1 files changed, 88 insertions, 0 deletions
diff --git a/tests/test_logging.py b/tests/test_logging.py
new file mode 100644
index 0000000..ef6fbd2
--- /dev/null
+++ b/tests/test_logging.py
@@ -0,0 +1,88 @@
+"""Tests for application file logging."""
+
+from __future__ import annotations
+
+import json
+import logging
+from pathlib import Path
+from unittest.mock import patch
+
+import pytest
+from starlette.testclient import TestClient
+
+from ollama_web.app import create_app
+from ollama_web.config import settings
+from ollama_web.tools.registry import default_registry
+
+
+def test_server_log_is_scoped_to_data_dir_and_app_lifespan(
+    tmp_path: Path,
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    data_dir = tmp_path / "data"
+    monkeypatch.setattr(settings, "data_dir", str(data_dir))
+    app_logger = logging.getLogger("ollama_web")
+    original_handlers = tuple(app_logger.handlers)
+    original_level = app_logger.level
+
+    app = create_app()
+    log_path = data_dir / "server.log"
+    assert not log_path.exists()
+
+    with TestClient(app):
+        assert len(app_logger.handlers) == len(original_handlers) + 1
+        logging.getLogger("ollama_web.test").info("lifespan log marker")
+
+    assert tuple(app_logger.handlers) == original_handlers
+    assert app_logger.level == original_level
+    assert log_path.read_text(encoding="utf-8").count("lifespan log marker") == 1
+
+    # Closing the lifespan must release the file on Windows as well.
+    log_path.unlink()
+    assert not log_path.exists()
+
+
+def test_repeated_app_lifespans_do_not_duplicate_log_handlers(
+    tmp_path: Path,
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    data_dir = tmp_path / "data"
+    monkeypatch.setattr(settings, "data_dir", str(data_dir))
+
+    with TestClient(create_app()):
+        logging.getLogger("ollama_web.test").info("first app marker")
+    with TestClient(create_app()):
+        logging.getLogger("ollama_web.test").info("second app marker")
+
+    content = (data_dir / "server.log").read_text(encoding="utf-8")
+    assert content.count("first app marker") == 1
+    assert content.count("second app marker") == 1
+
+
+def test_web_search_provider_error_is_written_to_server_log(
+    tmp_path: Path,
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    data_dir = tmp_path / "data"
+    monkeypatch.setattr(settings, "data_dir", str(data_dir))
+
+    class FailingDDGS:
+        def __enter__(self):
+            return self
+
+        def __exit__(self, *args):
+            return None
+
+        def text(self, query, max_results=5):
+            raise RuntimeError("403 Forbidden")
+
+    with patch("ollama_web.tools.search.DDGS", FailingDDGS), TestClient(create_app()):
+        result = json.loads(
+            default_registry().execute("web_search", {"query": "private search terms"})
+        )
+
+    assert result == {"error": "RuntimeError: 403 Forbidden"}
+    content = (data_dir / "server.log").read_text(encoding="utf-8")
+    assert "DuckDuckGo web search failed" in content
+    assert "RuntimeError: 403 Forbidden" in content
+    assert "private search terms" not in content