diff --git a/server/modules/websocket/services/shell-websocket.service.ts b/server/modules/websocket/services/shell-websocket.service.ts
index b8f34ae8..a29959be 100644
--- a/server/modules/websocket/services/shell-websocket.service.ts
+++ b/server/modules/websocket/services/shell-websocket.service.ts
@@ -18,6 +18,7 @@ type ShellIncomingMessage = {
   provider?: string;
   initialCommand?: string;
   isPlainShell?: boolean;
+  forceRestart?: boolean;
 };
 
 type PtySessionEntry = {
@@ -180,6 +181,7 @@ export function handleShellConnection(
         const hasSession = readBoolean(data.hasSession);
         const provider = readString(data.provider, 'claude');
         const initialCommand = readString(data.initialCommand);
+        const forceRestart = readBoolean(data.forceRestart);
         const isPlainShell =
           readBoolean(data.isPlainShell) ||
           (!!initialCommand && !hasSession) ||
@@ -200,7 +202,7 @@ export function handleShellConnection(
             : '';
         ptySessionKey = `${projectPath}_${sessionId ?? 'default'}${commandSuffix}`;
 
-        if (isLoginCommand) {
+        if (isLoginCommand || forceRestart) {
           const oldSession = ptySessionsMap.get(ptySessionKey);
           if (oldSession) {
             if (oldSession.timeoutId) {
@@ -211,7 +213,8 @@ export function handleShellConnection(
           }
         }
 
-        const existingSession = isLoginCommand ? null : ptySessionsMap.get(ptySessionKey);
+        const existingSession =
+          isLoginCommand || forceRestart ? null : ptySessionsMap.get(ptySessionKey);
         if (existingSession) {
           shellProcess = existingSession.pty;
           if (existingSession.timeoutId) {
@@ -368,6 +371,10 @@ export function handleShellConnection(
           }
 
           const session = ptySessionsMap.get(ptySessionKey);
+          if (session && session.pty !== shellProcess) {
+            return;
+          }
+
           if (session && session.ws && session.ws.readyState === WebSocket.OPEN) {
             session.ws.send(
               JSON.stringify({
@@ -451,6 +458,10 @@ export function handleShellConnection(
 
     session.ws = null;
     session.timeoutId = setTimeout(() => {
+      if (ptySessionsMap.get(ptySessionKey as string) !== session) {
+        return;
+      }
+
       session.pty.kill();
       ptySessionsMap.delete(ptySessionKey as string);
     }, PTY_SESSION_TIMEOUT);
diff --git a/src/components/shell/hooks/useShellConnection.ts b/src/components/shell/hooks/useShellConnection.ts
index 7babed15..918ed76c 100644
--- a/src/components/shell/hooks/useShellConnection.ts
+++ b/src/components/shell/hooks/useShellConnection.ts
@@ -2,6 +2,7 @@ import { useCallback, useEffect, useRef, useState } from 'react';
 import type { MutableRefObject } from 'react';
 import type { FitAddon } from '@xterm/addon-fit';
 import type { Terminal } from '@xterm/xterm';
+
 import type { Project, ProjectSession } from '../../../types/app';
 import { TERMINAL_INIT_DELAY_MS } from '../constants/constants';
 import { getShellWebSocketUrl, parseShellMessage, sendSocketMessage } from '../utils/socket';
@@ -31,8 +32,8 @@ type UseShellConnectionResult = {
   isConnected: boolean;
   isConnecting: boolean;
   closeSocket: () => void;
-  connectToShell: () => void;
-  disconnectFromShell: () => void;
+  connectToShell: (options?: { forceRestart?: boolean }) => void;
+  disconnectFromShell: (options?: { suppressAutoConnect?: boolean }) => void;
 };
 
 export function useShellConnection({
@@ -54,6 +55,8 @@ export function useShellConnection({
   const [isConnected, setIsConnected] = useState(false);
   const [isConnecting, setIsConnecting] = useState(false);
   const connectingRef = useRef(false);
+  const forceRestartOnInitRef = useRef(false);
+  const suppressAutoConnectRef = useRef(false);
 
