diff --git a/cli.py b/cli.py
index ce4f8eb43ec..032fbb4c475 100644
--- a/cli.py
+++ b/cli.py
@@ -2360,6 +2360,89 @@ def _strip_leaked_bracketed_paste_wrappers(text: str) -> str:
     return text
 
 
+def _apply_bracketed_paste_timeout_patch() -> None:
+    """Patch prompt_toolkit to recover from torn bracketed-paste sequences.
+
+    prompt_toolkit's ``Vt100Parser.feed()`` buffers all input while waiting
+    for the ESC[201~ end mark.  If a terminal drops that end mark (terminal
+    race, torn write, SSH glitch, macOS sleep/wake), input appears frozen
+    forever — the only recovery used to be killing the tab.
+
+    This patch wraps ``Vt100Parser.feed`` so that bracketed-paste mode
+    flushes buffered content as a normal ``BracketedPaste`` event after
+    ``_BP_TIMEOUT_S`` seconds without an end marker, then resumes normal
+    parsing.  See upstream issue #16263.
+
+    The patch is idempotent — repeated calls are no-ops via the
+    ``_hermes_bp_timeout_patched`` sentinel on the module.
+    """
+    try:
+        import prompt_toolkit.input.vt100_parser as _vt100_mod
+        from prompt_toolkit.keys import Keys as _PtKeys
+        from prompt_toolkit.key_binding.key_processor import KeyPress as _PtKeyPress
+
+        if getattr(_vt100_mod, "_hermes_bp_timeout_patched", False):
+            return
+
+        _BP_TIMEOUT_S = 2.0  # max time to wait for ESC[201~ before flushing
+
+        def _patched_vt100_feed(self_parser, data: str) -> None:
+            if self_parser._in_bracketed_paste:
+                self_parser._paste_buffer += data
+                end_mark = "\x1b[201~"
+
+                if end_mark in self_parser._paste_buffer:
+                    end_index = self_parser._paste_buffer.index(end_mark)
+                    paste_content = self_parser._paste_buffer[:end_index]
+                    self_parser.feed_key_callback(
+                        _PtKeyPress(_PtKeys.BracketedPaste, paste_content)
+                    )
+                    self_parser._in_bracketed_paste = False
+                    remaining = self_parser._paste_buffer[
+                        end_index + len(end_mark):
+                    ]
+                    self_parser._paste_buffer = ""
+                    self_parser._hermes_bp_start = None
+                    if remaining:
+                        _patched_vt100_feed(self_parser, remaining)
+                else:
+                    bp_start = getattr(self_parser, "_hermes_bp_start", None)
+                    now = time.monotonic()
+                    if bp_start is None:
+                        self_parser._hermes_bp_start = now
+                    elif now - bp_start > _BP_TIMEOUT_S:
+                        paste_content = self_parser._paste_buffer
+                        self_parser._in_bracketed_paste = False
+                        self_parser._paste_buffer = ""
+                        self_parser._hermes_bp_start = None
+                        if paste_content:
+                            self_parser.feed_key_callback(
+                                _PtKeyPress(_PtKeys.BracketedPaste, paste_content)
+                            )
+                            logger.warning(
+                                "Bracketed-paste timeout (%.1fs) — flushed %d bytes "
+                                "without end mark. Terminal may have dropped ESC[201~ "
+                                "(see #16263).",
+                                now - bp_start,
+                                len(paste_content),
+                            )
+            else:
+                # Normal mode — re-inline prompt_toolkit's normal feed path.
+                # Calling the original feed here would double-buffer after the
+                # bracketed-paste entry transition.
+                for i, c in enumerate(data):
+                    if self_parser._in_bracketed_paste:
+                        _patched_vt100_feed(self_parser, data[i:])
+                        break
+                    self_parser._input_parser.send(c)
+
+        _vt100_mod.Vt100Parser.feed = _patched_vt100_feed
+        _vt100_mod._hermes_bp_timeout_patched = True
+        logger.debug("Applied Vt100Parser bracketed-paste timeout patch (#16263)")
+    except Exception as exc:  # noqa: BLE001 — defensive: never break startup
+        logger.debug("Bracketed-paste timeout patch skipped: %s", exc)
+
+
 # Cursor Position Report (CPR / DSR) response, format ``ESC[<row>;<col>R``.
 # prompt_toolkit's _on_resize() + renderer send ``ESC[6n`` queries to the
 # terminal; under resize storms or tab switches the terminal's reply can
@@ -14151,6 +14234,10 @@ class HermesCLI:
         except Exception:
             pass
 
+        # Apply bracketed-paste timeout recovery so torn ESC[201~ end marks
+        # don't permanently freeze the input (issue #16263). Idempotent.
+        _apply_bracketed_paste_timeout_patch()
+
         _original_on_resize = app._on_resize
 
