diff --git a/packages/cli/src/ui/utils/commandUtils.test.ts b/packages/cli/src/ui/utils/commandUtils.test.ts
index 722bcef18d..6133b33a38 100644
--- a/packages/cli/src/ui/utils/commandUtils.test.ts
+++ b/packages/cli/src/ui/utils/commandUtils.test.ts
@@ -15,6 +15,11 @@ import {
   getUrlOpenCommand,
 } from './commandUtils.js';
 
+// Constants used by OSC-52 tests
+const ESC = '\u001B';
+const BEL = '\u0007';
+const ST = '\u001B\\';
+
 // Mock clipboardy
 vi.mock('clipboardy', () => ({
   default: {
@@ -25,6 +30,14 @@ vi.mock('clipboardy', () => ({
 // Mock child_process
 vi.mock('child_process');
 
+// fs (for /dev/tty)
+const mockFs = vi.hoisted(() => ({
+  createWriteStream: vi.fn(),
+}));
+vi.mock('node:fs', () => ({
+  default: mockFs,
+}));
+
 // Mock process.platform for platform-specific tests
 const mockProcess = vi.hoisted(() => ({
   platform: 'darwin',
@@ -40,6 +53,36 @@ vi.stubGlobal(
   }),
 );
 
+const makeWritable = (opts?: { isTTY?: boolean; writeReturn?: boolean }) => {
+  const { isTTY = false, writeReturn = true } = opts ?? {};
+  const stream = Object.assign(new EventEmitter(), {
+    write: vi.fn().mockReturnValue(writeReturn),
+    end: vi.fn(),
+    destroy: vi.fn(),
+    isTTY,
+    once: EventEmitter.prototype.once,
+    on: EventEmitter.prototype.on,
+    off: EventEmitter.prototype.off,
+  }) as unknown as EventEmitter & {
+    write: Mock;
+    end: Mock;
+    isTTY?: boolean;
+  };
+  return stream;
+};
+
+const resetEnv = () => {
+  delete process.env['TMUX'];
+  delete process.env['STY'];
+  delete process.env['SSH_TTY'];
+  delete process.env['SSH_CONNECTION'];
+  delete process.env['SSH_CLIENT'];
+  delete process.env['WSL_DISTRO_NAME'];
+  delete process.env['WSLENV'];
+  delete process.env['WSL_INTEROP'];
+  delete process.env['TERM'];
+};
+
 interface MockChildProcess extends EventEmitter {
   stdin: EventEmitter & {
     write: Mock;
@@ -78,6 +121,23 @@ describe('commandUtils', () => {
 
     // Setup clipboardy mock
     mockClipboardyWrite = clipboardy.write as Mock;
+
+    // default: no /dev/tty available
+    mockFs.createWriteStream.mockImplementation(() => {
+      throw new Error('ENOENT');
+    });
+
+    // default: stdio are not TTY for tests unless explicitly set
+    Object.defineProperty(process, 'stderr', {
+      value: makeWritable({ isTTY: false }),
+      configurable: true,
+    });
+    Object.defineProperty(process, 'stdout', {
+      value: makeWritable({ isTTY: false }),
+      configurable: true,
+    });
+
+    resetEnv();
   });
 
   describe('isAtCommand', () => {
@@ -139,23 +199,160 @@ describe('commandUtils', () => {
   });
 
   describe('copyToClipboard', () => {
-    it('should successfully copy text to clipboard using clipboardy', async () => {
+    it('uses clipboardy when not in SSH/tmux/screen/WSL (even if TTYs exist)', async () => {
       const testText = 'Hello, world!';
       mockClipboardyWrite.mockResolvedValue(undefined);
 
+      // even if stderr/stdout are TTY, without the env signals we fallback
+      Object.defineProperty(process, 'stderr', {
+        value: makeWritable({ isTTY: true }),
+        configurable: true,
+      });
+      Object.defineProperty(process, 'stdout', {
+        value: makeWritable({ isTTY: true }),
+        configurable: true,
+      });
+
       await copyToClipboard(testText);
 
       expect(mockClipboardyWrite).toHaveBeenCalledWith(testText);
     });
 
