railmux 0.4.0.dev26__tar.gz → 0.4.0.dev28__tar.gz

{railmux-0.4.0.dev26 → railmux-0.4.0.dev28}/MANIFEST.in

@@ -1,3 +1,4 @@
 include tools/denested_transport_benchmark.py
 include tools/release_notes.py
 include tools/wheel_smoke.py
+include tools/windows_archive_smoke.py

{railmux-0.4.0.dev26/src/railmux.egg-info → railmux-0.4.0.dev28}/PKG-INFO

@@ -1,6 +1,6 @@
 Metadata-Version: 2.4
 Name: railmux
-Version: 0.4.0.dev26
+Version: 0.4.0.dev28
 Summary: Terminal UI to navigate, resume, and start Claude Code and Codex sessions
 Author-email: Rightglow <zhang.taian@foxmail.com>
 License-Expression: MIT

railmux-0.4.0.dev28/src/railmux/__init__.py

@@ -0,0 +1 @@
+__version__ = "0.4.0.dev28"

{railmux-0.4.0.dev26 → railmux-0.4.0.dev28}/src/railmux/windows_install_log.py

@@ -56,6 +56,10 @@ _PIP_NETWORK_ERROR_MARKERS = (
     "connection aborted",
     "temporary failure in name resolution",
 )
+_MSYS2_RESTART_MARKER = (
+    "to complete this update all msys2 processes including this terminal "
+    "will be closed"
+)
 _EXTRACTION_PERCENT_RE = re.compile(r"(?:^|\s)([0-9]{1,3})%\s")
 _PACKAGE_COUNT_RE = re.compile(r"^Packages \(([0-9]+)\)")
 _PACKAGE_DOWNLOAD_RE = re.compile(r"^\s*([^ ]+) downloading\.\.\.\s*$")
@@ -142,6 +146,7 @@ class InstallReporter:
         self._network_failure = False
         self._pip_network_failure = False
         self._hard_failed_hosts: set[str] = set()
+        self._msys2_restart_requested = False
 
     def __enter__(self) -> InstallReporter:
         self.path.parent.mkdir(parents=True, exist_ok=True)
@@ -209,6 +214,7 @@ class InstallReporter:
         self._network_failure = False
         self._pip_network_failure = False
         self._hard_failed_hosts.clear()
+        self._msys2_restart_requested = False
         self._write_log(f"\n--- {label} ---\n")
 
     def command_output(self, output: bytes | str | None) -> None:
@@ -259,6 +265,8 @@ class InstallReporter:
         if line.strip():
             self._tail.append(line)
         lowered = line.lower()
+        if _MSYS2_RESTART_MARKER in lowered:
+            self._msys2_restart_requested = True
         if any(marker in lowered for marker in _NETWORK_ERROR_MARKERS):
             self._network_failure = True
         if any(marker in lowered for marker in _PIP_NETWORK_ERROR_MARKERS):
@@ -364,6 +372,10 @@ class InstallReporter:
     def hard_failed_mirror_hosts(self) -> frozenset[str]:
         return frozenset(self._hard_failed_hosts)
 
+    @property
+    def command_requested_msys2_restart(self) -> bool:
+        return self._msys2_restart_requested
+
     def heartbeat(self) -> None:
         now = self._clock()
         if now - self._last_heartbeat < _HEARTBEAT_SECONDS:

{railmux-0.4.0.dev26 → railmux-0.4.0.dev28}/src/railmux/windows_msys2.py

@@ -80,6 +80,7 @@ MSYS2_BASE_LINEAGE_SHA256 = (
     "6fe0cc8154132040e034ff4daface2a4163a9d1f6ebaaa1133394bff460bd5cf"
 )
 MSYS2_RUNTIME_ID = f"msys2-{MSYS2_RELEASE}"
+_NATIVE_WINDOWS = os.name == "nt"
 RUNTIME_SCHEMA = 1
 
