src-tauri/src/bridge_manager.rs

@@ -79,6 +79,14 @@ impl BridgeManager {
         }
     }
 
+    pub fn send_tool_result(&mut self, conversation_id: &str, tool_use_id: &str, result: serde_json::Value) -> Result<(), String> {
+        if let Some(bridge) = self.bridges.get_mut(conversation_id) {
+            bridge.send_tool_result(tool_use_id, result)
+        } else {
+            Err("No Claude instance found for this conversation".to_string())
+        }
+    }
+
     pub fn is_claude_running(&self, conversation_id: &str) -> bool {
         self.bridges.get(conversation_id)
             .map(|b| b.is_running())

src-tauri/src/commands.rs

@@ -169,3 +169,14 @@ pub async fn load_saved_achievements(app: AppHandle) -> Result<Vec<AchievementUn
 
     Ok(events)
 }
+
+#[tauri::command]
+pub async fn answer_question(
+    bridge_manager: State<'_, SharedBridgeManager>,
+    conversation_id: String,
+    tool_use_id: String,
+    answers: serde_json::Value,
+) -> Result<(), String> {
+    let mut manager = bridge_manager.lock();
+    manager.send_tool_result(&conversation_id, &tool_use_id, answers)
+}

src-tauri/src/lib.rs

@@ -47,6 +47,7 @@ pub fn run() {
             save_config,
             get_usage_stats,
             load_saved_achievements,
+            answer_question,
             send_windows_notification,
             send_simple_notification,
             send_windows_toast,

src-tauri/src/types.rs

@@ -216,6 +216,24 @@ pub struct WorkingDirectoryEvent {
     pub conversation_id: Option<String>,
 }
 
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct QuestionOption {
+    pub label: String,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub description: Option<String>,
+}
+
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct UserQuestionEvent {
+    pub id: String,
+    pub question: String,
+    pub header: Option<String>,
+    pub options: Vec<QuestionOption>,
+    pub multi_select: bool,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub conversation_id: Option<String>,
+}
+
 #[cfg(test)]
 mod tests {
     use super::*;

src-tauri/src/wsl_bridge.rs

@@ -11,7 +11,7 @@ use std::os::windows::process::CommandExt;
 use crate::config::ClaudeStartOptions;
 use crate::stats::{UsageStats, StatsUpdateEvent};
 use parking_lot::RwLock;
-use crate::types::{CharacterState, ClaudeMessage, ConnectionStatus, ContentBlock, StateChangeEvent, OutputEvent, PermissionPromptEvent, ConnectionEvent, SessionEvent, WorkingDirectoryEvent};
+use crate::types::{CharacterState, ClaudeMessage, ConnectionStatus, ContentBlock, StateChangeEvent, OutputEvent, PermissionPromptEvent, ConnectionEvent, SessionEvent, WorkingDirectoryEvent, UserQuestionEvent, QuestionOption};
 use crate::achievements::{get_achievement_info, AchievementUnlockedEvent};
 
 const SEARCH_TOOLS: [&str; 5] = ["Read", "Glob", "Grep", "WebSearch", "WebFetch"];
@@ -350,6 +350,35 @@ impl WslBridge {
         Ok(())
     }
 
+    pub fn send_tool_result(&mut self, tool_use_id: &str, result: serde_json::Value) -> Result<(), String> {
+        let stdin = self.stdin.as_mut().ok_or("Process not running")?;
+
+        // The content should be a JSON string representation of the result
+        let content_str = serde_json::to_string(&result).map_err(|e| e.to_string())?;
+
+        let input = serde_json::json!({
+            "type": "user",
+            "message": {
+                "role": "user",
+                "content": [{
+                    "type": "tool_result",
+                    "tool_use_id": tool_use_id,
+                    "content": content_str
+                }]
+            }
+        });
+
+        let json_line = serde_json::to_string(&input).map_err(|e| e.to_string())?;
+
+        stdin
+            .write_all(format!("{}\n", json_line).as_bytes())
+            .map_err(|e| format!("Failed to write to stdin: {}", e))?;
+
+        stdin.flush().map_err(|e| format!("Failed to flush stdin: {}", e))?;
+
+        Ok(())
+    }
+
     pub fn interrupt(&mut self, app: &AppHandle) -> Result<(), String> {
         // Due to persistent bug in Claude Code where ESC/Ctrl+C doesn't work,
         // we have to kill the process. This is the only reliable way to stop it.
@@ -640,19 +669,68 @@ fn process_json_line(line: &str, app: &AppHandle, stats: &Arc<RwLock<UsageStats>
 
