diff --git a/backend/server.js b/backend/server.js
index 50ca575..6a19746 100644
--- a/backend/server.js
+++ b/backend/server.js
@@ -129,6 +129,9 @@ function generateRequestId() {
 const server = createServer(app);
 const wss = new WebSocketServer({ server });
 
+// WebSocket heartbeat interval (30 seconds)
+const WS_HEARTBEAT_INTERVAL = 30000;
+
 // Scan directory for projects
 function scanProjects(basePath, depth = 0, maxDepth = 1) {
   const projects = [];
@@ -560,6 +563,20 @@ wss.on('connection', async (ws, req) => {
   const sessionId = uuidv4();
   console.log(`[${sessionId}] New WebSocket connection`);
 
+  // Track connection health
+  ws.isAlive = true;
+
+  // Heartbeat to keep connection alive through proxies
+  const heartbeatInterval = setInterval(() => {
+    if (ws.readyState === ws.OPEN) {
+      ws.ping();
+    }
+  }, WS_HEARTBEAT_INTERVAL);
+
+  ws.on('pong', () => {
+    ws.isAlive = true;
+  });
+
   // Authenticate WebSocket connection
   let wsUser = null;
   if (authConfig.app.authEnabled && sessionStore) {
@@ -1030,6 +1047,8 @@ wss.on('connection', async (ws, req) => {
 
   ws.on('close', () => {
     console.log(`[${sessionId}] WebSocket closed`);
+    clearInterval(heartbeatInterval);
+    clearInterval(cleanupInterval);
     if (claudeProcess) {
       claudeProcess.kill();
       sessions.delete(sessionId);
diff --git a/frontend/src/components/ChatPanel.jsx b/frontend/src/components/ChatPanel.jsx
index adce136..dd845eb 100644
--- a/frontend/src/components/ChatPanel.jsx
+++ b/frontend/src/components/ChatPanel.jsx
@@ -182,6 +182,7 @@ export const ChatPanel = memo(function ChatPanel({ sessionId }) {
         <MessageList
           messages={session.messages || []}
           isProcessing={session.isProcessing}
+          onSendMessage={handleSendMessage}
         />
       ) : (
         <WelcomeScreen session={session} onStart={start} />
diff --git a/frontend/src/components/MessageList.jsx b/frontend/src/components/MessageList.jsx
index 4aa7723..bf1db66 100644
--- a/frontend/src/components/MessageList.jsx
+++ b/frontend/src/components/MessageList.jsx
@@ -1,9 +1,10 @@
 import { useEffect, useRef, useState, useMemo, memo, useCallback } from 'react';
+import TextareaAutosize from 'react-textarea-autosize';
 import {
   User, Bot, Terminal, CheckCircle, AlertCircle, Info,
   FileText, Search, FolderSearch, Pencil, FilePlus, Globe,
   ChevronDown, ChevronRight, Play, ArrowDown,
-  ClipboardList, Brain, Paperclip, Image
+  ClipboardList, Brain, Paperclip, Image, HelpCircle, Zap, Command
 } from 'lucide-react';
 import ReactMarkdown from 'react-markdown';
 import remarkGfm from 'remark-gfm';
@@ -25,6 +26,50 @@ function parseSystemReminders(text) {
   return { content, reminders };
 }
 
+// Helper to extract thinking tags from content
+function parseThinking(text) {
+  if (!text || typeof text !== 'string') return { content: text || '', thinking: [] };
+
+  const thinking = [];
+  const thinkingRegex = /<thinking>([\s\S]*?)<\/thinking>/g;
+  let match;
+  while ((match = thinkingRegex.exec(text)) !== null) {
+    thinking.push(match[1].trim());
+  }
+
+  const content = text.replace(/<thinking>[\s\S]*?<\/thinking>/g, '').trim();
+  return { content, thinking };
+}
+
+// Collapsible thinking block component
+function ThinkingBlock({ thinking }) {
+  const [show, setShow] = useState(false);
+
+  if (!thinking || thinking.length === 0) return null;
+
+  return (
+    <div className="mb-3">
+      <button
+        onClick={() => setShow(!show)}
+        className="flex items-center gap-2 text-xs text-purple-400 hover:text-purple-300 transition-colors"
+      >
+        <Brain className="w-3.5 h-3.5" />
+        <span>Thinking</span>
+        {show ? <ChevronDown className="w-3 h-3" /> : <ChevronRight className="w-3 h-3" />}
+      </button>
+      {show && (
+        <div className="mt-2 p-3 bg-purple-900/10 border border-purple-500/20 rounded-lg">
+          {thinking.map((thought, idx) => (
+            <div key={idx} className="text-sm text-purple-300/80 italic whitespace-pre-wrap">
+              {thought}
+            </div>
+          ))}
+        </div>
+      )}
+    </div>
+  );
+}
+
 // Collapsible system hints component
 function SystemHints({ reminders, inline = false }) {
   const [show, setShow] = useState(false);
@@ -72,7 +117,7 @@ function SystemHints({ reminders, inline = false }) {
   );
 }
 
