diff --git a/python_apps/pypo/pypofetch.py b/python_apps/pypo/pypofetch.py
index 1dbe97070..de76a4ca0 100644
--- a/python_apps/pypo/pypofetch.py
+++ b/python_apps/pypo/pypofetch.py
@@ -171,8 +171,8 @@ class PypoFetch(Thread):
         self.logger.debug('Getting information needed on bootstrap from Airtime')
         info = self.api_client.get_bootstrap_info()
         if info == None:
-            self.logger.error('Unable to get bootstrap info.. Existing pypo...')
-            sys.exit(0)
+            self.logger.error('Unable to get bootstrap info.. Exiting pypo...')
+            sys.exit(1)
         else:
             self.logger.debug('info:%s', info)
             for k, v in info['switch_status'].iteritems():
@@ -427,6 +427,7 @@ class PypoFetch(Thread):
                     fileExt = os.path.splitext(media_item['uri'])[1]
                     dst = os.path.join(download_dir, media_item['id'] + fileExt)
                     media_item['dst'] = dst
+                    media_item['started_copying'] = False
                     media_filtered[key] = media_item
 
             self.media_prepare_queue.put(copy.copy(media_filtered))
diff --git a/python_apps/pypo/pypofile.py b/python_apps/pypo/pypofile.py
index 81a48b96d..6f9a213e6 100644
--- a/python_apps/pypo/pypofile.py
+++ b/python_apps/pypo/pypofile.py
@@ -70,6 +70,9 @@ class PypoFile(Thread):
         if do_copy:
             self.logger.debug("copying from %s to local cache %s" % (src, dst))
             try:
+
+                media_item['started_copying'] = True
+
                 """
                 copy will overwrite dst if it already exists
                 """
diff --git a/python_apps/pypo/pypopush.py b/python_apps/pypo/pypopush.py
index 9cac4022c..03420b9d9 100644
--- a/python_apps/pypo/pypopush.py
+++ b/python_apps/pypo/pypopush.py
@@ -80,8 +80,7 @@ class PypoPush(Thread):
                     self.modify_cue_point(current_event_chain[0])
                     next_media_item_chain = current_event_chain
                     time_until_next_play = 0
-                    #sleep for 0.2 seconds to give pypo-file time to copy. This is a quick
-                    #fix that will be improved in 2.1.1
+                    #sleep for 0.2 seconds to give pypo-file time to copy.
                     time.sleep(0.2)
                 else:
                     media_chain = filter(lambda item: (item["type"] == "file"), current_event_chain)
@@ -313,7 +312,20 @@ class PypoPush(Thread):
         try:
             for media_item in event_chain:
                 if media_item['type'] == "file":
-                    self.telnet_to_liquidsoap(media_item)
+
+                    """
+                    Wait maximum 5 seconds (50 iterations) for file to become ready, otherwise
+                    give up on it.
+                    """
+                    iter_num = 0
+                    while not media_item['started_copying'] and iter_num < 50:
+                        time.sleep(0.1)
+                        iter_num += 1
+
+                    if media_item['started_copying']:
+                        self.telnet_to_liquidsoap(media_item)
+                    else:
+                        self.logger.warn("File %s did not become ready in less than 5 seconds. Skipping...", media_item['dst'])
                 elif media_item['type'] == "event":
                     if media_item['event_type'] == "kick_out":
                         PypoFetch.disconnect_source(self.logger, self.telnet_lock, "live_dj")