 _RUNTIME_OVERRIDE = "RAILMUX_MSYS2_ROOT"
@@ -118,6 +119,10 @@ _PACKAGE_URL_COMMAND = (
 _PACKAGE_INVENTORY_COMMAND = "set -o pipefail; pacman -Q | LC_ALL=C sort"
 _PACKAGE_INVENTORY_LIMIT = 1024 * 1024
 _CORE_RUNTIME_PACKAGES = ("tmux", "python", "python-pip")
+_MAX_BASE_UPDATE_PASSES = 3
+_PRIVATE_GPG_SHUTDOWN_COMMAND = (
+    "gpgconf --homedir /etc/pacman.d/gnupg --kill all"
+)
 _IN_USE_APPS_COMMAND = (
     "for f in /proc/[0-9]*/cmdline; do "
     "[ -r \"$f\" ] || continue; tr '\\0' '\\n' <\"$f\"; done"
@@ -621,6 +626,16 @@ def _ensure_safe_archive_directory(root: Path, parts: Sequence[str]) -> Path:
     return current
 
 
+def _apply_archive_mode(path: Path, mode: int) -> None:
+    if _NATIVE_WINDOWS:
+        # Windows chmod maps a missing owner-write bit to the NTFS read-only
+        # attribute; applying tar's POSIX 0444/0555 modes would prevent pacman
+        # from replacing those files during the first base update.
+        os.chmod(path, stat.S_IWRITE)
+    else:
+        os.chmod(path, mode)
+
+
 def _extract_msys2_archive(
     archive: Path,
     destination: Path,
@@ -696,7 +711,7 @@ def _extract_msys2_archive(
                                     )
                                 output.write(chunk)
                                 remaining -= len(chunk)
-                        os.chmod(target, member.mode & 0o777)
+                        _apply_archive_mode(target, member.mode & 0o777)
                     except RuntimeInstallError:
                         raise
                     except OSError as exc:
@@ -715,7 +730,7 @@ def _extract_msys2_archive(
                 "the verified MSYS2 archive expanded to an unexpected size"
             )
         for directory, mode in reversed(directories):
-            os.chmod(directory, mode)
+            _apply_archive_mode(directory, mode)
     except RuntimeInstallError:
         reporter.note(
             "MSYS2 archive extraction failed; the temporary base was not "
@@ -1613,12 +1628,23 @@ def _run_checked(
     if returncode:
         if allow_failure:
             return returncode
+        _explain_windows_status(returncode, reporter)
         reporter.command_failed(label, returncode)
         raise RuntimeInstallError(f"{label} failed with exit code {returncode}")
     reporter.command_succeeded()
     return 0
 
 
+def _explain_windows_status(returncode: int, reporter: InstallReporter) -> None:
+    if _NATIVE_WINDOWS and returncode & 0xFFFFFFFF == 0xC0000135:
+        reporter.note(
+            "Windows reported STATUS_DLL_NOT_FOUND outside a confirmed MSYS2 "
+            "core-update restart. Check whether security software quarantined "
+            "a file in the private MSYS2 staging tree.",
+            level="error",
+        )
+
+
 def _pacman_command(*, packages: bool, relaxed: bool) -> str:
     timeout = " --disable-download-timeout" if relaxed else ""
     needed = f" --needed {_PACMAN_PACKAGES}" if packages else ""
@@ -1627,10 +1653,11 @@ def _pacman_command(*, packages: bool, relaxed: bool) -> str:
         if not packages
         else ""
     )
+    operation = "-Syu" if packages else "-Syuu"
     return (
         'cache=$(cygpath -u "$1") && mkdir -p "$cache" && '
         f"{keyring}pacman --config {_PACMAN_CONFIG} --cachedir \"$cache\" "
-        f"-Syu --noconfirm{timeout}{needed}"
+        f"{operation} --noconfirm{timeout}{needed}"
     )
 
