test: add CLI tool hang regression tests

Add tests to verify CLI commands (tool, status) exit cleanly without hanging.

The tests reproduce a bug where CLI commands hang indefinitely after
displaying output. The root cause is that ensure_initialization() creates
database connections via asyncio.run() that are not cleaned up before the
event loop closes.

These tests will fail until the fix is applied.

🤖 Generated with [Claude Code](https://claude.com/claude-code)

Co-Authored-By: Claude Opus 4.5 <noreply@anthropic.com>
Signed-off-by: Cedric Hurst <cedric@spantree.net>

Author: divideby0

tests/cli/test_cli_tool_exit.py

@@ -0,0 +1,86 @@
+"""Test that CLI tool commands exit cleanly without hanging.
+
+This test ensures that CLI commands properly clean up database connections
+on exit, preventing process hangs. See GitHub issue for details.
+
+The issue occurs when:
+1. ensure_initialization() calls asyncio.run(initialize_app())
+2. initialize_app() creates global database connections via db.get_or_create_db()
+3. When asyncio.run() completes, the event loop closes
+4. But the global database engine holds async connections that prevent clean exit
+5. Process hangs indefinitely
+
+The fix ensures db.shutdown_db() is called before asyncio.run() returns.
+"""
+
+import subprocess
+import sys
+
+import pytest
+
+
+class TestCLIToolExit:
+    """Test that CLI tool commands exit cleanly."""
+
+    @pytest.mark.parametrize(
+        "command",
+        [
+            ["tool", "--help"],
+            ["tool", "write-note", "--help"],
+            ["tool", "read-note", "--help"],
+            ["tool", "search-notes", "--help"],
+            ["tool", "build-context", "--help"],
+            ["status"],  # Also affected by same issue
+        ],
+    )
+    def test_cli_command_exits_cleanly(self, command: list[str]):
+        """Test that CLI commands exit without hanging.
+
+        Each command should complete within the timeout without requiring
+        manual termination (Ctrl+C).
+        """
+        full_command = [sys.executable, "-m", "basic_memory.cli.main"] + command
+
+        try:
+            result = subprocess.run(
+                full_command,
+                capture_output=True,
+                text=True,
+                timeout=10.0,  # 10 second timeout - commands should complete in ~2s
+            )
+            # Command should exit with code 0 for --help
+            assert result.returncode == 0, f"Command failed: {result.stderr}"
+        except subprocess.TimeoutExpired:
+            pytest.fail(
+                f"Command '{' '.join(command)}' hung and did not exit within timeout. "
+                "This indicates database connections are not being cleaned up properly."
+            )
+
+    def test_ensure_initialization_exits_cleanly(self):
+        """Test that ensure_initialization doesn't cause process hang.
+
+        This test directly tests the initialization function that's called
+        by CLI commands, ensuring it cleans up database connections properly.
+        """
+        code = """
+import asyncio
+from basic_memory.config import ConfigManager
+from basic_memory.services.initialization import ensure_initialization
+
+app_config = ConfigManager().config
+ensure_initialization(app_config)
+print("OK")
+"""
+        try:
+            result = subprocess.run(
+                [sys.executable, "-c", code],
+                capture_output=True,
+                text=True,
+                timeout=10.0,
+            )
+            assert "OK" in result.stdout, f"Unexpected output: {result.stdout}"
+        except subprocess.TimeoutExpired:
+            pytest.fail(
+                "ensure_initialization() caused process hang. "
+                "Database connections are not being cleaned up before event loop closes."
+            )