   const handleProcessCompletion = useCallback(
     (output: string) => {
@@ -141,6 +144,8 @@ export function useShellConnection({
             }
 
             currentFitAddon.fit();
+            const forceRestart = forceRestartOnInitRef.current;
+            forceRestartOnInitRef.current = false;
 
             sendSocketMessage(socket, {
               type: 'init',
@@ -152,6 +157,7 @@ export function useShellConnection({
               rows: currentTerminal.rows,
               initialCommand: initialCommandRef.current,
               isPlainShell: isPlainShellRef.current,
+              forceRestart,
             });
           }, TERMINAL_INIT_DELAY_MS);
         };
@@ -177,6 +183,7 @@ export function useShellConnection({
         setIsConnected(false);
         setIsConnecting(false);
         connectingRef.current = false;
+        forceRestartOnInitRef.current = false;
       }
     },
     [
@@ -195,27 +202,40 @@ export function useShellConnection({
     ],
   );
 
-  const connectToShell = useCallback(() => {
+  const connectToShell = useCallback((options?: { forceRestart?: boolean }) => {
     if (!isInitialized || isConnected || isConnecting || connectingRef.current) {
       return;
     }
 
+    forceRestartOnInitRef.current = Boolean(options?.forceRestart);
+    suppressAutoConnectRef.current = false;
     connectingRef.current = true;
     setIsConnecting(true);
     connectWebSocket(true);
   }, [connectWebSocket, isConnected, isConnecting, isInitialized]);
 
-  const disconnectFromShell = useCallback(() => {
+  const disconnectFromShell = useCallback((options?: { suppressAutoConnect?: boolean }) => {
+    if (options?.suppressAutoConnect) {
+      suppressAutoConnectRef.current = true;
+    }
+
     closeSocket();
     clearTerminalScreen();
     setIsConnected(false);
     setIsConnecting(false);
     connectingRef.current = false;
+    forceRestartOnInitRef.current = false;
     setAuthUrl('');
   }, [clearTerminalScreen, closeSocket, setAuthUrl]);
 
   useEffect(() => {
-    if (!autoConnect || !isInitialized || isConnecting || isConnected) {
+    if (
+      !autoConnect ||
+      suppressAutoConnectRef.current ||
+      !isInitialized ||
+      isConnecting ||
+      isConnected
+    ) {
       return;
     }
 
diff --git a/src/components/shell/types/types.ts b/src/components/shell/types/types.ts
index 14df2ea7..72a19785 100644
--- a/src/components/shell/types/types.ts
+++ b/src/components/shell/types/types.ts
@@ -1,6 +1,7 @@
 import type { MutableRefObject, RefObject } from 'react';
 import type { FitAddon } from '@xterm/addon-fit';
 import type { Terminal } from '@xterm/xterm';
+
 import type { Project, ProjectSession } from '../../../types/app';
 
 export type AuthCopyStatus = 'idle' | 'copied' | 'failed';
@@ -15,6 +16,7 @@ export type ShellInitMessage = {
   rows: number;
   initialCommand: string | null | undefined;
   isPlainShell: boolean;
+  forceRestart?: boolean;
 };
 
