diff --git a/plexpy/__init__.py b/plexpy/__init__.py
index 3d53816d..3005597d 100644
--- a/plexpy/__init__.py
+++ b/plexpy/__init__.py
@@ -15,6 +15,7 @@
 
 import os
 from Queue import Queue
+import shutil
 import sqlite3
 import sys
 import subprocess
@@ -156,6 +157,16 @@ def initialize(config_file):
             except OSError as e:
                 logger.error(u"Could not create cache dir '%s': %s" % (CONFIG.CACHE_DIR, e))
 
+        if CONFIG.CACHE_DIR:
+            session_metadata_folder = os.path.join(CONFIG.CACHE_DIR, 'session_metadata')
+            try:
+                shutil.rmtree(session_metadata_folder, ignore_errors=True)
+            except OSError as e:
+                pass
+
+            if not os.path.exists(session_metadata_folder):
+                os.mkdir(session_metadata_folder)
+
         # Initialize the database
         logger.info(u"Checking if the database upgrades are required...")
         try:
diff --git a/plexpy/activity_handler.py b/plexpy/activity_handler.py
index 6f51f3e0..96f3ed1e 100644
--- a/plexpy/activity_handler.py
+++ b/plexpy/activity_handler.py
@@ -546,7 +546,7 @@ def on_created(rating_key, **kwargs):
 
 def delete_metadata_cache(session_key):
     try:
-        os.remove(os.path.join(plexpy.CONFIG.CACHE_DIR, 'metadata-sessionKey-%s.json' % session_key))
+        os.remove(os.path.join(plexpy.CONFIG.CACHE_DIR, 'session_metadata/metadata-sessionKey-%s.json' % session_key))
     except IOError as e:
         logger.error(u"Tautulli ActivityHandler :: Failed to remove metadata cache file (sessionKey %s): %s"
                      % (session_key, e))
diff --git a/plexpy/pmsconnect.py b/plexpy/pmsconnect.py
index cd17ba98..5f23a7a0 100644
--- a/plexpy/pmsconnect.py
+++ b/plexpy/pmsconnect.py
@@ -533,7 +533,7 @@ class PmsConnect(object):
         metadata = {}
 
         if cache_key:
-            in_file_path = os.path.join(plexpy.CONFIG.CACHE_DIR, 'metadata-sessionKey-%s.json' % cache_key)
+            in_file_path = os.path.join(plexpy.CONFIG.CACHE_DIR, 'session_metadata/metadata-sessionKey-%s.json' % cache_key)
             try:
                 with open(in_file_path, 'r') as inFile:
                     metadata = json.load(inFile)
@@ -1179,7 +1179,7 @@ class PmsConnect(object):
             if cache_key:
                 metadata['_cache_time'] = int(time.time())
 
-                out_file_path = os.path.join(plexpy.CONFIG.CACHE_DIR, 'metadata-sessionKey-%s.json' % cache_key)
+                out_file_path = os.path.join(plexpy.CONFIG.CACHE_DIR, 'session_metadata/metadata-sessionKey-%s.json' % cache_key)
                 try:
                     with open(out_file_path, 'w') as outFile:
                         json.dump(metadata, outFile)