-export const MessageList = memo(function MessageList({ messages, isProcessing }) {
+export const MessageList = memo(function MessageList({ messages, isProcessing, onSendMessage }) {
   const containerRef = useRef(null);
   const messagesEndRef = useRef(null);
   const [showScrollButton, setShowScrollButton] = useState(false);
@@ -183,7 +228,7 @@ export const MessageList = memo(function MessageList({ messages, isProcessing })
         className="h-full overflow-y-auto p-4 space-y-4"
       >
         {processedMessages.map((message, index) => (
-          <Message key={`${message.type}-${message._originalIndex}-${message.timestamp || index}`} message={message} />
+          <Message key={`${message.type}-${message._originalIndex}-${message.timestamp || index}`} message={message} onSendMessage={onSendMessage} />
         ))}
 
         {/* Processing indicator */}
@@ -217,13 +262,19 @@ export const MessageList = memo(function MessageList({ messages, isProcessing })
   );
 });
 
-const Message = memo(function Message({ message }) {
+const Message = memo(function Message({ message, onSendMessage }) {
   const { type, content, tool, input, timestamp, toolUseId, attachments } = message;
 
-  // Memoize parsed system reminders for assistant messages
+  // Memoize parsed system reminders and thinking for assistant messages
   const parsedContent = useMemo(() => {
     if (type === 'assistant') {
-      return parseSystemReminders(content);
+      const withoutReminders = parseSystemReminders(content);
+      const withoutThinking = parseThinking(withoutReminders.content);
+      return {
+        content: withoutThinking.content,
+        reminders: withoutReminders.reminders,
+        thinking: withoutThinking.thinking,
+      };
     }
     return null;
   }, [type, content]);
@@ -269,7 +320,7 @@ const Message = memo(function Message({ message }) {
         );
 
       case 'assistant': {
-        const { content: cleanContent, reminders } = parsedContent;
+        const { content: cleanContent, reminders, thinking } = parsedContent;
         return (
           <div className="flex gap-3 message-enter">
             <div className="w-8 h-8 rounded-lg bg-orange-600 flex items-center justify-center flex-shrink-0">
@@ -278,6 +329,7 @@ const Message = memo(function Message({ message }) {
             <div className="max-w-[85%]">
               <div className="text-xs text-dark-500 mb-1">Claude</div>
               <div className="bg-dark-850 rounded-lg rounded-tl-none p-4 border border-dark-700 claude-message inline-block">
+                <ThinkingBlock thinking={thinking} />
                 <ReactMarkdown
                   remarkPlugins={[remarkGfm]}
                   components={{
@@ -318,7 +370,7 @@ const Message = memo(function Message({ message }) {
       case 'tool_use':
         // Note: ExitPlanMode approval now handled via PermissionDialog modal
         // Just show it as a normal tool use card in the message list
-        return <ToolUseCard tool={tool} input={input} result={message._pairedResult} />;
+        return <ToolUseCard tool={tool} input={input} result={message._pairedResult} onSendMessage={onSendMessage} />;
 
       case 'tool_result':
         return <ToolResultCard content={content} isSuccess={!message.isError} />;
@@ -456,16 +508,27 @@ const TOOL_CONFIG = {
     getSummary: (input) => input.task_id?.substring(0, 8) || 'task',
   },
   Skill: {
-    icon: Play,
+    icon: Zap,
     color: 'purple',
-    label: 'Using skill',
+    label: 'Launching skill',
     getSummary: (input) => input.skill || 'skill',
   },
   SlashCommand: {
-    icon: Terminal,
+    icon: Command,
     color: 'cyan',
     label: 'Running command',
-    getSummary: (input) => input.command || 'command',
+    getSummary: (input) => input.command?.split(' ')[0] || 'command',
+  },
+  AskUserQuestion: {
+    icon: HelpCircle,
+    color: 'yellow',
+    label: 'Asking question',
+    getSummary: (input) => {
+      const questions = input.questions || [];
+      if (questions.length === 1) return questions[0].header || 'question';
+      return `${questions.length} questions`;
+    },
+    isInteractive: true,
   },
   ExitPlanMode: {
     icon: ClipboardList,
@@ -541,8 +604,10 @@ const COLOR_CLASSES = {
 