-    it('should propagate errors from clipboardy', async () => {
-      const testText = 'Hello, world!';
-      const error = new Error('Clipboard error');
-      mockClipboardyWrite.mockRejectedValue(error);
+    it('writes OSC-52 to /dev/tty when in SSH', async () => {
+      const testText = 'abc';
+      const tty = makeWritable({ isTTY: true });
+      mockFs.createWriteStream.mockReturnValue(tty);
 
-      await expect(copyToClipboard(testText)).rejects.toThrow(
-        'Clipboard error',
-      );
+      process.env['SSH_CONNECTION'] = '1';
+
+      await copyToClipboard(testText);
+
+      const b64 = Buffer.from(testText, 'utf8').toString('base64');
+      const expected = `${ESC}]52;c;${b64}${BEL}`;
+
+      expect(tty.write).toHaveBeenCalledTimes(1);
+      expect((tty.write as Mock).mock.calls[0][0]).toBe(expected);
+      expect(tty.end).toHaveBeenCalledTimes(1); // /dev/tty closed after write
+      expect(mockClipboardyWrite).not.toHaveBeenCalled();
+    });
+
+    it('wraps OSC-52 for tmux', async () => {
+      const testText = 'tmux-copy';
+      const tty = makeWritable({ isTTY: true });
+      mockFs.createWriteStream.mockReturnValue(tty);
+
+      process.env['TMUX'] = '1';
+
+      await copyToClipboard(testText);
+
+      const written = (tty.write as Mock).mock.calls[0][0] as string;
+      // Starts with tmux DCS wrapper and ends with ST
+      expect(written.startsWith(`${ESC}Ptmux;`)).toBe(true);
+      expect(written.endsWith(ST)).toBe(true);
+      // ESC bytes in payload are doubled
+      expect(written).toContain(`${ESC}${ESC}]52;c;`);
+      expect(mockClipboardyWrite).not.toHaveBeenCalled();
+    });
+
+    it('wraps OSC-52 for GNU screen with chunked DCS', async () => {
+      // ensure payload > chunk size (240) so there are multiple chunks
+      const testText = 'x'.repeat(1200);
+      const tty = makeWritable({ isTTY: true });
+      mockFs.createWriteStream.mockReturnValue(tty);
+
+      process.env['STY'] = 'screen-session';
+
+      await copyToClipboard(testText);
+
+      const written = (tty.write as Mock).mock.calls[0][0] as string;
+      const chunkStarts = (written.match(new RegExp(`${ESC}P`, 'g')) || [])
+        .length;
+      const chunkEnds = written.split(ST).length - 1;
+
+      expect(chunkStarts).toBeGreaterThan(1);
+      expect(chunkStarts).toBe(chunkEnds);
+      expect(written).toContain(']52;c;'); // contains base OSC-52 marker
+      expect(mockClipboardyWrite).not.toHaveBeenCalled();
+    });
+
+    it('falls back to stderr when /dev/tty unavailable and stderr is a TTY', async () => {
+      const testText = 'stderr-tty';
+      const stderrStream = makeWritable({ isTTY: true });
+      Object.defineProperty(process, 'stderr', {
