diff --git a/djblets/log/__init__.py b/djblets/log/__init__.py
--- a/djblets/log/__init__.py
+++ b/djblets/log/__init__.py
@@ -28,6 +28,12 @@
 from datetime import datetime
 import logging
 import os
+import sys
+
+try:
+    from logging import WatchedFileHandler
+except ImportError:
+    from djblets.log.handlers import WatchedFileHandler
 
 from django.conf import settings
 
@@ -101,12 +107,17 @@ def init_logging():
     log_path = os.path.join(log_directory, log_name + ".log")
 
     try:
-        logging.basicConfig(
-            level=log_level,
-            format=format_str,
-            filename=log_path,
-            filemode='a'
-        )
+        if sys.platform == 'win32':
+            handler = logging.FileHandler(log_path)
+        else:
+            handler = WatchedFileHandler(log_path)
+
+        handler.setLevel(log_level)
+        handler.setFormatter(logging.Formatter(format_str))
+
+        root = logging.getLogger('')
+        root.addHandler(handler)
+        root.setLevel(log_level)
     except IOError:
         logging.basicConfig(
             level=log_level,
@@ -140,8 +151,14 @@ def init_profile_logger():
 
     if (enabled and log_directory and log_name and not _profile_log and
         getattr(settings, "LOGGING_ALLOW_PROFILING", False)):
-        handler = logging.FileHandler(
-            os.path.join(log_directory, log_name + ".prof"))
+
+        filename = os.path.join(log_directory, log_name + ".prof")
+
+        if sys.platform == 'win32':
+            handler = logging.FileHandler(filename)
+        else:
+            handler = WatchedFileHandler(filename)
+
         handler.setLevel(logging.INFO)
         handler.setFormatter(logging.Formatter("%(asctime)s %(message)s"))
 
diff --git a/djblets/log/handlers.py b/djblets/log/handlers.py
--- /dev/null
+++ b/djblets/log/handlers.py
@@ -0,0 +1,85 @@
+#
+# handlers.py -- Custom logging handlers
+#
+# Copyright (c) 2010  Christian Hammond
+#
+# Permission is hereby granted, free of charge, to any person obtaining
+# a copy of this software and associated documentation files (the
+# "Software"), to deal in the Software without restriction, including
+# without limitation the rights to use, copy, modify, merge, publish,
+# distribute, sublicense, and/or sell copies of the Software, and to
+# permit persons to whom the Software is furnished to do so, subject to
+# the following conditions:
+#
+# The above copyright notice and this permission notice shall be included
+# in all copies or substantial portions of the Software.
+#
+# THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND,
+# EXPRESS OR IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF
+# MERCHANTABILITY, FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT.
+# IN NO EVENT SHALL THE AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY
+# CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN AN ACTION OF CONTRACT,
+# TORT OR OTHERWISE, ARISING FROM, OUT OF OR IN CONNECTION WITH THE
+# SOFTWARE OR THE USE OR OTHER DEALINGS IN THE SOFTWARE.
+#
+
+import logging
+import os
+from stat import ST_DEV, ST_INO
+
+
+# This is a port of Python 2.6's WatchedFileHandler. It should only be
+# used if logging.handlers.WatchedFileHandler can't be imported.
+#
+# This class is copyright by the Python Software Foundation.
+# See http://www.python.org/psf/license/ for details.
+class WatchedFileHandler(logging.FileHandler):
+    """
+    A handler for logging to a file, which watches the file
+    to see if it has changed while in use. This can happen because of
+    usage of programs such as newsyslog and logrotate which perform
+    log file rotation. This handler, intended for use under Unix,
+    watches the file to see if it has changed since the last emit.
+    (A file has changed if its device or inode have changed.)
+    If it has changed, the old file stream is closed, and the file
+    opened to get a new stream.
+
+    This handler is not appropriate for use under Windows, because
+    under Windows open files cannot be moved or renamed - logging
+    opens the files with exclusive locks - and so there is no need
+    for such a handler. Furthermore, ST_INO is not supported under
+    Windows; stat always returns zero for this value.
+
+    This handler is based on a suggestion and patch by Chad J.
+    Schroeder.
+    """
+    def __init__(self, filename, mode='a', encoding=None, delay=0):
+        logging.FileHandler.__init__(self, filename, mode, encoding, delay)
+        if not os.path.exists(self.baseFilename):
+            self.dev, self.ino = -1, -1
+        else:
+            stat = os.stat(self.baseFilename)
+            self.dev, self.ino = stat[ST_DEV], stat[ST_INO]
+
+    def emit(self, record):
+        """
+        Emit a record.
+
+        First check if the underlying file has changed, and if it
+        has, close the old stream and reopen the file to get the
+        current stream.
+        """
+        if not os.path.exists(self.baseFilename):
+            stat = None
+            changed = 1
+        else:
+            stat = os.stat(self.baseFilename)
+            changed = (stat[ST_DEV] != self.dev) or (stat[ST_INO] != self.ino)
+        if changed and self.stream is not None:
+            self.stream.flush()
+            self.stream.close()
+            self.stream = self._open()
+            if stat is None:
+                stat = os.stat(self.baseFilename)
+            self.dev, self.ino = stat[ST_DEV], stat[ST_INO]
+        logging.FileHandler.emit(self, record)