 // Note: PlanApprovalCard removed - ExitPlanMode approval now handled via PermissionDialog modal
 
-const ToolUseCard = memo(function ToolUseCard({ tool, input, result }) {
+const ToolUseCard = memo(function ToolUseCard({ tool, input, result, onSendMessage }) {
   const [showResult, setShowResult] = useState(false);
+  const [selectedOptions, setSelectedOptions] = useState({});
+  const [customInput, setCustomInput] = useState('');
 
   const config = TOOL_CONFIG[tool] || {
     icon: Terminal,
@@ -864,6 +929,187 @@ const ToolUseCard = memo(function ToolUseCard({ tool, input, result }) {
       );
     }
 
+    if (tool === 'Skill') {
+      return (
+        <div className="space-y-2">
+          <div className="flex items-center gap-2">
+            <Zap className="w-4 h-4 text-purple-400" />
+            <span className="text-sm font-medium text-purple-400">{input.skill}</span>
+          </div>
+        </div>
+      );
+    }
+
+    if (tool === 'SlashCommand') {
+      return (
+        <div className="space-y-2">
+          <div className="flex items-center gap-2">
+            <Command className="w-4 h-4 text-cyan-400" />
+            <code className="text-sm text-cyan-400 bg-dark-800 px-2 py-0.5 rounded">{input.command}</code>
+          </div>
+        </div>
+      );
+    }
+
+    if (tool === 'AskUserQuestion') {
+      const questions = input.questions || [];
+      // Only consider it "answered" if there's a successful result (not an error)
+      const hasResult = result && !result.isError;
+
+      // Handle option selection
+      const handleOptionClick = (qIdx, optIdx, isMulti) => {
+        if (hasResult) return; // Already answered
+        setSelectedOptions(prev => {
+          const key = `q${qIdx}`;
+          if (isMulti) {
+            const current = prev[key] || [];
+            if (current.includes(optIdx)) {
+              return { ...prev, [key]: current.filter(i => i !== optIdx) };
+            }
+            return { ...prev, [key]: [...current, optIdx] };
+          }
+          return { ...prev, [key]: [optIdx] };
+        });
+      };
+
+      // Submit selected answers or custom input
+      const handleSubmit = () => {
+        if (!onSendMessage || hasResult) return;
+
+        // If custom input is provided, use that
+        if (customInput.trim()) {
+          onSendMessage(customInput.trim());
+          return;
+        }
+
+        // Otherwise use selected options
+        const answers = questions.map((q, qIdx) => {
+          const selected = selectedOptions[`q${qIdx}`] || [];
+          const labels = selected.map(idx => q.options[idx]?.label).filter(Boolean);
+          return labels.join(', ') || '';
+        }).filter(Boolean);
+
+        if (answers.length > 0) {
+          onSendMessage(answers.join('\n'));
+        }
+      };
+
+      const isOptionSelected = (qIdx, optIdx) => {
+        return (selectedOptions[`q${qIdx}`] || []).includes(optIdx);
+      };
+
+      const hasSelection = Object.values(selectedOptions).some(arr => arr.length > 0);
+      const canSubmit = hasSelection || customInput.trim();
+
+      return (
+        <div className="space-y-5">
+          {questions.map((q, qIdx) => (
+            <div key={qIdx} className="space-y-3">
+              {/* Question header */}
+              <div className="flex items-center gap-2">
+                <span className="px-2.5 py-1 bg-yellow-500/20 text-yellow-400 text-xs font-medium rounded-md">
+                  {q.header}
+                </span>
+                {q.multiSelect && (
+                  <span className="text-xs text-dark-500">(select multiple)</span>
+                )}
+              </div>
+
+              {/* Question text */}
+              <p className="text-sm text-dark-200 leading-relaxed">{q.question}</p>
+
+              {/* Options as grid for better layout */}
+              <div className="grid gap-2">
+                {q.options?.map((opt, optIdx) => {
+                  const isSelected = isOptionSelected(qIdx, optIdx);
+                  return (
+                    <button
+                      key={optIdx}
+                      onClick={() => handleOptionClick(qIdx, optIdx, q.multiSelect)}
+                      disabled={hasResult}
+                      className={`w-full flex items-start gap-3 p-3 rounded-lg border text-left