+        value: stderrStream,
+        configurable: true,
+      });
+
+      process.env['SSH_TTY'] = '/dev/pts/1';
+
+      await copyToClipboard(testText);
+
+      const b64 = Buffer.from(testText, 'utf8').toString('base64');
+      const expected = `${ESC}]52;c;${b64}${BEL}`;
+
+      expect(stderrStream.write).toHaveBeenCalledWith(expected);
+      expect(mockClipboardyWrite).not.toHaveBeenCalled();
+    });
+
+    it('falls back to clipboardy when no TTY is available', async () => {
+      const testText = 'no-tty';
+      mockClipboardyWrite.mockResolvedValue(undefined);
+
+      // /dev/tty throws; stderr/stdout are non-TTY by default
+      process.env['SSH_CLIENT'] = 'client';
+
+      await copyToClipboard(testText);
+
+      expect(mockClipboardyWrite).toHaveBeenCalledWith(testText);
+    });
+
+    it('resolves on drain when backpressure occurs', async () => {
+      const tty = makeWritable({ isTTY: true, writeReturn: false });
+      mockFs.createWriteStream.mockReturnValue(tty);
+      process.env['SSH_CONNECTION'] = '1';
+
+      const p = copyToClipboard('drain-test');
+      setTimeout(() => {
+        tty.emit('drain');
+      }, 0);
+      await expect(p).resolves.toBeUndefined();
+    });
+
+    it('propagates errors from OSC-52 write path', async () => {
+      const tty = makeWritable({ isTTY: true, writeReturn: false });
+      mockFs.createWriteStream.mockReturnValue(tty);
+      process.env['SSH_CONNECTION'] = '1';
+
+      const p = copyToClipboard('err-test');
+      setTimeout(() => {
+        tty.emit('error', new Error('tty error'));
+      }, 0);
+
+      await expect(p).rejects.toThrow('tty error');
+      expect(mockClipboardyWrite).not.toHaveBeenCalled();
+    });
+
+    it('does nothing for empty string', async () => {
+      await copyToClipboard('');
+      expect(mockClipboardyWrite).not.toHaveBeenCalled();
+      // ensure no accidental writes to stdio either
+      const stderrStream = process.stderr as unknown as { write: Mock };
+      const stdoutStream = process.stdout as unknown as { write: Mock };
+      expect(stderrStream.write).not.toHaveBeenCalled();
+      expect(stdoutStream.write).not.toHaveBeenCalled();
+    });
+
+    it('uses clipboardy when not in eligible env even if /dev/tty exists', async () => {
+      const tty = makeWritable({ isTTY: true });
+      mockFs.createWriteStream.mockReturnValue(tty);
+      const text = 'local-terminal';
+      mockClipboardyWrite.mockResolvedValue(undefined);
+
+      await copyToClipboard(text);
+
+      expect(mockClipboardyWrite).toHaveBeenCalledWith(text);
+      expect(tty.write).not.toHaveBeenCalled();
+      expect(tty.end).not.toHaveBeenCalled();
     });
   });
 
