diff --git a/packages/cli/src/ui/utils/commandUtils.test.ts b/packages/cli/src/ui/utils/commandUtils.test.ts
index 9a423e6abc..7686a0ab97 100644
--- a/packages/cli/src/ui/utils/commandUtils.test.ts
+++ b/packages/cli/src/ui/utils/commandUtils.test.ts
@@ -33,6 +33,7 @@ vi.mock('child_process');
 // fs (for /dev/tty)
 const mockFs = vi.hoisted(() => ({
   createWriteStream: vi.fn(),
+  writeSync: vi.fn(),
   constants: { W_OK: 2 },
 }));
 vi.mock('node:fs', () => ({
@@ -84,6 +85,7 @@ const resetEnv = () => {
   delete process.env['WSLENV'];
   delete process.env['WSL_INTEROP'];
   delete process.env['TERM'];
+  delete process.env['WT_SESSION'];
 };
 
 interface MockChildProcess extends EventEmitter {
@@ -477,6 +479,85 @@ describe('commandUtils', () => {
       expect(mockClipboardyWrite).toHaveBeenCalledWith('windows-native-test');
       expect(mockFs.createWriteStream).not.toHaveBeenCalled();
     });
+
+    it('uses OSC-52 on Windows Terminal (WT_SESSION) and prioritizes stdout', async () => {
+      mockProcess.platform = 'win32';
+      const stdoutStream = makeWritable({ isTTY: true });
+      const stderrStream = makeWritable({ isTTY: true });
+      Object.defineProperty(process, 'stdout', {
+        value: stdoutStream,
+        configurable: true,
+      });
+      Object.defineProperty(process, 'stderr', {
+        value: stderrStream,
+        configurable: true,
+      });
+
+      process.env['WT_SESSION'] = 'some-uuid';
+
+      const testText = 'windows-terminal-test';
+      await copyToClipboard(testText);
+
+      const b64 = Buffer.from(testText, 'utf8').toString('base64');
+      const expected = `${ESC}]52;c;${b64}${BEL}`;
+
+      expect(stdoutStream.write).toHaveBeenCalledWith(expected);
+      expect(stderrStream.write).not.toHaveBeenCalled();
+      expect(mockClipboardyWrite).not.toHaveBeenCalled();
+    });
+
+    it('uses fs.writeSync on Windows when stdout has an fd (bypassing Ink)', async () => {
+      mockProcess.platform = 'win32';
+      const stdoutStream = makeWritable({ isTTY: true });
+      // Simulate FD
+      (stdoutStream as unknown as { fd: number }).fd = 1;
+
+      Object.defineProperty(process, 'stdout', {
+        value: stdoutStream,
+        configurable: true,
+      });
+
+      process.env['WT_SESSION'] = 'some-uuid';
+
+      const testText = 'direct-write-test';
+      await copyToClipboard(testText);
+
+      const b64 = Buffer.from(testText, 'utf8').toString('base64');
+      const expected = `${ESC}]52;c;${b64}${BEL}`;
+
+      expect(mockFs.writeSync).toHaveBeenCalledWith(1, expected);
+      expect(stdoutStream.write).not.toHaveBeenCalled();
+      expect(mockClipboardyWrite).not.toHaveBeenCalled();
+    });
+
+    it('uses fs.writeSync on Windows when stderr has an fd and stdout is not a TTY', async () => {
+      mockProcess.platform = 'win32';
+      const stdoutStream = makeWritable({ isTTY: false });
+      const stderrStream = makeWritable({ isTTY: true });
+      // Simulate FD
+      (stderrStream as unknown as { fd: number }).fd = 2;
+
+      Object.defineProperty(process, 'stdout', {
+        value: stdoutStream,
+        configurable: true,
+      });
+      Object.defineProperty(process, 'stderr', {
+        value: stderrStream,
+        configurable: true,
+      });
+
+      process.env['WT_SESSION'] = 'some-uuid';
+
+      const testText = 'direct-write-stderr-test';
+      await copyToClipboard(testText);
+
+      const b64 = Buffer.from(testText, 'utf8').toString('base64');
+      const expected = `${ESC}]52;c;${b64}${BEL}`;
+
+      expect(mockFs.writeSync).toHaveBeenCalledWith(2, expected);
+      expect(stderrStream.write).not.toHaveBeenCalled();
+      expect(mockClipboardyWrite).not.toHaveBeenCalled();
+    });
   });
 
   describe('getUrlOpenCommand', () => {
diff --git a/packages/cli/src/ui/utils/commandUtils.ts b/packages/cli/src/ui/utils/commandUtils.ts
index d8894503e3..1f6d6f86bb 100644
--- a/packages/cli/src/ui/utils/commandUtils.ts
+++ b/packages/cli/src/ui/utils/commandUtils.ts
@@ -109,6 +109,18 @@ const pickTty = (): Promise<TtyTarget> =>
   });
 
 const getStdioTty = (): TtyTarget => {
+  // On Windows, prioritize stdout to prevent shell-specific formatting (e.g., PowerShell's
+  // red stderr) from corrupting the raw escape sequence payload.
+  if (process.platform === 'win32') {
+    if (process.stdout?.isTTY)
+      return { stream: process.stdout, closeAfter: false };
+    if (process.stderr?.isTTY)
+      return { stream: process.stderr, closeAfter: false };
+    return null;
+  }
+
+  // On non-Windows platforms, prioritize stderr to avoid polluting stdout,
+  // preserving it for potential redirection or piping.
   if (process.stderr?.isTTY)
     return { stream: process.stderr, closeAfter: false };
   if (process.stdout?.isTTY)
@@ -140,10 +152,13 @@ const isWSL = (): boolean =>
       process.env['WSL_INTEROP'],
   );
 
+const isWindowsTerminal = (): boolean =>
+  process.platform === 'win32' && Boolean(process.env['WT_SESSION']);
+
 const isDumbTerm = (): boolean => (process.env['TERM'] ?? '') === 'dumb';
 
 const shouldUseOsc52 = (tty: TtyTarget): boolean =>
-  Boolean(tty) && !isDumbTerm() && (isSSH() || isWSL());
+  Boolean(tty) && !isDumbTerm() && (isSSH() || isWSL() || isWindowsTerminal());
 
 const safeUtf8Truncate = (buf: Buffer, maxBytes: number): Buffer => {
   if (buf.length <= maxBytes) return buf;
@@ -176,6 +191,27 @@ const wrapForScreen = (seq: string): string => {
 
 const writeAll = (stream: Writable, data: string): Promise<void> =>
   new Promise<void>((resolve, reject) => {
+    // On Windows, writing directly to the underlying file descriptor bypasses
+    // application-level stream interception (e.g., by the Ink UI framework).
+    // This ensures the raw OSC-52 escape sequence reaches the terminal host uncorrupted.
+    const fd = (stream as unknown as { fd?: number }).fd;
+    if (
+      process.platform === 'win32' &&
+      typeof fd === 'number' &&
+      (stream === process.stdout || stream === process.stderr)
+    ) {
+      try {
+        fs.writeSync(fd, data);
+        resolve();
+        return;
+      } catch (e) {
+        debugLogger.warn(
+          'Direct write to TTY failed, falling back to stream write',
+          e,
+        );
+      }
+    }
+
     const onError = (err: unknown) => {
       cleanup();
       reject(err as Error);