 
@@ -1676,7 +1703,8 @@ def _run_pacman_with_recovery(
     runner: Runner | None,
     label: str,
     mirror_optimizer: MirrorOptimizer,
-) -> None:
+    allow_core_restart: bool = False,
+) -> bool:
     argv = _bash_command(root, _pacman_command(packages=packages, relaxed=False), str(cache))
     returncode = _run_checked(
         argv,
@@ -1687,11 +1715,20 @@ def _run_pacman_with_recovery(
         progress="pacman",
         allow_failure=True,
     )
+    restart_requested = reporter.command_requested_msys2_restart
     if returncode == 0:
-        return
+        return restart_requested
+    if allow_core_restart and not packages and restart_requested:
+        reporter.note(
+            "MSYS2 replaced core runtime files and closed its own process as "
+            "expected; continuing from a fresh Windows-launched shell.",
+            level="warning",
+        )
+        return True
     network_failure = reporter.command_had_network_failure
     hard_failed_hosts = reporter.hard_failed_mirror_hosts
     if not network_failure:
+        _explain_windows_status(returncode, reporter)
         reporter.command_failed(label, returncode)
         raise RuntimeInstallError(f"{label} failed with exit code {returncode}")
     reporter.note(
@@ -1722,13 +1759,112 @@ def _run_pacman_with_recovery(
         _pacman_command(packages=packages, relaxed=True),
         str(cache),
     )
-    _run_checked(
+    retry_returncode = _run_checked(
         retry_argv,
         env=env,
         reporter=reporter,
         runner=runner,
         label=f"{label} resilient retry",
         progress="pacman",
+        allow_failure=True,
+    )
+    restart_requested = reporter.command_requested_msys2_restart
+    if retry_returncode == 0:
+        return restart_requested
+    if allow_core_restart and not packages and restart_requested:
+        reporter.note(
+            "MSYS2 replaced core runtime files and closed its own process as "
+            "expected; continuing from a fresh Windows-launched shell.",
+            level="warning",
+        )
+        return True
+    _explain_windows_status(retry_returncode, reporter)
+    reporter.command_failed(f"{label} resilient retry", retry_returncode)
+    raise RuntimeInstallError(
+        f"{label} resilient retry failed with exit code {retry_returncode}"
+    )
+
+
+def _run_base_update_with_restarts(
+    root: Path,
+    *,
+    cache: Path,
+    env: Mapping[str, str],
+    reporter: InstallReporter,
+    runner: Runner | None,
+    mirror_optimizer: MirrorOptimizer,
+) -> None:
+    """Run MSYS2's full upgrade in fresh processes until restart-safe."""
+    try:
+        for pass_number in range(1, _MAX_BASE_UPDATE_PASSES + 1):
+            restart_requested = _run_pacman_with_recovery(
+                root,
+                packages=False,
+                cache=cache,
+                env=env,
+                reporter=reporter,
+                runner=runner,
+                label=f"MSYS2 base update pass {pass_number}",
+                mirror_optimizer=mirror_optimizer,
+                allow_core_restart=pass_number < _MAX_BASE_UPDATE_PASSES,
+            )
+            if restart_requested:
+                reporter.note(
+                    "Starting a new MSYS2 process for the remaining update…"
+                )
+                continue
+            if pass_number == 1:
+                # MSYS2's supported unattended update procedure invokes Syuu
+                # twice, even when the first pass did not request a restart.
+                reporter.note(
+                    "Starting the required second MSYS2 update pass in a new "
+                    "process…"
+                )
+                continue
+            return
+        raise RuntimeInstallError(
+            "MSYS2 repeatedly requested a core-runtime restart; the temporary "
+            "base was not published"
+        )
+    finally:
+        _stop_private_gpg_agents(
+            root,
+            env=env,
+            reporter=reporter,
+            runner=runner,
+            strict=sys.exc_info()[0] is None,
+        )
+
+
+def _stop_private_gpg_agents(
+    root: Path,
+    *,
+    env: Mapping[str, str],
+    reporter: InstallReporter,
+    runner: Runner | None,
+    strict: bool,
+) -> None:
+    returncode = _run_checked(
+        _bash_command(root, _PRIVATE_GPG_SHUTDOWN_COMMAND),
+        env=env,
+        reporter=reporter,
+        runner=runner,
+        label="Stopping private MSYS2 keyring agents",
+        allow_failure=True,
+    )
+    if returncode == 0:
+        return
+    if not strict:
+        reporter.note(
+            "Could not stop a private MSYS2 keyring agent while recovering "
+            "from another installation failure.",
+            level="warning",
+        )
+        return
+    reporter.command_failed("Stopping private MSYS2 keyring agents", returncode)
+    raise RuntimeInstallError(
+        "stopping private MSYS2 keyring agents failed with exit code "
+        f"{returncode}"
     )
 