             // Check for permission denials and emit prompts for each
             if let Some(denials) = permission_denials {
+                let mut has_regular_denials = false;
+
                 for denial in denials {
-                    let description = format_tool_description(&denial.tool_name, &denial.tool_input);
-                    let _ = app.emit("claude:permission", PermissionPromptEvent {
-                        id: denial.tool_use_id.clone(),
-                        tool_name: denial.tool_name.clone(),
-                        tool_input: denial.tool_input.clone(),
-                        description,
-                        conversation_id: conversation_id.clone(),
-                    });
+                    // Special handling for AskUserQuestion tool
+                    if denial.tool_name == "AskUserQuestion" {
+                        if let Some(questions) = denial.tool_input.get("questions").and_then(|q| q.as_array()) {
+                            // For now, handle the first question (most common case)
+                            if let Some(first_question) = questions.first() {
+                                let question_text = first_question.get("question")
+                                    .and_then(|q| q.as_str())
+                                    .unwrap_or("Claude has a question for you")
+                                    .to_string();
+
+                                let header = first_question.get("header")
+                                    .and_then(|h| h.as_str())
+                                    .map(|s| s.to_string());
+
+                                let multi_select = first_question.get("multiSelect")
+                                    .and_then(|m| m.as_bool())
+                                    .unwrap_or(false);
+
+                                let options: Vec<QuestionOption> = first_question.get("options")
+                                    .and_then(|opts| opts.as_array())
+                                    .map(|opts| {
+                                        opts.iter().filter_map(|opt| {
+                                            let label = opt.get("label").and_then(|l| l.as_str())?;
+                                            let description = opt.get("description")
+                                                .and_then(|d| d.as_str())
+                                                .map(|s| s.to_string());
+                                            Some(QuestionOption {
+                                                label: label.to_string(),
+                                                description,
+                                            })
+                                        }).collect()
+                                    })
+                                    .unwrap_or_default();
+
+                                let _ = app.emit("claude:question", UserQuestionEvent {
+                                    id: denial.tool_use_id.clone(),
+                                    question: question_text,
+                                    header,
+                                    options,
+                                    multi_select,
+                                    conversation_id: conversation_id.clone(),
+                                });
+                            }
+                        }
+                    } else {
+                        has_regular_denials = true;
+                        let description = format_tool_description(&denial.tool_name, &denial.tool_input);
+                        let _ = app.emit("claude:permission", PermissionPromptEvent {
+                            id: denial.tool_use_id.clone(),
+                            tool_name: denial.tool_name.clone(),
+                            tool_input: denial.tool_input.clone(),
+                            description,
+                            conversation_id: conversation_id.clone(),
+                        });
+                    }
                 }
 
-                // Show permission state if there were denials
-                if !denials.is_empty() {
+                // Show permission state if there were any denials (questions or regular)
+                if has_regular_denials || !denials.is_empty() {
                     emit_state_change(app, CharacterState::Permission, None, conversation_id.clone());
                     return Ok(());
                 }