+                        transition-all duration-200 ease-out
+                        ${hasResult
+                          ? 'bg-dark-800/30 border-dark-700 opacity-60 cursor-not-allowed'
+                          : isSelected
+                            ? 'bg-yellow-500/20 border-yellow-500/50 shadow-lg shadow-yellow-500/10 scale-[1.01]'
+                            : 'bg-dark-800/50 border-dark-700 hover:border-yellow-500/30 hover:bg-dark-800 hover:scale-[1.005]'
+                        }`}
+                    >
+                      <div className="mt-0.5 transition-transform duration-200">
+                        {q.multiSelect ? (
+                          <div className={`w-5 h-5 rounded border-2 flex items-center justify-center transition-all duration-200 ${
+                            isSelected ? 'border-yellow-500 bg-yellow-500 scale-110' : 'border-dark-500 bg-dark-700'
+                          }`}>
+                            {isSelected && <CheckCircle className="w-3.5 h-3.5 text-dark-900" />}
+                          </div>
+                        ) : (
+                          <div className={`w-5 h-5 rounded-full border-2 flex items-center justify-center transition-all duration-200 ${
+                            isSelected ? 'border-yellow-500 bg-yellow-500 scale-110' : 'border-dark-500 bg-dark-700'
+                          }`}>
+                            {isSelected && <div className="w-2.5 h-2.5 rounded-full bg-dark-900" />}
+                          </div>
+                        )}
+                      </div>
+                      <div className="flex-1 min-w-0">
+                        <div className={`text-sm font-medium transition-colors duration-200 ${isSelected ? 'text-yellow-300' : 'text-dark-200'}`}>
+                          {opt.label}
+                        </div>
+                        {opt.description && (
+                          <div className="text-xs text-dark-500 mt-1 leading-relaxed">{opt.description}</div>
+                        )}
+                      </div>
+                    </button>
+                  );
+                })}
+              </div>
+            </div>
+          ))}
+
+          {/* Custom input + Submit section */}
+          {!hasResult && onSendMessage && (
+            <div className="space-y-3 pt-3 border-t border-dark-700">
+              {/* Custom input field */}
+              <div className="space-y-2">
+                <label className="text-xs text-dark-500 font-medium">Or type a custom response:</label>
+                <TextareaAutosize
+                  value={customInput}
+                  onChange={(e) => setCustomInput(e.target.value)}
+                  placeholder="Enter your own answer..."
+                  minRows={2}
+                  maxRows={6}
+                  className="w-full px-3 py-2 bg-dark-800 border border-dark-700 rounded-lg text-sm text-dark-200
+                    placeholder-dark-500 resize-none
+                    focus:outline-none focus:border-yellow-500/50 focus:ring-1 focus:ring-yellow-500/20
+                    transition-all duration-200"
+                />
+              </div>
+
+              {/* Submit button */}
+              <button
+                onClick={handleSubmit}
+                disabled={!canSubmit}
+                className={`w-full py-2.5 rounded-lg text-sm font-medium transition-all duration-200 ${
+                  canSubmit
+                    ? 'bg-yellow-500 text-dark-900 hover:bg-yellow-400 shadow-lg shadow-yellow-500/20 hover:shadow-yellow-500/30'
+                    : 'bg-dark-700 text-dark-500 cursor-not-allowed'
+                }`}
+              >
+                Submit Answer
+              </button>
+            </div>
+          )}
+
+          {hasResult && (
+            <div className="flex items-center gap-2 pt-3 border-t border-dark-700 text-sm text-green-400">
+              <CheckCircle className="w-4 h-4" />
+              <span>Response submitted</span>
+            </div>
+          )}
+        </div>
+      );
+    }
+
     // Default JSON view
     return (
       <SyntaxHighlighter
@@ -886,8 +1132,13 @@ const ToolUseCard = memo(function ToolUseCard({ tool, input, result }) {
     resultData.contentStr.startsWith('[')
   );
 