 
@@ -2382,16 +2518,20 @@ def install_managed_runtime(
                         "pacman is noninteractive; displayed [Y/n] prompts do "
                         "not require input."
                     )
+                    reporter.note(
+                        "Core updates may close the first MSYS2 process; "
+                        "Railmux will start the required fresh process "
+                        "automatically.",
+                        level="muted",
+                    )
                     package_cache = cache_base / f"pacman-{MSYS2_RUNTIME_ID}"
                     package_cache.mkdir(parents=True, exist_ok=True)
-                    _run_pacman_with_recovery(
+                    _run_base_update_with_restarts(
                         root,
-                        packages=False,
                         cache=package_cache,
                         env=child_env,
                         reporter=reporter,
                         runner=runner,
-                        label="MSYS2 base update",
                         mirror_optimizer=mirror_optimizer,
                     )
                     reporter.done()
@@ -2428,16 +2568,25 @@ def install_managed_runtime(
                         reporter=reporter,
                         runner=runner,
                     )
-                    _run_pacman_with_recovery(
-                        root,
-                        packages=True,
-                        cache=package_cache,
-                        env=child_env,
-                        reporter=reporter,
-                        runner=runner,
-                        label="MSYS2 package installation",
-                        mirror_optimizer=mirror_optimizer,
-                    )
+                    try:
+                        _run_pacman_with_recovery(
+                            root,
+                            packages=True,
+                            cache=package_cache,
+                            env=child_env,
+                            reporter=reporter,
+                            runner=runner,
+                            label="MSYS2 package installation",
+                            mirror_optimizer=mirror_optimizer,
+                        )
+                    finally:
+                        _stop_private_gpg_agents(
+                            root,
+                            env=child_env,
+                            reporter=reporter,
+                            runner=runner,
+                            strict=sys.exc_info()[0] is None,
+                        )
                     reporter.done()
 
                     identity = _ensure_base_content_identity(

{railmux-0.4.0.dev26 → railmux-0.4.0.dev28/src/railmux.egg-info}/PKG-INFO

@@ -1,6 +1,6 @@
 Metadata-Version: 2.4
 Name: railmux
-Version: 0.4.0.dev26
+Version: 0.4.0.dev28
 Summary: Terminal UI to navigate, resume, and start Claude Code and Codex sessions
 Author-email: Rightglow <zhang.taian@foxmail.com>
 License-Expression: MIT

{railmux-0.4.0.dev26 → railmux-0.4.0.dev28}/src/railmux.egg-info/SOURCES.txt

@@ -174,4 +174,5 @@ tests/test_windows_wrapper_contract.py
 tests/test_yolo_prompt.py
 tools/denested_transport_benchmark.py
 tools/release_notes.py
-tools/wheel_smoke.py
+tools/wheel_smoke.py
+tools/windows_archive_smoke.py