src/lib/components/UserQuestionModal.svelte

@@ -0,0 +1,264 @@
+<script lang="ts">
+  import { invoke } from "@tauri-apps/api/core";
+  import { get } from "svelte/store";
+  import { SvelteSet } from "svelte/reactivity";
+  import { claudeStore, hasQuestionPending } from "$lib/stores/claude";
+  import { characterState } from "$lib/stores/character";
+  import type { UserQuestionEvent } from "$lib/types/messages";
+
+  let isVisible = $state(false);
+  let question: UserQuestionEvent | null = $state(null);
+  let selectedOptions: SvelteSet<string> = new SvelteSet();
+  let customAnswer = $state("");
+  let showCustomInput = $state(false);
+  let grantedToolsList: string[] = $state([]);
+  let workingDirectory = $state("");
+
+  hasQuestionPending.subscribe((pending) => {
+    isVisible = pending;
+    if (!pending) {
+      selectedOptions = new SvelteSet();
+      customAnswer = "";
+      showCustomInput = false;
+    }
+  });
+
+  claudeStore.pendingQuestion.subscribe((q) => {
+    question = q;
+    if (q) {
+      characterState.setState("permission");
+    }
+  });
+
+  claudeStore.grantedTools.subscribe((tools) => {
+    grantedToolsList = Array.from(tools);
+  });
+
+  claudeStore.currentWorkingDirectory.subscribe((dir) => {
+    workingDirectory = dir;
+  });
+
+  function toggleOption(label: string) {
+    if (!question) return;
+
+    if (question.multi_select) {
+      if (selectedOptions.has(label)) {
+        selectedOptions.delete(label);
+      } else {
+        selectedOptions.add(label);
+      }
+    } else {
+      selectedOptions.clear();
+      selectedOptions.add(label);
+    }
+    showCustomInput = false;
+  }
+
+  function selectCustom() {
+    showCustomInput = true;
+    selectedOptions.clear();
+  }
+
+  async function handleSubmitAndReconnect() {
+    if (!question) return;
+
+    const conversationId = get(claudeStore.activeConversationId);
+    if (!conversationId) return;
+
+    let answerText: string;
+
+    if (showCustomInput && customAnswer.trim()) {
+      answerText = customAnswer.trim();
+    } else if (selectedOptions.size > 0) {
+      if (question.multi_select) {
+        answerText = Array.from(selectedOptions).join(", ");
+      } else {
+        answerText = Array.from(selectedOptions)[0];
+      }
+    } else {
+      return;
+    }
+
+    const questionText = question.question;
+    const conversationHistory = claudeStore.getConversationHistory();
+
+    claudeStore.addLine("system", `Answer: ${answerText}. Reconnecting with context...`);
+    claudeStore.clearQuestion();
+
+    try {
+      await invoke("stop_claude", { conversationId });
+
+      await new Promise((resolve) => setTimeout(resolve, 500));
+
+      await invoke("start_claude", {
+        conversationId,
+        options: {
+          working_dir: workingDirectory || "/home/naomi",
+          allowed_tools: grantedToolsList,
+        },
+      });
+
+      await new Promise((resolve) => setTimeout(resolve, 1000));
+
+      if (conversationHistory) {
+        const contextMessage = `[CONTEXT RESTORATION]
+I just answered your question. Here's our conversation so far:
+
+${conversationHistory}
+
+You asked me: "${questionText}"
+My answer: "${answerText}"
+
+Please continue where we left off, taking my answer into account.`;
+
+        await invoke("send_prompt", {
+          conversationId,
+          message: contextMessage,
+        });
+      }
+
+      characterState.setTemporaryState("success", 2000);
+    } catch (error) {
+      console.error("Failed to reconnect:", error);
+      claudeStore.addLine("error", `Reconnect failed: ${error}`);
+      characterState.setTemporaryState("error", 3000);
+    }
+  }
+
+  function handleDismiss() {
+    claudeStore.clearQuestion();
+    claudeStore.addLine("system", "Question dismissed");
+    characterState.setTemporaryState("idle", 1000);
+  }
+
+  function handleKeydown(event: KeyboardEvent) {
+    if (!isVisible || !question) return;
+
+    if (event.key === "Enter" && !showCustomInput) {
+      event.preventDefault();
+      if (selectedOptions.size > 0) {
+        handleSubmitAndReconnect();
+      }
+    } else if (event.key === "Escape") {
+      event.preventDefault();
+      handleDismiss();
+    }
+  }
+
+  function canSubmit(): boolean {
+    return selectedOptions.size > 0 || (showCustomInput && customAnswer.trim().length > 0);
+  }
+</script>
+
+<svelte:window onkeydown={handleKeydown} />
+
+{#if isVisible && question}
+  <div
+    class="question-overlay fixed inset-0 bg-black/70 flex items-center justify-center z-50 backdrop-blur-sm"