         def _resize_clear_ghosts():
diff --git a/tests/cli/test_bracketed_paste_timeout.py b/tests/cli/test_bracketed_paste_timeout.py
new file mode 100644
index 00000000000..3e99389339a
--- /dev/null
+++ b/tests/cli/test_bracketed_paste_timeout.py
@@ -0,0 +1,157 @@
+"""Tests for bracketed-paste timeout safety valve (#16263).
+
+Verifies the production helper in cli.py monkey-patches prompt_toolkit's
+Vt100Parser.feed() so the parser auto-escapes from bracketed-paste mode when
+the ESC[201~ end mark is never received.
+"""
+import ast
+import importlib
+import logging
+import time
+from pathlib import Path
+from unittest.mock import MagicMock
+
+from prompt_toolkit.keys import Keys
+
+
+ROOT = Path(__file__).resolve().parents[2]
+CLI_PATH = ROOT / "cli.py"
+
+
+def _load_production_patch_helper():
+    """Load cli._apply_bracketed_paste_timeout_patch without importing cli.
+
+    Importing cli.py pulls optional runtime deps that aren't required for this
+    parser-level regression.  AST-loading the exact helper keeps the test tied
+    to production code while avoiding unrelated import side effects.  If the
+    production helper is removed, this test fails.
+    """
+    source = CLI_PATH.read_text(encoding="utf-8")
+    tree = ast.parse(source)
+    helper_node = next(
+        (
+            node
+            for node in tree.body
+            if isinstance(node, ast.FunctionDef)
+            and node.name == "_apply_bracketed_paste_timeout_patch"
+        ),
+        None,
+    )
+    assert helper_node is not None, (
+        "cli.py must define _apply_bracketed_paste_timeout_patch()"
+    )
+    helper_source = ast.get_source_segment(source, helper_node)
+    namespace = {"time": time, "logger": logging.getLogger("test.cli")}
+    exec(helper_source, namespace)
+    return namespace["_apply_bracketed_paste_timeout_patch"]
+
+
+def _reset_and_apply_production_patch():
+    """Reload prompt_toolkit's parser and apply Hermes' production patch."""
+    import prompt_toolkit.input.vt100_parser as vt100_mod
+
+    vt100_mod = importlib.reload(vt100_mod)
+    # importlib.reload() preserves module dict entries that the reloaded source
+    # does not redefine, so clear Hermes' sentinel before re-applying.
+    if hasattr(vt100_mod, "_hermes_bp_timeout_patched"):
+        delattr(vt100_mod, "_hermes_bp_timeout_patched")
+    _load_production_patch_helper()()
+    assert getattr(vt100_mod, "_hermes_bp_timeout_patched", False)
+    return vt100_mod
+
+
+class TestBracketedPasteTimeout:
+    """Verify the Vt100Parser monkey-patch prevents frozen bracketed-paste."""
+
+    def _make_parser(self):
+        """Create a Vt100Parser after applying the production patch."""
+        vt100_mod = _reset_and_apply_production_patch()
+        callback = MagicMock()
+        parser = vt100_mod.Vt100Parser(callback)
+        return parser, callback
+
+    def test_normal_bracketed_paste_works(self):
+        """A complete bracketed-paste sequence should work normally."""
+        parser, callback = self._make_parser()
+        parser.feed("\x1b[200~hello world\x1b[201~")
+        callback.assert_called_once()
+        call_args = callback.call_args[0][0]
+        assert call_args.data == "hello world"
+
+    def test_incomplete_paste_times_out(self):
+        """If ESC[201~ is never received, parser should recover after timeout."""
+        parser, callback = self._make_parser()
+        parser.feed("\x1b[200~some pasted text")
+        assert parser._in_bracketed_paste
+
+        parser._hermes_bp_start = time.monotonic() - 3.0
+        parser.feed("more data")
+
+        assert not parser._in_bracketed_paste
+        assert callback.called
+
+    def test_timeout_preserves_buffered_content(self):
+        """Auto-escape should flush buffered content, not lose it."""
+        parser, callback = self._make_parser()
+        content = "line1\nline2\nline3"
+        parser.feed(f"\x1b[200~{content}")
+        parser._hermes_bp_start = time.monotonic() - 3.0
+        parser.feed("")
+
+        paste_events = [
+            c[0][0]
+            for c in callback.call_args_list
+            if hasattr(c[0][0], "key") and c[0][0].key == Keys.BracketedPaste
+        ]
+        assert len(paste_events) >= 1
+        assert content in paste_events[0].data
+
+    def test_normal_keys_after_timeout_recovery(self):
+        """After timeout recovery, normal key processing should resume."""
+        parser, callback = self._make_parser()
+        parser.feed("\x1b[200~stuck")
+        parser._hermes_bp_start = time.monotonic() - 3.0
+        parser.feed("")
+
+        assert not parser._in_bracketed_paste
+        callback.reset_mock()
+        parser.feed("a")
+        assert not parser._in_bracketed_paste
+
+    def test_no_timeout_when_end_mark_arrives_quickly(self):
+        """No timeout should fire if end mark arrives within the window."""
+        parser, callback = self._make_parser()
+        parser.feed("\x1b[200~quick paste\x1b[201~")
+        assert not parser._in_bracketed_paste
+        callback.assert_called_once()
+
+    def test_subsequent_data_after_incomplete_paste(self):
+        """Data arriving after a stuck paste should be processable."""
+        parser, callback = self._make_parser()
+        parser.feed("\x1b[200~content")
+        parser._hermes_bp_start = time.monotonic() - 5.0
+        parser.feed("x")
+
+        assert not parser._in_bracketed_paste
+        assert callback.call_count >= 1
+
+    def test_torn_end_mark_recovers(self):
+        """If end mark arrives split across feeds within timeout, it still works."""
+        parser, callback = self._make_parser()
+        parser.feed("\x1b[200~some content\x1b[20")
+        assert parser._in_bracketed_paste
+
+        parser.feed("1~")
+        assert not parser._in_bracketed_paste
+        callback.assert_called_once()
+        assert callback.call_args[0][0].data == "some content"
+
+    def test_no_timeout_under_threshold(self):
+        """Bracketed-paste mode should not timeout within the 2s window."""
+        parser, callback = self._make_parser()
+        parser.feed("\x1b[200~waiting")
+        parser._hermes_bp_start = time.monotonic() - 0.5
+        parser.feed("more waiting")
+
+        assert parser._in_bracketed_paste
+        assert not callback.called