{railmux-0.4.0.dev26 → railmux-0.4.0.dev28}/tests/test_windows_install_log.py

@@ -2,8 +2,12 @@ from __future__ import annotations
 
 import io
 import os
+import subprocess
 import sys
 
+import pytest
+
+from railmux import windows_msys2
 from railmux.windows_install_log import InstallReporter, install_log_path
 from railmux.windows_msys2 import _run_checked
 
@@ -60,6 +64,22 @@ def test_verbose_reporter_streams_the_same_sanitized_output(tmp_path):
     assert "package 中文\nprogress\n" in path.read_text(encoding="utf-8")
 
 
+def test_reporter_recognizes_only_the_explicit_msys2_core_restart(tmp_path):
+    path = tmp_path / "install.log"
+    with InstallReporter(path, verbose=False, stream=io.StringIO()) as reporter:
+        reporter.command_started("first update")
+        reporter.command_output(
+            ":: To complete this update all MSYS2 processes including this "
+            "terminal will be closed. Confirm to proceed [Y/n]"
+        )
+        reporter.command_output_finished()
+        assert reporter.command_requested_msys2_restart
+
+        reporter.command_started("second update")
+        reporter.command_output("warning: terminate other MSYS2 programs\n")
+        assert not reporter.command_requested_msys2_restart
+
+
 def test_verbose_reporter_never_fails_on_a_legacy_windows_console_codec(tmp_path):
     stream = Cp1252Stream()
     path = tmp_path / "install-0.4.0.dev7-20260803T000000Z-5.log"
@@ -194,6 +214,27 @@ def test_default_command_runner_uses_no_stdin_and_captures_utf8(tmp_path):
     assert "captured 中文" in path.read_text(encoding="utf-8")
 
 
+def test_windows_missing_dll_status_is_explained(tmp_path, monkeypatch):
+    stream = io.StringIO()
+    path = tmp_path / "install.log"
+    monkeypatch.setattr(windows_msys2, "_NATIVE_WINDOWS", True)
+
+    with InstallReporter(path, verbose=False, stream=stream) as reporter:
+        with pytest.raises(windows_msys2.RuntimeInstallError, match="3221225781"):
+            _run_checked(
+                ["fixture.exe"],
+                env={},
+                reporter=reporter,
+                runner=lambda *_args, **_kwargs: subprocess.CompletedProcess(
+                    [], 0xC0000135
+                ),
+                label="MSYS2 base update",
+            )
+
+    assert "STATUS_DLL_NOT_FOUND" in stream.getvalue()
+    assert "security software" in path.read_text(encoding="utf-8")
+
+
 def test_compact_reporter_surfaces_extraction_and_package_progress(tmp_path):
     stream = io.StringIO()
     path = tmp_path / "install-0.4.0.dev8-20260803T000000Z-7.log"