+  >
+    <div
+      class="question-modal bg-[var(--bg-primary)] border border-[var(--border-color)] rounded-xl p-6 max-w-md w-full mx-4 shadow-2xl"
+    >
+      <div class="flex items-center gap-3 mb-4">
+        <div class="w-10 h-10 rounded-full bg-blue-500/20 flex items-center justify-center">
+          <span class="text-xl">?</span>
+        </div>
+        <div>
+          <h2 class="text-lg font-semibold text-[var(--text-primary)]">
+            {question.header || "Question"}
+          </h2>
+          <p class="text-sm text-[var(--text-secondary)]">Hikari needs your input</p>
+        </div>
+      </div>
+
+      <div class="mb-4">
+        <p class="text-[var(--text-primary)]">{question.question}</p>
+      </div>
+
+      <div class="mb-4 space-y-2">
+        {#each question.options as option (option.label)}
+          <button
+            onclick={() => toggleOption(option.label)}
+            class="w-full text-left px-4 py-3 rounded-lg border transition-colors {selectedOptions.has(
+              option.label
+            )
+              ? 'bg-[var(--accent-primary)]/20 border-[var(--accent-primary)] text-[var(--text-primary)]'
+              : 'bg-[var(--bg-secondary)] border-[var(--border-color)] text-[var(--text-primary)] hover:border-[var(--accent-primary)]/50'}"
+          >
+            <div class="flex items-start gap-3">
+              <div
+                class="mt-0.5 w-5 h-5 rounded-{question.multi_select
+                  ? 'sm'
+                  : 'full'} border-2 flex items-center justify-center {selectedOptions.has(
+                  option.label
+                )
+                  ? 'border-[var(--accent-primary)] bg-[var(--accent-primary)]'
+                  : 'border-[var(--text-secondary)]'}"
+              >
+                {#if selectedOptions.has(option.label)}
+                  <span class="text-white text-xs">{question.multi_select ? "x" : "x"}</span>
+                {/if}
+              </div>
+              <div class="flex-1">
+                <div class="font-medium">{option.label}</div>
+                {#if option.description}
+                  <div class="text-sm text-[var(--text-secondary)] mt-1">{option.description}</div>
+                {/if}
+              </div>
+            </div>
+          </button>
+        {/each}
+
+        <button
+          onclick={selectCustom}
+          class="w-full text-left px-4 py-3 rounded-lg border transition-colors {showCustomInput
+            ? 'bg-[var(--accent-primary)]/20 border-[var(--accent-primary)] text-[var(--text-primary)]'
+            : 'bg-[var(--bg-secondary)] border-[var(--border-color)] text-[var(--text-primary)] hover:border-[var(--accent-primary)]/50'}"
+        >
+          <div class="flex items-start gap-3">
+            <div
+              class="mt-0.5 w-5 h-5 rounded-full border-2 flex items-center justify-center {showCustomInput
+                ? 'border-[var(--accent-primary)] bg-[var(--accent-primary)]'
+                : 'border-[var(--text-secondary)]'}"
+            >
+              {#if showCustomInput}
+                <span class="text-white text-xs">x</span>
+              {/if}
+            </div>
+            <div class="flex-1">
+              <div class="font-medium">Other</div>
+              <div class="text-sm text-[var(--text-secondary)] mt-1">Provide a custom answer</div>
+            </div>
+          </div>
+        </button>
+      </div>
+
+      {#if showCustomInput}
+        <div class="mb-4">
+          <textarea
+            bind:value={customAnswer}
+            placeholder="Type your answer here..."
+            class="w-full px-4 py-3 bg-[var(--bg-secondary)] border border-[var(--border-color)] rounded-lg text-[var(--text-primary)] placeholder-[var(--text-secondary)] resize-none focus:outline-none focus:border-[var(--accent-primary)]"
+            rows="3"
+          ></textarea>
+        </div>
+      {/if}
+
+      <div class="flex gap-3">
+        <button
+          onclick={handleDismiss}
+          class="flex-1 px-4 py-2 bg-gray-500/20 hover:bg-gray-500/30 text-[var(--text-secondary)] rounded-lg transition-colors font-medium"
+        >
+          Dismiss
+        </button>
+        <button
+          onclick={handleSubmitAndReconnect}
+          disabled={!canSubmit()}
+          class="flex-1 px-4 py-2 bg-blue-500/20 hover:bg-blue-500/30 text-blue-400 rounded-lg transition-colors font-medium disabled:opacity-50 disabled:cursor-not-allowed"
+        >
+          Answer & Reconnect
+        </button>
+      </div>
+    </div>
+  </div>
+{/if}

