diff --git a/src/cliproxy/auth/auth-types.ts b/src/cliproxy/auth/auth-types.ts
index 91ee2692..234a00ba 100644
--- a/src/cliproxy/auth/auth-types.ts
+++ b/src/cliproxy/auth/auth-types.ts
@@ -221,4 +221,6 @@ export interface OAuthOptions {
   import?: boolean;
   /** Enable paste-callback mode: show auth URL and prompt for callback paste */
   pasteCallback?: boolean;
+  /** If true, use port-forwarding mode (skip interactive prompt in headless) */
+  portForward?: boolean;
 }
diff --git a/src/cliproxy/auth/oauth-handler.ts b/src/cliproxy/auth/oauth-handler.ts
index c9b7de05..f8fe82b6 100644
--- a/src/cliproxy/auth/oauth-handler.ts
+++ b/src/cliproxy/auth/oauth-handler.ts
@@ -58,6 +58,55 @@ async function promptAddAccount(): Promise<boolean> {
   });
 }
 
+/**
+ * Prompt user to choose OAuth mode for headless environment
+ * Returns 'paste' for paste-callback mode or 'forward' for port-forwarding
+ */
+async function promptOAuthModeChoice(callbackPort: number | null): Promise<'paste' | 'forward'> {
+  const readline = await import('readline');
+  const rl = readline.createInterface({
+    input: process.stdin,
+    output: process.stdout,
+  });
+
+  console.log('');
+  console.log(info('Headless environment detected (SSH session)'));
+  console.log('    OAuth requires choosing a mode:');
+  console.log('');
+  console.log('    [1] Paste-callback (recommended for VPS)');
+  console.log('        Open URL in any browser, paste redirect URL back');
+  console.log('');
+  console.log('    [2] Port forwarding (advanced)');
+  if (callbackPort) {
+    console.log(`        Requires: ssh -L ${callbackPort}:localhost:${callbackPort} <USER>@<HOST>`);
+  } else {
+    console.log('        Requires SSH tunnel to callback port');
+  }
+  console.log('');
+
+  return new Promise<'paste' | 'forward'>((resolve) => {
+    let resolved = false;
+
+    // Handle Ctrl+C gracefully
+    rl.on('close', () => {
+      if (!resolved) {
+        resolved = true;
+        resolve('paste'); // Safe default on cancel
+      }
+    });
+
+    rl.question('[?] Which mode? (1/2): ', (answer) => {
+      const choice = answer.trim();
+      if (choice !== '1' && choice !== '2') {
+        console.log(info('Invalid choice, using paste-callback mode'));
+      }
+      resolved = true;
+      rl.close();
+      resolve(choice === '2' ? 'forward' : 'paste');
+    });
+  });
+}
+
 /**
  * Prompt user for account nickname (required for kiro/ghcp)
  * Returns null if user cancels
@@ -389,6 +438,22 @@ export async function triggerOAuth(
   const headless = options.headless ?? isHeadlessEnvironment();
   const isDeviceCodeFlow = callbackPort === null;
 
+  // Interactive mode selection for headless environments
+  // Skip if explicit mode flag provided or device code flow (no callback needed)
+  if (headless && !options.pasteCallback && !options.portForward && !isDeviceCodeFlow) {
+    // Non-interactive environment (piped input) - default to paste mode
+    if (!process.stdin.isTTY) {
+      const tokenDir = getProviderTokenDir(provider);
+      return handlePasteCallbackMode(provider, oauthConfig, verbose, tokenDir, nickname);
+    }
+    const mode = await promptOAuthModeChoice(callbackPort);
+    if (mode === 'paste') {
+      const tokenDir = getProviderTokenDir(provider);
+      return handlePasteCallbackMode(provider, oauthConfig, verbose, tokenDir, nickname);
+    }
+    // mode === 'forward' continues to existing port-forwarding flow below
+  }
+
   if (existingAccounts.length > 0 && !add) {
     console.log('');
     console.log(
diff --git a/src/cliproxy/cliproxy-executor.ts b/src/cliproxy/cliproxy-executor.ts
index a9e0cc73..6b924a35 100644
--- a/src/cliproxy/cliproxy-executor.ts
+++ b/src/cliproxy/cliproxy-executor.ts
@@ -316,7 +316,17 @@ export async function execClaudeWithCLIProxy(
   // 2. Handle special flags (use argsWithoutProxy - proxy flags already stripped)
   const forceAuth = argsWithoutProxy.includes('--auth');
   const pasteCallback = argsWithoutProxy.includes('--paste-callback');
+  const portForward = argsWithoutProxy.includes('--port-forward');
   const forceHeadless = argsWithoutProxy.includes('--headless');
+
+  // Validate conflicting flags
+  if (pasteCallback && portForward) {
+    console.error(fail('Cannot use --paste-callback with --port-forward'));
+    console.error('    --paste-callback: Manually paste OAuth redirect URL');
+    console.error('    --port-forward: Use SSH port forwarding for callback');
+    process.exit(1);
+  }
+
   const forceLogout = argsWithoutProxy.includes('--logout');
   const forceConfig = argsWithoutProxy.includes('--config');
   const addAccount = argsWithoutProxy.includes('--add');
@@ -548,6 +558,7 @@ export async function execClaudeWithCLIProxy(
         ...(setNickname ? { nickname: setNickname } : {}),
         ...(noIncognito ? { noIncognito: true } : {}),
         ...(pasteCallback ? { pasteCallback: true } : {}),
+        ...(portForward ? { portForward: true } : {}),
       });
       if (!authSuccess) {
         throw new Error(`Authentication required for ${providerConfig.displayName}`);
@@ -991,6 +1002,7 @@ export async function execClaudeWithCLIProxy(
   const ccsFlags = [
     '--auth',
     '--paste-callback',
+    '--port-forward',
     '--headless',
     '--logout',
     '--config',
diff --git a/src/commands/help-command.ts b/src/commands/help-command.ts
index 6152ce76..1dd631dd 100644
--- a/src/commands/help-command.ts
+++ b/src/commands/help-command.ts
@@ -184,6 +184,7 @@ Run ${color('ccs config', 'command')} for web dashboard`.trim();
       ],
       ['ccs <provider> --logout', 'Clear authentication'],
       ['ccs <provider> --headless', 'Headless auth (for SSH)'],
+      ['ccs <provider> --port-forward', 'Force port-forwarding mode (skip prompt)'],
       ['ccs kiro --import', 'Import token from Kiro IDE'],
       ['ccs kiro --incognito', 'Use incognito browser (default: normal)'],
       ['ccs codex "explain code"', 'Use with prompt'],