{railmux-0.4.0.dev26 → railmux-0.4.0.dev28}/tests/test_windows_msys2.py

@@ -3,7 +3,9 @@ from __future__ import annotations
 import hashlib
 import io
 import json
+import os
 import re
+import stat
 import subprocess
 import tarfile
 from contextlib import contextmanager
@@ -795,6 +797,8 @@ def test_install_is_staged_and_activated_only_after_exact_probe(tmp_path):
         ).read_text(encoding="utf-8")
     )["railmux"] == VERSION
     joined = [" ".join(command) for command in commands]
+    base_updates = [command for command in joined if "-Syuu --noconfirm" in command]
+    assert len(base_updates) == 2
     assert any("-Syu --noconfirm" in command for command in joined)
     assert any("--needed tmux python python-pip" in command for command in joined)
     assert any('python -m venv "$1/venv"' in command for command in joined)
@@ -804,7 +808,8 @@ def test_install_is_staged_and_activated_only_after_exact_probe(tmp_path):
     assert len(logs) == 1
     log = logs[0].read_text(encoding="utf-8")
     assert "[1/7] Preparing verified MSYS2" in log
-    assert "--- MSYS2 base update ---" in log
+    assert "--- MSYS2 base update pass 1 ---" in log
+    assert "--- MSYS2 base update pass 2 ---" in log
     assert "Installation completed successfully" in log
     config = runtime.root / "etc" / "railmux-pacman.conf"
     assert "[msys]" in config.read_text(encoding="utf-8")
@@ -1291,12 +1296,16 @@ def test_tar_xz_extraction_is_internal_bounded_and_progress_visible(
         _tar_directory("msys64"),
         _tar_directory("msys64/usr"),
         _tar_file("msys64/usr/bash.exe", b"verified bash"),
+        _tar_file("msys64/usr/read-only-upstream", b"must stay writable"),
     ]
+    entries[-1][0].mode = 0o444
     archive = tmp_path / MSYS2_ARCHIVE_NAME
     _write_test_tar(archive, entries)
-    monkeypatch.setattr(windows_msys2, "MSYS2_ARCHIVE_MEMBER_COUNT", 3)
+    monkeypatch.setattr(windows_msys2, "MSYS2_ARCHIVE_MEMBER_COUNT", 4)
     monkeypatch.setattr(
-        windows_msys2, "MSYS2_ARCHIVE_UNPACKED_SIZE", len(b"verified bash")
+        windows_msys2,
+        "MSYS2_ARCHIVE_UNPACKED_SIZE",
+        len(b"verified bash") + len(b"must stay writable"),
     )
     destination = tmp_path / "stage"
     destination.mkdir()
@@ -1309,12 +1318,34 @@ def test_tar_xz_extraction_is_internal_bounded_and_progress_visible(
     assert (destination / "msys64" / "usr" / "bash.exe").read_bytes() == (
         b"verified bash"
     )
+    package_owned = destination / "msys64" / "usr" / "read-only-upstream"
+    if os.name == "nt":
+        readonly = getattr(stat, "FILE_ATTRIBUTE_READONLY", 0x1)
+        assert not getattr(package_owned.stat(), "st_file_attributes", 0) & readonly
+    else:
+        assert stat.S_IMODE(package_owned.stat().st_mode) == 0o444
     rendered = output.getvalue()
-    assert "Extracting private runtime: 1/3 files (33%)" in rendered
-    assert "Extracting private runtime: 3/3 files (100%)" in rendered
+    assert "Extracting private runtime: 1/4 files (25%)" in rendered
+    assert "Extracting private runtime: 4/4 files (100%)" in rendered
     assert "MSYS2 archive extraction" in log.read_text(encoding="utf-8")
 
 
+def test_native_windows_extraction_clears_posix_read_only_modes(
+    tmp_path, monkeypatch,
+):
+    path = tmp_path / "package-owned"
+    path.write_bytes(b"fixture")
+    applied = []
+    monkeypatch.setattr(windows_msys2, "_NATIVE_WINDOWS", True)
+    monkeypatch.setattr(
+        windows_msys2.os, "chmod", lambda target, mode: applied.append((target, mode))
+    )
+
+    windows_msys2._apply_archive_mode(path, 0o444)
+
+    assert applied == [(path, stat.S_IWRITE)]
+
+
 @pytest.mark.parametrize(
     ("member", "message"),
     [
@@ -1444,6 +1475,112 @@ def test_pacman_network_failure_retries_with_cache_and_relaxed_timeout(tmp_path)
     assert f"Server = {repo}" in rendered
 