src/lib/stores/claude.ts

@@ -21,6 +21,7 @@ export const claudeStore = {
   currentWorkingDirectory: conversationsStore.currentWorkingDirectory,
   terminalLines: conversationsStore.terminalLines,
   pendingPermission: conversationsStore.pendingPermission,
+  pendingQuestion: conversationsStore.pendingQuestion,
   isProcessing: conversationsStore.isProcessing,
   grantedTools: conversationsStore.grantedTools,
   pendingRetryMessage: conversationsStore.pendingRetryMessage,
@@ -49,6 +50,10 @@ export const claudeStore = {
   clearPermission: conversationsStore.clearPermission,
   requestPermissionForConversation: conversationsStore.requestPermissionForConversation,
   clearPermissionForConversation: conversationsStore.clearPermissionForConversation,
+  requestQuestion: conversationsStore.requestQuestion,
+  clearQuestion: conversationsStore.clearQuestion,
+  requestQuestionForConversation: conversationsStore.requestQuestionForConversation,
+  clearQuestionForConversation: conversationsStore.clearQuestionForConversation,
   grantTool: conversationsStore.grantTool,
   revokeAllTools: conversationsStore.revokeAllTools,
   isToolGranted: conversationsStore.isToolGranted,
@@ -89,6 +94,11 @@ export const hasPermissionPending = derived(
   ($conversation) => $conversation?.pendingPermission !== null
 );
 
+export const hasQuestionPending = derived(
+  claudeStore.activeConversation,
+  ($conversation) => $conversation?.pendingQuestion !== null
+);
+
 // Derived store to check if Claude is currently processing (can be interrupted)
 export const isClaudeProcessing = derived(
   [claudeStore.connectionStatus, characterState],

src/lib/stores/conversations.ts

@@ -1,5 +1,10 @@
 import { writable, derived, get } from "svelte/store";
-import type { TerminalLine, ConnectionStatus, PermissionRequest } from "$lib/types/messages";
+import type {
+  TerminalLine,
+  ConnectionStatus,
+  PermissionRequest,
+  UserQuestionEvent,
+} from "$lib/types/messages";
 import type { CharacterState } from "$lib/types/states";
 import { cleanupConversationTracking } from "$lib/tauri";
 import { characterState } from "$lib/stores/character";
@@ -15,6 +20,7 @@ export interface Conversation {
   isProcessing: boolean;
   grantedTools: Set<string>;
   pendingPermission: PermissionRequest | null;
+  pendingQuestion: UserQuestionEvent | null;
   createdAt: Date;
   lastActivityAt: Date;
 }
@@ -48,6 +54,7 @@ function createConversationsStore() {
       isProcessing: false,
       grantedTools: new Set(),
       pendingPermission: null,
+      pendingQuestion: null,
       createdAt: new Date(),
       lastActivityAt: new Date(),
     };
@@ -98,6 +105,7 @@ function createConversationsStore() {
     activeConversation,
     ($conv) => $conv?.pendingPermission || null
   );
+  const pendingQuestion = derived(activeConversation, ($conv) => $conv?.pendingQuestion || null);
 