 export type ShellResizeMessage = {
@@ -69,8 +71,8 @@ export type UseShellRuntimeResult = {
   isConnecting: boolean;
   authUrl: string;
   authUrlVersion: number;
-  connectToShell: () => void;
-  disconnectFromShell: () => void;
+  connectToShell: (options?: { forceRestart?: boolean }) => void;
+  disconnectFromShell: (options?: { suppressAutoConnect?: boolean }) => void;
   openAuthUrlInBrowser: (url?: string) => boolean;
   copyAuthUrlToClipboard: (url?: string) => Promise<boolean>;
 };
diff --git a/src/components/shell/view/Shell.tsx b/src/components/shell/view/Shell.tsx
index a31a3319..575b0ac3 100644
--- a/src/components/shell/view/Shell.tsx
+++ b/src/components/shell/view/Shell.tsx
@@ -1,5 +1,6 @@
 import { useCallback, useEffect, useMemo, useRef, useState } from 'react';
 import { useTranslation } from 'react-i18next';
+
 import '@xterm/xterm/css/xterm.css';
 import type { Project, ProjectSession } from '../../../types/app';
 import {
@@ -13,6 +14,7 @@ import {
 import { useShellRuntime } from '../hooks/useShellRuntime';
 import { sendSocketMessage } from '../utils/socket';
 import { getSessionDisplayName } from '../utils/auth';
+
 import ShellConnectionOverlay from './subcomponents/ShellConnectionOverlay';
 import ShellEmptyState from './subcomponents/ShellEmptyState';
 import ShellHeader from './subcomponents/ShellHeader';
@@ -46,6 +48,8 @@ export default function Shell({
   const [isRestarting, setIsRestarting] = useState(false);
   const [cliPromptOptions, setCliPromptOptions] = useState<CliPromptOption[] | null>(null);
   const promptCheckTimer = useRef<ReturnType<typeof setTimeout> | null>(null);
+  const restartTimerRef = useRef<ReturnType<typeof setTimeout> | null>(null);
+  const restartAfterInitRef = useRef(false);
   const onOutputRef = useRef<(() => void) | null>(null);
 
   const {
@@ -140,6 +144,7 @@ export default function Shell({
   useEffect(() => {
     return () => {
       if (promptCheckTimer.current) clearTimeout(promptCheckTimer.current);
+      if (restartTimerRef.current) clearTimeout(restartTimerRef.current);
     };
   }, []);
 
@@ -190,12 +195,42 @@ export default function Shell({
   );
 
   const handleRestartShell = useCallback(() => {
+    restartAfterInitRef.current = true;
     setIsRestarting(true);
-    window.setTimeout(() => {
+    if (restartTimerRef.current) {
+      clearTimeout(restartTimerRef.current);
+    }
+    restartTimerRef.current = setTimeout(() => {
       setIsRestarting(false);
+      restartTimerRef.current = null;
     }, SHELL_RESTART_DELAY_MS);
   }, []);
 
+  const handleDisconnectShell = useCallback(() => {
+    restartAfterInitRef.current = false;
+    if (restartTimerRef.current) {
+      clearTimeout(restartTimerRef.current);
+      restartTimerRef.current = null;
+    }
+    setIsRestarting(false);
+    disconnectFromShell({ suppressAutoConnect: true });
+  }, [disconnectFromShell]);
+
+  useEffect(() => {
+    if (
+      !restartAfterInitRef.current ||
+      isRestarting ||
+      !isInitialized ||
+      isConnected ||
+      isConnecting
+    ) {
+      return;
+    }
+
+    restartAfterInitRef.current = false;
+    connectToShell({ forceRestart: true });
+  }, [connectToShell, isConnected, isConnecting, isInitialized, isRestarting]);
+
   if (!selectedProject) {
     return (
       <ShellEmptyState
@@ -254,7 +289,7 @@ export default function Shell({
         isRestarting={isRestarting}
         hasSession={Boolean(selectedSession)}
         sessionDisplayNameShort={sessionDisplayNameShort}
-        onDisconnect={disconnectFromShell}
+        onDisconnect={handleDisconnectShell}
         onRestart={handleRestartShell}
         statusNewSessionText={t('shell.status.newSession')}
         statusInitializingText={t('shell.status.initializing')}
@@ -263,7 +298,7 @@ export default function Shell({
         disconnectTitle={t('shell.actions.disconnectTitle')}
         restartLabel={t('shell.actions.restart')}
         restartTitle={t('shell.actions.restartTitle')}
-        disableRestart={isRestarting || isConnected}
+        disableRestart={isRestarting || !isInitialized}
       />
 
