diff --git a/redstring/__init__.py b/redstring/__init__.py
index 9a47f98..075e50d 100644
--- a/redstring/__init__.py
+++ b/redstring/__init__.py
@@ -1,2 +1,14 @@
+import logging
+
 import redstring.parser
-import redstring.server
\ No newline at end of file
+import redstring.server
+
+formatter = logging.Formatter('[{asctime}] [{process}] [{levelname}] {message}', '%Y-%m-%d %H:%M:%S %z', style='{')
+
+handler = logging.StreamHandler()
+handler.setFormatter(formatter)
+handler.setLevel(logging.DEBUG)
+
+logger = logging.getLogger(__name__)
+logger.setLevel(logging.DEBUG)
+logger.addHandler(handler)
diff --git a/redstring/server.py b/redstring/server.py
index a62baf4..6be5a28 100644
--- a/redstring/server.py
+++ b/redstring/server.py
@@ -3,6 +3,7 @@ Logic for serving a collection of documents through a web frontend.
 """
 import argparse
 import json
+import logging
 import os
 import random
 import string
@@ -47,6 +48,8 @@ class LoginForm(FlaskForm):
 
 CONFIG_ENVVAR = 'REDSTRING_CONFIG'
 
+logger = logging.getLogger(__name__)
+
 app = Flask(__name__)
 app.secret_key = ''.join(random.choices(string.ascii_uppercase + string.digits, k=32))
 
@@ -60,10 +63,16 @@ def check_password(app, password):
     Checks if a password is correct
     """
     password_file = app.config['password_file']
+    if not os.path.isfile(password_file):
+        logger.debug('Authentication failed: no password file found')
     with open(password_file) as f:
         real_password = f.read().strip()
     correct = password == real_password
     del real_password
+    if correct:
+        logger.debug('Authentication successful')
+    else:
+        logger.debug('Authentication failed: password incorrect')
     return correct
 
 
@@ -223,4 +232,6 @@ def cli():
 def wsgi():
     config_path = os.environ.get(CONFIG_ENVVAR) or '/etc/redstring.conf'
     config = read_config(app, config_path)
+    logger.setLevel(logging.DEBUG)
+    logger.debug(f'Loaded config from {config_path}: {config}')
     return app