   return {
     // Expose derived stores for compatibility
@@ -106,6 +114,7 @@ function createConversationsStore() {
     currentWorkingDirectory: { subscribe: currentWorkingDirectory.subscribe },
     terminalLines: { subscribe: terminalLines.subscribe },
     pendingPermission: { subscribe: pendingPermission.subscribe },
+    pendingQuestion: { subscribe: pendingQuestion.subscribe },
     isProcessing: { subscribe: isProcessing.subscribe },
     grantedTools: { subscribe: grantedTools.subscribe },
     pendingRetryMessage: { subscribe: pendingRetryMessage.subscribe },
@@ -199,6 +208,52 @@ function createConversationsStore() {
         return convs;
       });
     },
+    requestQuestion: (question: UserQuestionEvent) => {
+      const activeId = get(activeConversationId);
+      if (!activeId) return;
+
+      conversations.update((convs) => {
+        const conv = convs.get(activeId);
+        if (conv) {
+          conv.pendingQuestion = question;
+          conv.lastActivityAt = new Date();
+        }
+        return convs;
+      });
+    },
+    clearQuestion: () => {
+      const activeId = get(activeConversationId);
+      if (!activeId) return;
+
+      conversations.update((convs) => {
+        const conv = convs.get(activeId);
+        if (conv) {
+          conv.pendingQuestion = null;
+          conv.lastActivityAt = new Date();
+        }
+        return convs;
+      });
+    },
+    requestQuestionForConversation: (conversationId: string, question: UserQuestionEvent) => {
+      conversations.update((convs) => {
+        const conv = convs.get(conversationId);
+        if (conv) {
+          conv.pendingQuestion = question;
+          conv.lastActivityAt = new Date();
+        }
+        return convs;
+      });
+    },
+    clearQuestionForConversation: (conversationId: string) => {
+      conversations.update((convs) => {
+        const conv = convs.get(conversationId);
+        if (conv) {
+          conv.pendingQuestion = null;
+          conv.lastActivityAt = new Date();
+        }
+        return convs;
+      });
+    },
     setPendingRetryMessage: (message: string | null) => pendingRetryMessage.set(message),
 
     // Conversation management

src/lib/tauri.ts

@@ -6,7 +6,11 @@ import { characterState } from "$lib/stores/character";
 import { configStore } from "$lib/stores/config";
 import { initStatsListener, resetSessionStats } from "$lib/stores/stats";
 import { initAchievementsListener } from "$lib/stores/achievements";
-import type { ConnectionStatus, PermissionPromptEvent } from "$lib/types/messages";
+import type {
+  ConnectionStatus,
+  PermissionPromptEvent,
+  UserQuestionEvent,
+} from "$lib/types/messages";
 import type { CharacterState } from "$lib/types/states";
 import {
   initializeNotificationRules,
@@ -317,6 +321,25 @@ export async function initializeTauriListeners() {
     }
   });
   unlisteners.push(permissionUnlisten);
+
+  const questionUnlisten = await listen<UserQuestionEvent>("claude:question", (event) => {
+    const questionEvent = event.payload;
+
+    // Store question request for the specific conversation
+    if (questionEvent.conversation_id) {
+      claudeStore.requestQuestionForConversation(questionEvent.conversation_id, questionEvent);
+      claudeStore.addLineToConversation(
+        questionEvent.conversation_id,
+        "system",
+        `Question: ${questionEvent.question}`
+      );
+    } else {
+      // Fallback to active conversation if no conversation_id
+      claudeStore.requestQuestion(questionEvent);
+      claudeStore.addLine("system", `Question: ${questionEvent.question}`);
+    }
+  });
+  unlisteners.push(questionUnlisten);
 }
 
 export function cleanupTauriListeners() {

src/lib/types/messages.ts

@@ -126,4 +126,18 @@ export interface PermissionPromptEvent {
   conversation_id?: string;
 }
 
+export interface QuestionOption {
+  label: string;
+  description?: string;
+}
+
+export interface UserQuestionEvent {
+  id: string;
+  question: string;
+  header?: string;
+  options: QuestionOption[];
+  multi_select: boolean;
+  conversation_id?: string;
+}
+
 export type ConnectionStatus = "disconnected" | "connecting" | "connected" | "error";

src/routes/+page.svelte

@@ -14,6 +14,7 @@
   import StatusBar from "$lib/components/StatusBar.svelte";
   import AnimeGirl from "$lib/components/AnimeGirl.svelte";
   import PermissionModal from "$lib/components/PermissionModal.svelte";
+  import UserQuestionModal from "$lib/components/UserQuestionModal.svelte";
   import ConfigSidebar from "$lib/components/ConfigSidebar.svelte";
   import AchievementNotification from "$lib/components/AchievementNotification.svelte";
   import AchievementsPanel from "$lib/components/AchievementsPanel.svelte";
@@ -139,6 +140,7 @@
   </main>
 
   <PermissionModal />
+  <UserQuestionModal />
   <ConfigSidebar />
   <AchievementNotification />
   <AchievementsPanel