       <div className="relative flex-1 overflow-hidden p-2">
@@ -281,7 +316,7 @@ export default function Shell({
             connectLabel={t('shell.actions.connect')}
             connectTitle={t('shell.actions.connectTitle')}
             connectingLabel={t('shell.connecting')}
-            onConnect={connectToShell}
+            onConnect={handleRestartShell}
           />
         )}
 
diff --git a/src/components/shell/view/subcomponents/ShellConnectionOverlay.tsx b/src/components/shell/view/subcomponents/ShellConnectionOverlay.tsx
index 9ed94380..b0bacb9e 100644
--- a/src/components/shell/view/subcomponents/ShellConnectionOverlay.tsx
+++ b/src/components/shell/view/subcomponents/ShellConnectionOverlay.tsx
@@ -1,3 +1,5 @@
+import { Loader2, RotateCcw } from 'lucide-react';
+
 type ShellConnectionOverlayProps = {
   mode: 'loading' | 'connect' | 'connecting';
   description: string;
@@ -19,40 +21,42 @@ export default function ShellConnectionOverlay({
 }: ShellConnectionOverlayProps) {
   if (mode === 'loading') {
     return (
-      <div className="absolute inset-0 flex items-center justify-center bg-gray-900 bg-opacity-90">
-        <div className="text-white">{loadingLabel}</div>
+      <div className="absolute inset-0 z-20 flex items-center justify-center bg-gray-950/90">
+        <div className="inline-flex items-center gap-2 text-sm font-medium text-gray-100">
+          <Loader2 className="h-4 w-4 animate-spin text-blue-300" aria-hidden="true" />
+          <span>{loadingLabel}</span>
+        </div>
       </div>
     );
   }
 
   if (mode === 'connect') {
     return (
-      <div className="absolute inset-0 flex items-center justify-center bg-gray-900 bg-opacity-90 p-4">
-        <div className="w-full max-w-sm text-center">
+      <div className="absolute inset-0 z-20 flex items-center justify-center bg-gray-950/90 p-6">
+        <div className="flex w-full max-w-md flex-col items-center gap-3 text-center">
           <button
+            type="button"
             onClick={onConnect}
-            className="flex w-full items-center justify-center space-x-2 rounded-lg bg-green-600 px-6 py-3 text-base font-medium text-white transition-colors hover:bg-green-700 sm:w-auto"
+            className="pointer-events-auto inline-flex min-h-12 w-full max-w-xs cursor-pointer items-center justify-center gap-2 rounded-md bg-emerald-600 px-5 py-3 text-base font-semibold text-white shadow-lg shadow-emerald-950/30 transition-colors hover:bg-emerald-500 focus:outline-none focus:ring-2 focus:ring-emerald-300 focus:ring-offset-2 focus:ring-offset-gray-950 active:bg-emerald-700"
             title={connectTitle}
           >
-            <svg className="h-5 w-5" fill="none" stroke="currentColor" viewBox="0 0 24 24">
-              <path strokeLinecap="round" strokeLinejoin="round" strokeWidth={2} d="M13 10V3L4 14h7v7l9-11h-7z" />
-            </svg>
-            <span>{connectLabel}</span>
+            <RotateCcw className="h-4 w-4" aria-hidden="true" />
+            <span className="min-w-0 truncate">{connectLabel}</span>
           </button>
-          <p className="mt-3 px-2 text-sm text-gray-400">{description}</p>
+          <p className="max-w-md break-words px-2 text-sm leading-6 text-gray-300">{description}</p>
         </div>
       </div>
     );
   }
 
