fix(update): refresh brew tap before upgrade and verify result

CHANGELOG.md

@@ -15,6 +15,8 @@ GitHub Releases page; `0.8.0` is the new starting line.
 
 ## Unreleased
 
+- **Homebrew updater no longer no-ops or false-reports success.** `pythinker update` on a Homebrew install now runs `brew update` to refresh the tap before `brew upgrade`, so a stale local tap clone can't pin the old formula and silently no-op ("0.37.0 already installed"). After upgrading it re-checks the installed version via `brew list --versions` and reports a clear failure instead of "Updated successfully!" when the version did not actually advance.
+
 ## 0.38.0 (2026-06-08)
 
 - **Quieter `/login`.** Logging in no longer prints a `RuntimeWarning` about an un-awaited `redraw_in_future` coroutine. The prompt redraw throttle now uses a coroutine-free path (`max_render_postpone_time`), eliminating the warning emitted during the login prompt handoff.

src/pythinker_code/ui/shell/update.py

@@ -648,6 +648,36 @@ def _is_homebrew_upgrade_command(command: list[str]) -> bool:
     return len(command) >= 3 and command[:2] == ["brew", "upgrade"]
 
 
+def _installed_homebrew_version() -> str | None:
+    """Return the highest pythinker-code version Homebrew reports as installed.
+
+    Shelling out is required: the running interpreter's own
+    ``importlib.metadata`` still reports the pre-upgrade version until the
+    process restarts, so it cannot confirm an in-place upgrade. ``None`` means
+    "could not determine" (brew missing, formula not found, parse failure) — the
+    caller treats that as inconclusive rather than a failed upgrade.
+    """
+    try:
+        result = subprocess.run(
+            ["brew", "list", "--versions", "pythinker-code"],
+            capture_output=True,
+            text=True,
+            encoding="utf-8",
+            errors="replace",
+            env=get_clean_env(),
+            timeout=5,
+        )
+    except (OSError, subprocess.SubprocessError):
+        logger.exception("Failed to read installed Homebrew version:")
+        return None
+    if result.returncode != 0:
+        return None
+    versions = re.findall(r"\d+\.\d+\.\d+", result.stdout)
+    if not versions:
+        return None
+    return max(versions, key=semver_tuple)
+
+
 def _native_update_asset_name(version: str) -> str | None:
     linux_package_kind = _installed_linux_package_kind()
     if _is_windows():
@@ -1316,6 +1346,30 @@ def _print(message: str) -> None:
         _print(f"[{_t.muted}]The upgrade will continue in a new process.[/]")
         sys.exit(0)
 
+    if _is_homebrew_upgrade_command(upgrade_command):
+        # `brew upgrade <formula>` resolves against the locally-cloned tap
+        # formula; a stale clone pins the old version and the upgrade silently
+        # no-ops ("already installed"). Refresh the tap first. Best-effort: if
+        # the refresh fails we still attempt the upgrade, and the post-upgrade
+        # version check below catches a no-op.
+        _print(f"[{_t.muted}]Refreshing Homebrew metadata: brew update[/]")
+        try:
+            # --quiet keeps the refresh from dumping the host's full outdated
+            # formula/cask list (often dozens of unrelated lines) before our
+            # upgrade output.
+            refresh_code = _run_upgrade_command(
+                ["brew", "update", "--quiet"],
+                print_output=print_output,
+                output_callback=output_callback,
+            )
+        except OSError:
+            logger.exception("brew update failed to launch:")
+        else:
+            if refresh_code != 0:
+                logger.warning(
+                    "brew update exited {code}; continuing with upgrade", code=refresh_code
+                )
+
     try:
         returncode = _run_upgrade_command(
             upgrade_command,
@@ -1329,6 +1383,20 @@ def _print(message: str) -> None:
         return UpdateResult.FAILED
 
     if returncode == 0:
+        if _is_homebrew_upgrade_command(upgrade_command):
+            installed = _installed_homebrew_version()
+            if installed is not None and semver_tuple(installed) < semver_tuple(latest_version):
+                # brew exited 0 without changing anything (stale tap / no-op).
+                # Reporting success here is the bug we are fixing: don't.
+                _print(
+                    f"[{_t.error}]Homebrew exited cleanly but pythinker-code is "
+                    f"still {installed}, not {latest_version}.[/]"
+                )
+                _print(
+                    f"[{_t.warning}]The Homebrew tap metadata looks stale. "
+                    "Run 'brew update' and try '/update' again.[/]"
+                )
+                return UpdateResult.FAILED
         _print(f"[{_t.success}]Updated successfully![/]")
         _print(f"[{_t.warning}]Restart Pythinker CLI to use the new version.[/]")
         return UpdateResult.UPDATED

