diff --git a/data/interfaces/default/newsletter_config.html b/data/interfaces/default/newsletter_config.html
index 21577380..c198e46a 100644
--- a/data/interfaces/default/newsletter_config.html
+++ b/data/interfaces/default/newsletter_config.html
@@ -2,6 +2,7 @@
 <%!
     import json
     from plexpy import helpers, notifiers
+    from plexpy.notification_handler import PILLOW
 
     email_notifiers = [n for n in notifiers.get_notifiers() if n['agent_name'] == 'email']
     sorted(email_notifiers, key=lambda k: (k['agent_label'], k['friendly_name'], k['id']))
diff --git a/plexpy/__init__.py b/plexpy/__init__.py
index 37bd13a5..f4f5232f 100644
--- a/plexpy/__init__.py
+++ b/plexpy/__init__.py
@@ -478,6 +478,7 @@ def start():
             analytics_event(category='system', action='start')
 
         # Schedule newsletters
+        newsletter_handler.NEWSLETTER_SCHED.start()
         newsletter_handler.schedule_newsletters()
 
         _STARTED = True
diff --git a/plexpy/newsletter_handler.py b/plexpy/newsletter_handler.py
index cffd59a3..9a5842ea 100644
--- a/plexpy/newsletter_handler.py
+++ b/plexpy/newsletter_handler.py
@@ -28,41 +28,25 @@ NEWSLETTER_SCHED = BackgroundScheduler()
 
 
 def schedule_newsletters(newsletter_id=None):
-    with plexpy.SCHED_LOCK:
+    newsletters_list = newsletters.get_newsletters(newsletter_id=newsletter_id)
 
-        # Check if scheduler should be started
-        start_jobs = not len(NEWSLETTER_SCHED.get_jobs())
+    for newsletter in newsletters_list:
+        newsletter_job_name = '{} ({})'.format(newsletter['agent_label'],
+                                               newsletter['friendly_name'] or newsletter['id'])
 
-        newsletters_list = newsletters.get_newsletters(newsletter_id=newsletter_id)
-
-        for newsletter in newsletters_list:
-            newsletter_job_name = '{} ({})'.format(newsletter['agent_label'],
-                                                   newsletter['friendly_name'] or newsletter['id'])
-
-            if newsletter['active']:
-                keys = ['minute', 'hour', 'day', 'month', 'day_of_week']
-                values = newsletter['cron'].split()
-                cron = {k: v for k, v in zip(keys, values)}
-
-                schedule_newsletter_job('newsletter-{}'.format(newsletter['id']), name=newsletter_job_name,
-                                        func=notify, args=[newsletter['id'], 'on_cron'], cron=newsletter['cron'])
-            else:
-                schedule_newsletter_job('newsletter-{}'.format(newsletter['id']), name=newsletter_job_name,
-                                        remove_job=True)
-
-        # Start scheduler
-        if start_jobs and len(NEWSLETTER_SCHED.get_jobs()):
-            try:
-                NEWSLETTER_SCHED.start()
-            except Exception as e:
-                logger.error(e)
+        if newsletter['active']:
+            schedule_newsletter_job('newsletter-{}'.format(newsletter['id']), name=newsletter_job_name,
+                                    func=notify, args=[newsletter['id'], 'on_cron'], cron=newsletter['cron'])
+        else:
+            schedule_newsletter_job('newsletter-{}'.format(newsletter['id']), name=newsletter_job_name,
+                                    remove_job=True)
 
 
 def schedule_newsletter_job(newsletter_job_id, name='', func=None, remove_job=False, args=None, cron=None):
     if NEWSLETTER_SCHED.get_job(newsletter_job_id):
         if remove_job:
             NEWSLETTER_SCHED.remove_job(newsletter_job_id)
-            logger.info(u"Tautulli NewsletterHandler :: Removed newsletter schedule: %s" % newsletter_job_id)
+            logger.info(u"Tautulli NewsletterHandler :: Removed scheduled newsletter: %s" % name)
         else:
             NEWSLETTER_SCHED.reschedule_job(
                 newsletter_job_id, args=args, trigger=CronTrigger().from_crontab(cron))
diff --git a/plexpy/newsletters.py b/plexpy/newsletters.py
index 6a0b14dc..b5589ec1 100644
--- a/plexpy/newsletters.py
+++ b/plexpy/newsletters.py
@@ -587,4 +587,19 @@ class RecentlyAdded(Newsletter):
                           }
                          ]
 
+        if not PILLOW:
+            pillow_message = {
+                'label': 'Background Art',
+                'description': 'The Pillow library is missing. '
+                               'Background art on the newsletter media cards will not be included.<br>'
+                               'Install the Pillow library to add background art. '
+                               'Instructions can be found in the '
+                               '<a href="' + helpers.anon_url('https://github.com/%s/plexpy/wiki/'
+                                                              'Frequently-Asked-Questions-(FAQ)#notifications-pillow'
+                                                              % plexpy.CONFIG.GIT_USER) + '" target="_blank">FAQ</a>.',
+                'name': 'recently_added_pillow',
+                'input_type': 'help'
+                }
+            config_option.insert(0, pillow_message)
+
         return config_option