feat(logging): Implement session-based log organization

gui_2.py

@@ -263,7 +263,8 @@ class App:
         self._autosave_interval = 60.0
         self._last_autosave = time.time()
 
-        session_logger.open_session()
+        label = self.project.get("project", {}).get("name", "")
+        session_logger.open_session(label=label)
         self._init_ai_and_hooks()
 
     @property

gui_legacy.py

@@ -513,7 +513,8 @@ class App:
             "cache_creation_input_tokens": 0
         }
 
-        session_logger.open_session()
+        label = self.project.get("project", {}).get("name", "")
+        session_logger.open_session(label=label)
         ai_client.set_provider(self.current_provider, self.current_model)
         ai_client.confirm_and_run_callback = self._confirm_and_run
         ai_client.comms_log_callback = self._on_comms_entry

session_logger.py

@@ -26,46 +26,62 @@ _LOG_DIR = Path("./logs")
 _SCRIPTS_DIR = Path("./scripts/generated")
 
 _ts: str = ""            # session timestamp string  e.g. "20260301_142233"
+_session_id: str = ""    # YYYYMMDD_HHMMSS[_Label]
+_session_dir: Path = None # Path to the sub-directory for this session
 _seq: int = 0            # monotonic counter for script files this session
 _seq_lock = threading.Lock()
 
-_comms_fh = None         # file handle: logs/comms_<ts>.log
-_tool_fh  = None         # file handle: logs/toolcalls_<ts>.log
-_api_fh   = None         # file handle: logs/apihooks_<ts>.log - API hook calls
-_cli_fh   = None         # file handle: logs/clicalls_<ts>.log - CLI subprocess calls
+_comms_fh = None         # file handle: logs/<session_id>/comms.log
+_tool_fh  = None         # file handle: logs/<session_id>/toolcalls.log
+_api_fh   = None         # file handle: logs/<session_id>/apihooks.log
+_cli_fh   = None         # file handle: logs/<session_id>/clicalls.log
 
 
 def _now_ts() -> str:
     return datetime.datetime.now().strftime("%Y%m%d_%H%M%S")
 
 
-def open_session():
+def open_session(label: str | None = None):
     """
     Called once at GUI startup.  Creates the log directories if needed and
-    opens the two log files for this session.  Idempotent - a second call is
-    ignored.
+    opens the log files for this session within a sub-directory.
     """
-    global _ts, _comms_fh, _tool_fh, _api_fh, _cli_fh, _seq
+    global _ts, _session_id, _session_dir, _comms_fh, _tool_fh, _api_fh, _cli_fh, _seq
 
     if _comms_fh is not None:
         return  # already open
 
-    _LOG_DIR.mkdir(parents=True, exist_ok=True)
+    _ts = _now_ts()
+    _session_id = _ts
+    if label:
+        # Sanitize label: remove non-alphanumeric chars
+        safe_label = "".join(c if c.isalnum() or c in ("-", "_") else "_" for c in label)
+        _session_id += f"_{safe_label}"
+
+    _session_dir = _LOG_DIR / _session_id
+    _session_dir.mkdir(parents=True, exist_ok=True)
     _SCRIPTS_DIR.mkdir(parents=True, exist_ok=True)
 
-    _ts  = _now_ts()
     _seq = 0
 
-    _comms_fh = open(_LOG_DIR / f"comms_{_ts}.log", "w", encoding="utf-8", buffering=1)
-    _tool_fh  = open(_LOG_DIR / f"toolcalls_{_ts}.log", "w", encoding="utf-8", buffering=1)
-    _api_fh   = open(_LOG_DIR / f"apihooks_{_ts}.log", "w", encoding="utf-8", buffering=1)
-    _cli_fh   = open(_LOG_DIR / f"clicalls_{_ts}.log", "w", encoding="utf-8", buffering=1) # New log file handle
+    _comms_fh = open(_session_dir / "comms.log", "w", encoding="utf-8", buffering=1)
+    _tool_fh  = open(_session_dir / "toolcalls.log", "w", encoding="utf-8", buffering=1)
+    _api_fh   = open(_session_dir / "apihooks.log", "w", encoding="utf-8", buffering=1)
+    _cli_fh   = open(_session_dir / "clicalls.log", "w", encoding="utf-8", buffering=1)
 
-    _tool_fh.write(f"# Tool-call log — session {_ts}\n\n")
+    _tool_fh.write(f"# Tool-call log — session {_session_id}\n\n")
     _tool_fh.flush()
-    _cli_fh.write(f"# CLI Subprocess Call Log — session {_ts}\n\n") # Header for new log file
+    _cli_fh.write(f"# CLI Subprocess Call Log — session {_session_id}\n\n")
     _cli_fh.flush()
 
+    # Register this session in the log registry
+    try:
+        from log_registry import LogRegistry
+        registry = LogRegistry(str(_LOG_DIR / "log_registry.toml"))
+        registry.register_session(_session_id, str(_session_dir), datetime.datetime.now())
+    except Exception as e:
+        print(f"Warning: Could not register session in LogRegistry: {e}")
+
     atexit.register(close_session)
 
 

tests/test_session_logging.py

@@ -0,0 +1,58 @@
+import os
+import shutil
+import pytest
+from pathlib import Path
+from datetime import datetime
+from unittest.mock import patch
+import session_logger
+import tomllib
+
+@pytest.fixture
+def temp_logs(tmp_path):
+    # Mock _LOG_DIR in session_logger
+    original_log_dir = session_logger._LOG_DIR
+    session_logger._LOG_DIR = tmp_path / "logs"
+    session_logger._LOG_DIR.mkdir(parents=True, exist_ok=True)
+    
+    # Mock _SCRIPTS_DIR
+    original_scripts_dir = session_logger._SCRIPTS_DIR
+    session_logger._SCRIPTS_DIR = tmp_path / "scripts" / "generated"
+    session_logger._SCRIPTS_DIR.mkdir(parents=True, exist_ok=True)
+    
+    yield tmp_path / "logs"
+    
+    # Cleanup: Close handles if open
+    session_logger.close_session()
+    session_logger._LOG_DIR = original_log_dir
+    session_logger._SCRIPTS_DIR = original_scripts_dir
+
+def test_open_session_creates_subdir_and_registry(temp_logs):
+    label = "test-label"
+    # We can't easily mock datetime.datetime.now() because it's a built-in
+    # but we can check the resulting directory name pattern
+    
+    session_logger.open_session(label=label)
+    
+    # Check that a subdirectory was created
+    subdirs = list(temp_logs.iterdir())
+    # One is the log_registry.toml, one is the session dir
+    session_dirs = [d for d in subdirs if d.is_dir()]
+    assert len(session_dirs) == 1
+    session_dir = session_dirs[0]
+    
+    assert session_dir.name.endswith(f"_{label}")
+    
+    # Check for log files
+    assert (session_dir / "comms.log").exists()
+    assert (session_dir / "toolcalls.log").exists()
+    assert (session_dir / "apihooks.log").exists()
+    assert (session_dir / "clicalls.log").exists()
+    
+    # Check registry
+    registry_path = temp_logs / "log_registry.toml"
+    assert registry_path.exists()
+    
+    with open(registry_path, "rb") as f:
+        data = tomllib.load(f)
+        assert session_dir.name in data
+        assert data[session_dir.name]["path"] == str(session_dir)