
 										{history}
@@ -4257,6 +4271,15 @@
 										{onUpdate}
 										messageQueue={$chatRequestQueues[$chatId] ?? []}
 										{chatTasks}
+										askUser={{
+											show: showAskUserDialog,
+											questions: askUserQuestions,
+											allowOther: askUserAllowOther,
+											onConfirm: (value) => {
+												showAskUserDialog = false;
+												eventCallback(value);
+											}
+										}}
 										onQueueSendNow={sendQueuedMessageNow}
 										onQueueEdit={editQueuedMessage}
 										onQueueDelete={deleteQueuedMessage}
diff --git a/src/lib/components/chat/MessageInput.svelte b/src/lib/components/chat/MessageInput.svelte
index 0b6be97771..6b40cec2b9 100644
--- a/src/lib/components/chat/MessageInput.svelte
+++ b/src/lib/components/chat/MessageInput.svelte
@@ -104,6 +104,7 @@
 	import Knobs from '../icons/Knobs.svelte';
 	import ValvesModal from '../workspace/common/ValvesModal.svelte';
 	import Note from '../icons/Note.svelte';
+	import AskUserCard from './AskUserCard.svelte';
 	import { goto } from '$app/navigation';
 	import InputModal from '../common/InputModal.svelte';
 	import Expand from '../icons/Expand.svelte';
@@ -170,6 +171,12 @@
 	export let onQueueEdit: (id: string) => void = () => {};
 	export let onQueueDelete: (id: string) => void = () => {};
 	export let onUpdate: (data?: { file?: any }) => void = () => {};
+	export let askUser = {
+		show: false,
+		questions: [],
+		allowOther: true,
+		onConfirm: (_value: any) => {}
+	};
 
 	export let chatTasks = [];
 
@@ -1580,6 +1587,19 @@
 							on:click={() => createMessagePair(prompt)}
 						/>
 
+						{#if askUser?.show}
+							<div class="mx-1">
+								<AskUserCard
+									show={askUser.show}
+									questions={askUser.questions}
+									allowOther={askUser.allowOther}
+									on:confirm={(e) => {
+										askUser.onConfirm(e.detail);
+									}}
+								/>
+							</div>
+						{/if}
+
 						<!-- Task list display -->
 						{#if isActive && chatTasks.length > 0}
 							<div class="mx-1">
diff --git a/src/lib/components/workspace/Models/BuiltinTools.svelte b/src/lib/components/workspace/Models/BuiltinTools.svelte
index 38e37cbc3e..b91626aa94 100644
--- a/src/lib/components/workspace/Models/BuiltinTools.svelte
+++ b/src/lib/components/workspace/Models/BuiltinTools.svelte
@@ -1,16 +1,22 @@
 <script lang="ts">
 	import { getContext } from 'svelte';
+	import type { Writable } from 'svelte/store';
+	import type { i18n as i18nType } from 'i18next';
 	import Checkbox from '$lib/components/common/Checkbox.svelte';
 	import Tooltip from '$lib/components/common/Tooltip.svelte';
 	import { marked } from 'marked';
 
-	const i18n = getContext('i18n');
+	const i18n: Writable<i18nType> = getContext('i18n');
 
 	const toolLabels = {
 		time: {
 			label: $i18n.t('Time & Calculation'),
 			description: $i18n.t('Get current time and perform date/time calculations')
 		},
+		user_input: {
+			label: $i18n.t('Ask User'),
+			description: $i18n.t('Pause a response to ask the user a clarifying question')
+		},
 		memory: {
 			label: $i18n.t('Memory'),
 			description: $i18n.t('Search and manage user memories')