diff --git a/tests/test_logging_e2e.py b/tests/test_logging_e2e.py
new file mode 100644
index 0000000..e26fc1e
--- /dev/null
+++ b/tests/test_logging_e2e.py
@@ -0,0 +1,73 @@
+import os
+import shutil
+import pytest
+from pathlib import Path
+from datetime import datetime, timedelta
+from unittest.mock import patch
+import session_logger
+import tomllib
+from log_registry import LogRegistry
+from log_pruner import LogPruner
+
+@pytest.fixture
+def e2e_setup(tmp_path):
+    # Mock _LOG_DIR and _SCRIPTS_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)
+    
+    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
+    
+    # Cleanup
+    session_logger.close_session()
+    session_logger._LOG_DIR = original_log_dir
+    session_logger._SCRIPTS_DIR = original_scripts_dir
+
+def test_logging_e2e(e2e_setup):
+    tmp_path = e2e_setup
+    logs_dir = tmp_path / "logs"
+
+    # Step 1: Initialize (open_session)
+    session_logger.open_session(label="E2E_Test")
+    session_id = session_logger._session_id
+    session_dir = session_logger._session_dir
+
+    # Step 2: Simulate logs (write 'ERROR' to 'comms.log')
+    # Use log_comms which writes to comms.log
+    session_logger.log_comms({"level": "ERROR", "message": "Something went wrong"})
+
+    # Step 3: Shutdown (close_session)
+    session_logger.close_session()
+
+    # Step 4: Verify 'log_registry.toml' has the session whitelisted due to 'ERROR'
+    registry_path = logs_dir / "log_registry.toml"
+    registry = LogRegistry(str(registry_path))
+    assert registry.is_session_whitelisted(session_id), "Current session should be whitelisted due to ERROR keyword"
+
+    # Step 5: Simulate an OLD insignificant session in the registry and directory
+    old_session_id = "20200101_120000_OLD"
+    old_session_dir = logs_dir / old_session_id
+    old_session_dir.mkdir()
+    (old_session_dir / "comms.log").write_text("nothing special") # < 2KB
+
+    old_start_time = datetime.now() - timedelta(days=2)
+    registry.register_session(old_session_id, str(old_session_dir), old_start_time)
+
+    # Step 6: Trigger 'LogPruner.prune()'
+    pruner = LogPruner(registry, str(logs_dir))
+    pruner.prune()
+
+    # Step 7: Verify the OLD session is deleted but the NEW (whitelisted) session is kept.
+    assert not old_session_dir.exists(), "Old insignificant session should have been pruned"
+    assert session_dir.exists(), "New whitelisted session should have been kept"
+
+    # Extra check: Whitelisted sessions should be kept even if old
+    # Manually backdate the current session
+    registry.data[session_id]['start_time'] = (datetime.now() - timedelta(days=2)).isoformat()
+    registry.save_registry()
+    pruner.prune()
+    assert session_dir.exists(), "Whitelisted session should be kept even if it is old and small"