diff --git a/src/dippy/dippy.py b/src/dippy/dippy.py
index eb069da..c08624f 100644
--- a/src/dippy/dippy.py
+++ b/src/dippy/dippy.py
@@ -20,6 +20,7 @@
 import sys
 from pathlib import Path
 
+from dippy.core.analyzer import analyze
 from dippy.core.config import (
     Config,
     ConfigError,
@@ -29,8 +30,6 @@
     match_after_mcp,
     match_mcp,
 )
-from dippy.core.analyzer import analyze
-
 
 # === Mode Detection ===
 
@@ -86,17 +85,23 @@ def _get_log_file() -> Path:
     return Path.home() / ".claude" / "hook-approvals.log"
 
 
+_LOG_FORMAT = "%(asctime)s [%(levelname)s] %(message)s"
+_LOG_DATEFMT = "%Y-%m-%d %H:%M:%S"
+
+
 def setup_logging():
-    """Configure logging to file. Fails silently if unable to write."""
+    """Add a file handler for the detected mode's log directory.
+
+    Called after mode is finalized so the log file goes to the correct
+    directory (~/.claude/, ~/.cursor/, etc.). Fails silently.
+    """
     try:
         log_file = _get_log_file()
         log_file.parent.mkdir(parents=True, exist_ok=True)
-        logging.basicConfig(
-            filename=str(log_file),
-            level=logging.INFO,
-            format="%(asctime)s [%(levelname)s] %(message)s",
-            datefmt="%Y-%m-%d %H:%M:%S",
-        )
+        handler = logging.FileHandler(str(log_file))
+        handler.setLevel(logging.INFO)
+        handler.setFormatter(logging.Formatter(_LOG_FORMAT, datefmt=_LOG_DATEFMT))
+        logging.getLogger().addHandler(handler)
     except (OSError, PermissionError):
         pass  # Logging is optional - don't crash if we can't write
 
@@ -304,7 +309,8 @@ def main():
         print("Run 'dippy --help' for usage.")
         raise SystemExit(0)
 
-    setup_logging()
+    # Stderr fallback so early errors (bad JSON, unknown tool) are visible
+    logging.basicConfig(level=logging.INFO, format=_LOG_FORMAT, datefmt=_LOG_DATEFMT)
 
     try:
         # Read hook input from stdin
@@ -313,6 +319,11 @@ def main():
         # Auto-detect mode from input if no explicit flag/env was set
         if _EXPLICIT_MODE is None:
             MODE = _detect_mode_from_input(input_data)
+
+        # Add file handler now that mode (and thus log directory) is known
+        setup_logging()
+
+        if _EXPLICIT_MODE is None:
             logging.info(f"Auto-detected mode: {MODE}")
 
         # Extract cwd from input