   return (
-    <div className="absolute inset-0 flex items-center justify-center bg-gray-900 bg-opacity-90 p-4">
-      <div className="w-full max-w-sm text-center">
-        <div className="flex items-center justify-center space-x-3 text-yellow-400">
-          <div className="h-6 w-6 animate-spin rounded-full border-2 border-yellow-400 border-t-transparent"></div>
+    <div className="absolute inset-0 z-20 flex items-center justify-center bg-gray-950/90 p-6">
+      <div className="flex w-full max-w-md flex-col items-center gap-3 text-center">
+        <div className="flex items-center justify-center gap-3 text-yellow-300">
+          <Loader2 className="h-5 w-5 animate-spin" aria-hidden="true" />
           <span className="text-base font-medium">{connectingLabel}</span>
         </div>
-        <p className="mt-3 px-2 text-sm text-gray-400">{description}</p>
+        <p className="max-w-md break-words px-2 text-sm leading-6 text-gray-300">{description}</p>
       </div>
     </div>
   );
diff --git a/src/components/shell/view/subcomponents/ShellHeader.tsx b/src/components/shell/view/subcomponents/ShellHeader.tsx
index 0495bc9a..187fd2df 100644
--- a/src/components/shell/view/subcomponents/ShellHeader.tsx
+++ b/src/components/shell/view/subcomponents/ShellHeader.tsx
@@ -1,3 +1,5 @@
+import { RotateCcw, X } from 'lucide-react';
+
 type ShellHeaderProps = {
   isConnected: boolean;
   isInitialized: boolean;
@@ -50,34 +52,27 @@ export default function ShellHeader({
           {isRestarting && <span className="text-xs text-blue-400">{statusRestartingText}</span>}
         </div>
 
-        <div className="flex items-center space-x-3">
+        <div className="flex items-center gap-2">
           {isConnected && (
             <button
+              type="button"
               onClick={onDisconnect}
-              className="flex items-center space-x-1 rounded bg-red-600 px-3 py-1 text-xs text-white hover:bg-red-700"
+              className="inline-flex h-8 items-center gap-1.5 rounded-md bg-red-600 px-3 text-xs font-medium text-white transition-colors hover:bg-red-700 focus:outline-none focus:ring-2 focus:ring-red-400/70 focus:ring-offset-2 focus:ring-offset-gray-800"
               title={disconnectTitle}
             >
-              <svg className="h-3 w-3" fill="none" stroke="currentColor" viewBox="0 0 24 24">
-                <path strokeLinecap="round" strokeLinejoin="round" strokeWidth={2} d="M6 18L18 6M6 6l12 12" />
-              </svg>
+              <X className="h-3.5 w-3.5" aria-hidden="true" />
               <span>{disconnectLabel}</span>
             </button>
           )}
 
           <button
+            type="button"
             onClick={onRestart}
             disabled={disableRestart}
-            className="flex items-center space-x-1 text-xs text-gray-400 hover:text-white disabled:cursor-not-allowed disabled:opacity-50"
+            className="inline-flex h-8 items-center gap-1.5 rounded-md border border-gray-600/80 bg-gray-700/70 px-3 text-xs font-medium text-gray-100 transition-colors hover:border-blue-400/70 hover:bg-blue-600/80 hover:text-white focus:outline-none focus:ring-2 focus:ring-blue-400/70 focus:ring-offset-2 focus:ring-offset-gray-800 disabled:cursor-not-allowed disabled:border-transparent disabled:bg-transparent disabled:text-gray-500 disabled:opacity-60"
             title={restartTitle}
           >
-            <svg className="h-3 w-3" fill="none" stroke="currentColor" viewBox="0 0 24 24">
-              <path
-                strokeLinecap="round"
-                strokeLinejoin="round"
-                strokeWidth={2}
-                d="M4 4v5h.582m15.356 2A8.001 8.001 0 004.582 9m0 0H9m11 11v-5h-.581m0 0a8.003 8.003 0 01-15.357-2m15.357 2H15"
-              />
-            </svg>
+            <RotateCcw className={`h-3.5 w-3.5 ${isRestarting ? 'animate-spin' : ''}`} aria-hidden="true" />
             <span>{restartLabel}</span>
           </button>
         </div>
diff --git a/src/i18n/locales/en/chat.json b/src/i18n/locales/en/chat.json
index 2f5af581..eac18ade 100644
--- a/src/i18n/locales/en/chat.json
+++ b/src/i18n/locales/en/chat.json
@@ -229,7 +229,7 @@
       "disconnect": "Disconnect",
       "disconnectTitle": "Disconnect from shell",
       "restart": "Restart",
-      "restartTitle": "Restart Shell (disconnect first)",
+      "restartTitle": "Restart Shell",
       "connect": "Continue in Shell",
       "connectTitle": "Connect to shell"
     },