diff --git a/plexpy/__init__.py b/plexpy/__init__.py
index 876c5147..9809d18e 100644
--- a/plexpy/__init__.py
+++ b/plexpy/__init__.py
@@ -412,7 +412,7 @@ def dbcheck():
         'audio_channels INTEGER, transcode_protocol TEXT, transcode_container TEXT, '
         'transcode_video_codec TEXT, transcode_audio_codec TEXT, transcode_audio_channels INTEGER,'
         'transcode_width INTEGER, transcode_height INTEGER, buffer_count INTEGER DEFAULT 0, '
-        'buffer_last_triggered INTEGER, last_paused INTEGER)'
+        'buffer_last_triggered INTEGER, last_paused INTEGER, write_attempts INTEGER DEFAULT 0)'
     )
 
     # session_history table :: This is a history table which logs essential stream details
@@ -653,6 +653,15 @@ def dbcheck():
             'ALTER TABLE sessions ADD COLUMN transcode_key TEXT'
         )
 
+    # Upgrade sessions table from earlier versions
+    try:
+        c_db.execute('SELECT write_attempts FROM sessions')
+    except sqlite3.OperationalError:
+        logger.debug(u"Altering database. Updating database table sessions.")
+        c_db.execute(
+            'ALTER TABLE sessions ADD COLUMN write_attempts INTEGER DEFAULT 0'
+        )
+
     # Upgrade session_history table from earlier versions
     try:
         c_db.execute('SELECT reference_id FROM session_history')
diff --git a/plexpy/activity_pinger.py b/plexpy/activity_pinger.py
index 3206dd76..6a9ba8b1 100644
--- a/plexpy/activity_pinger.py
+++ b/plexpy/activity_pinger.py
@@ -206,8 +206,24 @@ def check_active_sessions(ws_request=False):
                         monitor_db.action('DELETE FROM sessions WHERE session_key = ? AND rating_key = ?',
                                           [stream['session_key'], stream['rating_key']])
                     else:
-                        logger.warn(u"PlexPy Monitor :: Failed to write sessionKey %s ratingKey %s to the database. " \
-                                    "Will try again on the next pass." % (stream['session_key'], stream['rating_key']))
+                        stream['write_attempts'] += 1
+
+                        if stream['write_attempts'] < plexpy.CONFIG.SESSION_DB_WRITE_ATTEMPTS:
+                            logger.warn(u"PlexPy Monitor :: Failed to write sessionKey %s ratingKey %s to the database. " \
+                                        "Will try again on the next pass. Write attempt %s."
+                                        % (stream['session_key'], stream['rating_key'], str(stream['write_attempts'])))
+                            monitor_db.action('UPDATE sessions SET write_attempts = ? '
+                                              'WHERE session_key = ? AND rating_key = ?',
+                                              [stream['write_attempts'], stream['session_key'], stream['rating_key']])
+                        else:
+                            logger.warn(u"PlexPy Monitor :: Failed to write sessionKey %s ratingKey %s to the database. " \
+                                        "Removing session from the database. Write attempt %s."
+                                        % (stream['session_key'], stream['rating_key'], str(stream['write_attempts'])))
+                            logger.debug(u"PlexPy Monitor :: Removing sessionKey %s ratingKey %s from session queue"
+                                         % (stream['session_key'], stream['rating_key']))
+                            monitor_db.action('DELETE FROM sessions WHERE session_key = ? AND rating_key = ?',
+                                              [stream['session_key'], stream['rating_key']])
+
 
             # Process the newly received session data
             for session in media_container:
diff --git a/plexpy/config.py b/plexpy/config.py
index bb03fdf3..d53e8554 100644
--- a/plexpy/config.py
+++ b/plexpy/config.py
@@ -374,6 +374,7 @@ _CONFIG_DEFINITIONS = {
     'REFRESH_LIBRARIES_ON_STARTUP': (int, 'Monitoring', 1),
     'REFRESH_USERS_INTERVAL': (int, 'Monitoring', 12),
     'REFRESH_USERS_ON_STARTUP': (int, 'Monitoring', 1),
+    'SESSION_DB_WRITE_ATTEMPTS': (int, 'Monitoring', 5),
     'SLACK_ENABLED': (int, 'Slack', 0),
     'SLACK_HOOK': (str, 'Slack', ''),
     'SLACK_CHANNEL': (str, 'Slack', ''),