tests/ui_and_conv/test_shell_update.py

@@ -1262,3 +1262,116 @@ def test_update_prompt_text_renders_managed_channel_hint(monkeypatch):
     rendered = text.plain
     assert "docker" in rendered
     assert update.MANAGED_CHANNEL_MARKER not in rendered
+
+
+# ---------------------------------------------------------------------------
+# Homebrew upgrade: refresh tap before upgrade + verify version advanced
+#
+# Regression: `brew upgrade <formula>` reads the locally-cloned tap formula.
+# With a stale clone, the upgrade no-ops ("0.37.0 already installed") yet the
+# updater (which only checked the exit code) printed "Updated successfully!".
+# ---------------------------------------------------------------------------
+
+
+def _brew_upgrade_do_update_env(monkeypatch, tmp_path):
+    """Wire do_update onto the Homebrew upgrade path with no real network/brew."""
+
+    async def fake_get_latest(session):
+        return "999.0.0"
+
+    async def fake_unavailable(session, latest_version: str, upgrade_command: list[str]):
+        return None
+
+    monkeypatch.setattr(update, "LATEST_VERSION_FILE", tmp_path / "latest.txt")
+    monkeypatch.setattr(update, "_get_latest_version", fake_get_latest)
+    monkeypatch.setattr(update, "_update_candidate_unavailable_reason", fake_unavailable)
+    monkeypatch.setattr(
+        update, "_detect_upgrade_command", lambda: ["brew", "upgrade", "pythinker-code"]
+    )
+
+
+@pytest.mark.asyncio
+async def test_do_update_brew_refreshes_tap_before_upgrade(monkeypatch, tmp_path):
+    """`brew update` must run before `brew upgrade` so a stale tap clone can't
+    pin the old formula version and silently no-op the upgrade."""
+    ran: list[list[str]] = []
+
+    def fake_run_upgrade_command(command, *, print_output: bool, output_callback):
+        ran.append(command)
+        return 0
+
+    _brew_upgrade_do_update_env(monkeypatch, tmp_path)
+    monkeypatch.setattr(update, "_run_upgrade_command", fake_run_upgrade_command)
+    # Version genuinely advanced after the upgrade.
+    monkeypatch.setattr(update, "_installed_homebrew_version", lambda: "999.0.0")
+
+    result = await update.do_update(print_output=False)
+
+    assert result is update.UpdateResult.UPDATED
+    assert ran == [["brew", "update", "--quiet"], ["brew", "upgrade", "pythinker-code"]]
+
+
+@pytest.mark.asyncio
+async def test_do_update_brew_reports_failure_when_version_unchanged(monkeypatch, tmp_path):
+    """A no-op `brew upgrade` exits 0; the updater must NOT claim success when
+    the installed version did not advance to the target."""
+    messages: list[str] = []
+
+    def fake_run_upgrade_command(command, *, print_output: bool, output_callback):
+        return 0
+
+    _brew_upgrade_do_update_env(monkeypatch, tmp_path)
+    monkeypatch.setattr(update, "_run_upgrade_command", fake_run_upgrade_command)
+    # brew exited 0 but the keg is still the old version (stale tap).
+    monkeypatch.setattr(update, "_installed_homebrew_version", lambda: "0.37.0")
+
+    result = await update.do_update(print_output=False, output_callback=messages.append)
+
+    assert result is update.UpdateResult.FAILED
+    assert not any("Updated successfully" in m for m in messages)
+    assert any("still 0.37.0" in m for m in messages)
+    assert any("brew update" in m for m in messages)
+
+
+@pytest.mark.asyncio
+async def test_do_update_brew_continues_when_refresh_fails(monkeypatch, tmp_path):
+    """A failing `brew update` (e.g. transient network) must not block the
+    upgrade attempt — the upgrade still runs and can still succeed."""
+    ran: list[list[str]] = []
+
+    def fake_run_upgrade_command(command, *, print_output: bool, output_callback):
+        ran.append(command)
+        return 1 if command == ["brew", "update", "--quiet"] else 0
+
+    _brew_upgrade_do_update_env(monkeypatch, tmp_path)
+    monkeypatch.setattr(update, "_run_upgrade_command", fake_run_upgrade_command)
+    monkeypatch.setattr(update, "_installed_homebrew_version", lambda: "999.0.0")
+
+    result = await update.do_update(print_output=False)
+
+    assert result is update.UpdateResult.UPDATED
+    assert ran == [["brew", "update", "--quiet"], ["brew", "upgrade", "pythinker-code"]]
+
+
+def test_installed_homebrew_version_returns_max_installed(monkeypatch):
+    """Parses `brew list --versions`, returning the highest installed version."""
+
+    class FakeCompleted:
+        returncode = 0
+        stdout = "pythinker-code 0.37.0 0.38.0\n"
+
+    monkeypatch.setattr(update.subprocess, "run", lambda *a, **k: FakeCompleted())
+
+    assert update._installed_homebrew_version() == "0.38.0"
+
+
+def test_installed_homebrew_version_returns_none_on_failure(monkeypatch):
+    """A non-zero `brew list` (formula not found) yields None, not a crash."""
+
+    class FakeCompleted:
+        returncode = 1
+        stdout = ""
+
+    monkeypatch.setattr(update.subprocess, "run", lambda *a, **k: FakeCompleted())
+
+    assert update._installed_homebrew_version() is None