 
+def test_base_update_restarts_after_confirmed_core_shutdown(tmp_path):
+    attempts = []
+    restart = (
+        b"upgrading msys2-runtime...\n"
+        b":: To complete this update all MSYS2 processes including this "
+        b"terminal will be closed. Confirm to proceed [Y/n]\n"
+    )
+
+    def runner(argv, *, env, check):
+        attempts.append(argv)
+        update_attempts = [item for item in attempts if "-Syuu" in item[4]]
+        if len(update_attempts) == 1 and "-Syuu" in argv[4]:
+            return completed(argv, returncode=0xC0000135, stdout=restart)
+        return completed(argv, stdout=b"there is nothing to do\n")
+
+    stream = io.StringIO()
+    with InstallReporter(
+        tmp_path / "install.log", verbose=False, stream=stream
+    ) as reporter:
+        windows_msys2._run_base_update_with_restarts(
+            tmp_path / "msys64",
+            cache=tmp_path / "cache",
+            env={},
+            reporter=reporter,
+            runner=runner,
+            mirror_optimizer=lambda _root: PacmanMirrorDecision(
+                None, None, False, (), ()
+            ),
+        )
+
+    updates = [argv for argv in attempts if "-Syuu --noconfirm" in argv[4]]
+    assert len(updates) == 2
+    assert updates[0][0] == updates[1][0]
+    assert windows_msys2._PRIVATE_GPG_SHUTDOWN_COMMAND in attempts[-1][4]
+    rendered = stream.getvalue()
+    assert "closed its own process as expected" in rendered
+    assert "failed with exit code" not in rendered
+
+
+def test_base_update_does_not_mask_unconfirmed_missing_dll(tmp_path, monkeypatch):
+    monkeypatch.setattr(windows_msys2, "_NATIVE_WINDOWS", True)
+    attempts = []
+
+    def runner(argv, *, env, check):
+        attempts.append(argv)
+        if windows_msys2._PRIVATE_GPG_SHUTDOWN_COMMAND in argv[4]:
+            return completed(argv)
+        return completed(
+            argv,
+            returncode=0xC0000135,
+            stdout=b"upgrading msys2-runtime...\n",
+        )
+
+    stream = io.StringIO()
+    with InstallReporter(
+        tmp_path / "install.log", verbose=False, stream=stream
+    ) as reporter:
+        with pytest.raises(RuntimeInstallError, match="3221225781"):
+            windows_msys2._run_base_update_with_restarts(
+                tmp_path / "msys64",
+                cache=tmp_path / "cache",
+                env={},
+                reporter=reporter,
+                runner=runner,
+                mirror_optimizer=lambda _root: PacmanMirrorDecision(
+                    None, None, False, (), ()
+                ),
+            )
+
+    updates = [argv for argv in attempts if "-Syuu --noconfirm" in argv[4]]
+    assert len(updates) == 1
+    assert "outside a confirmed MSYS2 core-update restart" in stream.getvalue()
+
+
+def test_base_update_restart_loop_is_bounded(tmp_path):
+    attempts = []
+    restart = (
+        b":: To complete this update all MSYS2 processes including this "
+        b"terminal will be closed. Confirm to proceed [Y/n]\n"
+    )
+
+    def runner(argv, *, env, check):
+        attempts.append(argv)
+        if windows_msys2._PRIVATE_GPG_SHUTDOWN_COMMAND in argv[4]:
+            return completed(argv)
+        return completed(argv, stdout=restart)
+
+    with InstallReporter(
+        tmp_path / "install.log", verbose=False, stream=io.StringIO()
+    ) as reporter:
+        with pytest.raises(RuntimeInstallError, match="repeatedly requested"):
+            windows_msys2._run_base_update_with_restarts(
+                tmp_path / "msys64",
+                cache=tmp_path / "cache",
+                env={},
+                reporter=reporter,
+                runner=runner,
+                mirror_optimizer=lambda _root: PacmanMirrorDecision(
+                    None, None, False, (), ()
+                ),
+            )
+
+    updates = [argv for argv in attempts if "-Syuu --noconfirm" in argv[4]]
+    assert len(updates) == windows_msys2._MAX_BASE_UPDATE_PASSES
+
+
 def test_completed_package_cache_count_ignores_signatures_partials_and_links(tmp_path):
     (tmp_path / "python.pkg.tar.zst").write_bytes(b"package")
     (tmp_path / "python.pkg.tar.zst.sig").write_bytes(b"signature")