+  // Interactive tools like AskUserQuestion need more space
+  const isInteractiveTool = config.isInteractive;
+  const cardWidthClass = isInteractiveTool ? 'w-full max-w-2xl' : 'inline-block max-w-[85%]';
+  const contentHeightClass = isInteractiveTool ? '' : 'max-h-48 overflow-y-auto';
+
   return (
-    <div className={`ml-11 message-enter rounded-lg border ${colors.border} ${colors.bg} overflow-hidden transition-all duration-200 hover:shadow-lg ${colors.glow} inline-block max-w-[85%]`}>
+    <div className={`ml-11 message-enter rounded-lg border ${colors.border} ${colors.bg} overflow-hidden transition-all duration-200 hover:shadow-lg ${colors.glow} ${cardWidthClass}`}>
       {/* Header */}
       <div className="flex items-center gap-3 p-2.5">
         {/* Icon */}
@@ -902,8 +1153,8 @@ const ToolUseCard = memo(function ToolUseCard({ tool, input, result }) {
             <span className="text-dark-600">•</span>
             <code className="text-xs text-dark-300 truncate">{summary}</code>
 
-            {/* Result badge */}
-            {resultData && (
+            {/* Result badge - hide for interactive tools since they handle their own state */}
+            {resultData && !isInteractiveTool && (
               <>
                 <span className="text-dark-600">•</span>
                 <span className={`inline-flex items-center gap-1 text-xs ${resultData.isSuccess ? 'text-green-400' : 'text-red-400'}`}>
@@ -920,13 +1171,13 @@ const ToolUseCard = memo(function ToolUseCard({ tool, input, result }) {
         </div>
       </div>
 
-      {/* Content - always visible with max height and scroll */}
-      <div className="border-t border-dark-700/50 p-3 bg-dark-900/50 max-h-48 overflow-y-auto overflow-x-auto">
+      {/* Content - interactive tools get full height, others are capped */}
+      <div className={`border-t border-dark-700/50 p-3 bg-dark-900/50 overflow-x-auto ${contentHeightClass}`}>
         {renderSpecialInput()}
       </div>
 
-      {/* Collapsible Result Section */}
-      {resultData && (
+      {/* Collapsible Result Section - hide for interactive tools */}
+      {resultData && !isInteractiveTool && (
         <div className="border-t border-dark-700/50">
           <button
             onClick={() => setShowResult(!showResult)}
diff --git a/frontend/src/hooks/useClaudeSession.js b/frontend/src/hooks/useClaudeSession.js
index ee6dfcf..33d072c 100644
--- a/frontend/src/hooks/useClaudeSession.js
+++ b/frontend/src/hooks/useClaudeSession.js
@@ -9,6 +9,11 @@ function getWsUrl() {
 
 const MAX_FILE_SIZE = 10 * 1024 * 1024; // 10MB
 
+// Reconnect configuration
+const RECONNECT_DELAY_BASE = 1000; // 1 second
+const RECONNECT_DELAY_MAX = 30000; // 30 seconds
+const RECONNECT_MAX_ATTEMPTS = 10;
+
 export function useClaudeSession() {
   const [connected, setConnected] = useState(false);
   const [sessionActive, setSessionActive] = useState(false);
@@ -50,6 +55,9 @@ export function useClaudeSession() {
 
   const wsRef = useRef(null);
   const currentAssistantMessage = useRef(null);
+  const reconnectAttempts = useRef(0);
+  const reconnectTimeout = useRef(null);
+  const intentionalClose = useRef(false);
 
   const connect = useCallback(() => {
     if (wsRef.current?.readyState === WebSocket.OPEN) return;
@@ -61,13 +69,34 @@ export function useClaudeSession() {
       console.log('WebSocket connected');
       setConnected(true);
       setError(null);
+      reconnectAttempts.current = 0; // Reset on successful connection
     };
 
-    ws.onclose = () => {
-      console.log('WebSocket disconnected');
+    ws.onclose = (event) => {
+      console.log('WebSocket disconnected', { code: event.code, reason: event.reason, wasClean: event.wasClean });
       setConnected(false);
       setSessionActive(false);
       setIsProcessing(false);
+
+      // Attempt reconnect unless it was intentional or auth failure
+      if (!intentionalClose.current && event.code !== 1008) {
+        if (reconnectAttempts.current < RECONNECT_MAX_ATTEMPTS) {
+          const delay = Math.min(
+            RECONNECT_DELAY_BASE * Math.pow(2, reconnectAttempts.current),
+            RECONNECT_DELAY_MAX
+          );
+          reconnectAttempts.current++;
+          console.log(`Reconnecting in ${delay}ms (attempt ${reconnectAttempts.current}/${RECONNECT_MAX_ATTEMPTS})`);
+
+          reconnectTimeout.current = setTimeout(() => {
+            console.log('Attempting reconnect...');
+            connect();
+          }, delay);
+        } else {
+          console.log('Max reconnect attempts reached');
+          setError('Connection lost. Please refresh the page.');
+        }
+      }
     };
 
     ws.onerror = (err) => {
@@ -543,8 +572,13 @@ export function useClaudeSession() {
 
   // Auto-connect on mount
   useEffect(() => {
+    intentionalClose.current = false;
     connect();
     return () => {
+      intentionalClose.current = true;
+      if (reconnectTimeout.current) {
+        clearTimeout(reconnectTimeout.current);
+      }
       wsRef.current?.close();
     };
   }, [connect]);