From 7c96a0777da643746bd72c481b0dfa4c0be6dce5 Mon Sep 17 00:00:00 2001
From: Drew Cain <groksrc@gmail.com>
Date: Tue, 10 Mar 2026 23:13:54 -0500
Subject: [PATCH] fix(cli): handle brew outdated exit code 1 as outdated, not
 error

Signed-off-by: Drew Cain <groksrc@gmail.com>
---
 CHANGELOG.md                        |  7 +++++++
 src/basic_memory/cli/auto_update.py | 12 +++++-------
 tests/cli/test_auto_update.py       | 25 +++++++++++++++++++++++++
 3 files changed, 37 insertions(+), 7 deletions(-)

diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2be40fa6..6242aa67 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,13 @@
 
 ## Unreleased
 
+## v0.20.2 (2026-03-10)
+
+### Bug Fixes
+
+- Fix auto-update Homebrew detection: `brew outdated` exits 1 when a formula is outdated, not on error
+  - Previously treated exit code 1 as a failure, causing "Automatic update check failed" instead of detecting the available update
+
 ## v0.20.1 (2026-03-10)
 
 ### Bug Fixes
diff --git a/src/basic_memory/cli/auto_update.py b/src/basic_memory/cli/auto_update.py
index 586308e4..5a0fce3c 100644
--- a/src/basic_memory/cli/auto_update.py
+++ b/src/basic_memory/cli/auto_update.py
@@ -134,13 +134,11 @@ def _check_homebrew_update_available(silent: bool) -> tuple[bool, str | None]:
         silent=silent,
         capture_output=True,
     )
-    if result.returncode != 0:
-        stderr = (result.stderr or "").strip()
-        stdout = (result.stdout or "").strip()
-        detail = stderr or stdout or "brew outdated failed"
-        raise RuntimeError(detail)
-
-    is_outdated = bool((result.stdout or "").strip())
+    # Trigger: brew outdated exits 1 when the formula IS outdated (with name on stdout).
+    # Why: non-zero exit here means "outdated", not "error".
+    # Outcome: check stdout for the package name to determine outdated status.
+    stdout = (result.stdout or "").strip()
+    is_outdated = PACKAGE_NAME in stdout
     return is_outdated, None
 
 
diff --git a/tests/cli/test_auto_update.py b/tests/cli/test_auto_update.py
index 25009d78..0e404492 100644
--- a/tests/cli/test_auto_update.py
+++ b/tests/cli/test_auto_update.py
@@ -12,6 +12,7 @@ from basic_memory.cli.auto_update import (
     AutoUpdateResult,
     AutoUpdateStatus,
     InstallSource,
+    _check_homebrew_update_available,
     _is_interactive_session,
     detect_install_source,
     maybe_run_periodic_auto_update,
@@ -129,6 +130,30 @@ def test_force_bypasses_auto_update_disabled(monkeypatch, tmp_path):
     assert manager.save_calls == 1
 
 
+def test_check_homebrew_update_available_exit_code_1_means_outdated(monkeypatch):
+    """brew outdated exits 1 when the formula is outdated, not on error."""
+
+    def _fake_run(command, **kwargs):
+        return subprocess.CompletedProcess(
+            command, 1, stdout="basicmachines-co/basic-memory/basic-memory\n", stderr=""
+        )
+
+    monkeypatch.setattr("basic_memory.cli.auto_update._run_subprocess", _fake_run)
+    is_outdated, _ = _check_homebrew_update_available(silent=False)
+    assert is_outdated is True
+
+
+def test_check_homebrew_update_available_exit_code_0_means_up_to_date(monkeypatch):
+    """brew outdated exits 0 when the formula is up to date."""
+
+    def _fake_run(command, **kwargs):
+        return subprocess.CompletedProcess(command, 0, stdout="", stderr="")
+
+    monkeypatch.setattr("basic_memory.cli.auto_update._run_subprocess", _fake_run)
+    is_outdated, _ = _check_homebrew_update_available(silent=False)
+    assert is_outdated is False
+
+
 def test_homebrew_outdated_triggers_upgrade(monkeypatch, tmp_path):
     config = _base_config(tmp_path)
     manager = StubConfigManager(config)