diff --git a/packages/cli/src/ui/utils/commandUtils.ts b/packages/cli/src/ui/utils/commandUtils.ts
index 68cabe2431..41519e0725 100644
--- a/packages/cli/src/ui/utils/commandUtils.ts
+++ b/packages/cli/src/ui/utils/commandUtils.ts
@@ -7,6 +7,8 @@
 import { debugLogger } from '@google/gemini-cli-core';
 import clipboardy from 'clipboardy';
 import type { SlashCommand } from '../commands/types.js';
+import fs from 'node:fs';
+import type { Writable } from 'node:stream';
 
 /**
  * Checks if a query string potentially represents an '@' command.
@@ -45,8 +47,146 @@ export const isSlashCommand = (query: string): boolean => {
   return true;
 };
 
-// Copies a string snippet to the clipboard
+const ESC = '\u001B';
+const BEL = '\u0007';
+const ST = '\u001B\\';
+
+const MAX_OSC52_SEQUENCE_BYTES = 100_000;
+const OSC52_HEADER = `${ESC}]52;c;`;
+const OSC52_FOOTER = BEL;
+const MAX_OSC52_BODY_B64_BYTES =
+  MAX_OSC52_SEQUENCE_BYTES -
+  Buffer.byteLength(OSC52_HEADER) -
+  Buffer.byteLength(OSC52_FOOTER);
+const MAX_OSC52_DATA_BYTES = Math.floor(MAX_OSC52_BODY_B64_BYTES / 4) * 3;
+
+// Conservative chunk size for GNU screen DCS passthrough.
+const SCREEN_DCS_CHUNK_SIZE = 240;
+
+type TtyTarget = { stream: Writable; closeAfter: boolean } | null;
+
+const pickTty = (): TtyTarget => {
+  // Prefer the controlling TTY to avoid interleaving escape sequences with piped stdout.
+  try {
+    const devTty = fs.createWriteStream('/dev/tty');
+    return { stream: devTty, closeAfter: true };
+  } catch {
+    // fall through
+  }
+  if (process.stderr?.isTTY)
+    return { stream: process.stderr, closeAfter: false };
+  if (process.stdout?.isTTY)
+    return { stream: process.stdout, closeAfter: false };
+  return null;
+};
+
+const inTmux = (): boolean =>
+  Boolean(
+    process.env['TMUX'] || (process.env['TERM'] ?? '').startsWith('tmux'),
+  );
+
+const inScreen = (): boolean =>
+  Boolean(
+    process.env['STY'] || (process.env['TERM'] ?? '').startsWith('screen'),
+  );
+
+const isSSH = (): boolean =>
+  Boolean(
+    process.env['SSH_TTY'] ||
+      process.env['SSH_CONNECTION'] ||
+      process.env['SSH_CLIENT'],
+  );
+
+const isWSL = (): boolean =>
+  Boolean(
+    process.env['WSL_DISTRO_NAME'] ||
+      process.env['WSLENV'] ||
+      process.env['WSL_INTEROP'],
+  );
+
+const isDumbTerm = (): boolean => (process.env['TERM'] ?? '') === 'dumb';
+
+const shouldUseOsc52 = (tty: TtyTarget): boolean =>
+  Boolean(tty) &&
+  !isDumbTerm() &&
+  (isSSH() || inTmux() || inScreen() || isWSL());
+
+const safeUtf8Truncate = (buf: Buffer, maxBytes: number): Buffer => {
+  if (buf.length <= maxBytes) return buf;
+  let end = maxBytes;
+  // Back up to the start of a UTF-8 code point if we cut through a continuation byte (10xxxxxx).
+  while (end > 0 && (buf[end - 1] & 0b1100_0000) === 0b1000_0000) end--;
+  return buf.subarray(0, end);
+};
+
+const buildOsc52 = (text: string): string => {
+  const raw = Buffer.from(text, 'utf8');
+  const safe = safeUtf8Truncate(raw, MAX_OSC52_DATA_BYTES);
+  const b64 = safe.toString('base64');
+  return `${OSC52_HEADER}${b64}${OSC52_FOOTER}`;
+};
+
+const wrapForTmux = (seq: string): string => {
+  // Double ESC bytes in payload without a control-character regex.
+  const doubledEsc = seq.split(ESC).join(ESC + ESC);
+  return `${ESC}Ptmux;${doubledEsc}${ST}`;
+};
+
+const wrapForScreen = (seq: string): string => {
+  let out = '';
+  for (let i = 0; i < seq.length; i += SCREEN_DCS_CHUNK_SIZE) {
+    out += `${ESC}P${seq.slice(i, i + SCREEN_DCS_CHUNK_SIZE)}${ST}`;
+  }
+  return out;
+};
+
+const writeAll = (stream: Writable, data: string): Promise<void> =>
+  new Promise<void>((resolve, reject) => {
+    const onError = (err: unknown) => {
+      cleanup();
+      reject(err as Error);
+    };
+    const onDrain = () => {
+      cleanup();
+      resolve();
+    };
+    const cleanup = () => {
+      stream.off('error', onError);
+      stream.off('drain', onDrain);
+      // Writable.write() handlers may not emit 'drain' if the first write succeeded.
+    };
+    stream.once('error', onError);
+    if (stream.write(data)) {
+      cleanup();
+      resolve();
+    } else {
+      stream.once('drain', onDrain);
+    }
+  });
+
+// Copies a string snippet to the clipboard with robust OSC-52 support.
 export const copyToClipboard = async (text: string): Promise<void> => {
+  if (!text) return;
+
+  const tty = pickTty();
+
+  if (shouldUseOsc52(tty)) {
+    const osc = buildOsc52(text);
+    const payload = inTmux()
+      ? wrapForTmux(osc)
+      : inScreen()
+        ? wrapForScreen(osc)
+        : osc;
+
+    await writeAll(tty!.stream, payload);
+
+    if (tty!.closeAfter) {
+      (tty!.stream as fs.WriteStream).end();
+    }
+    return;
+  }
+
+  // Local / non-TTY fallback
   await clipboardy.write(text);
 };