diff --git a/resources/lib/kodimonitor.py b/resources/lib/kodimonitor.py
index 102df474..0bebae33 100644
--- a/resources/lib/kodimonitor.py
+++ b/resources/lib/kodimonitor.py
@@ -209,18 +209,24 @@ class KodiMonitor(Monitor):
         # Kodi remembers the last setResolvedUrl - which is empty in our case
         kodi_item = js.get_item(data['playlistid'])
         LOG.debug('kodi_item: %s', kodi_item)
-        # if kodi_item.get('file') == '':
-        #     LOG.info('Detected re-start of playback of last item')
-        #     old = state.OLD_PLAYER_STATES[data['playlistid']]
-        #     kwargs = {
-        #         'plex_id': old['plex_id'],
-        #         'plex_type': old['plex_type'],
-        #         'path': old['file'],
-        #         'resolve': False
-        #     }
-        #     thread = Thread(target=playback_triage, kwargs=kwargs)
-        #     thread.start()
-        #     return
+        if (state.RESUMABLE is True and
+                data['position'] == 0 and
+                data['item'].get('title') is not None and
+                getCondVisibility('Window.IsVisible(MyVideoNav.xml)')):
+            # Hack we need for RESUMABLE items because Kodi lost the path of the
+            # last played item that is now being replayed (see playback.py's
+            # Player().play())
+            LOG.info('Detected re-start of playback of last item')
+            old = state.OLD_PLAYER_STATES[data['playlistid']]
+            kwargs = {
+                'plex_id': old['plex_id'],
+                'plex_type': old['plex_type'],
+                'path': old['file'],
+                'resolve': False
+            }
+            thread = Thread(target=playback_triage, kwargs=kwargs)
+            thread.start()
+            return
         # Have we initiated the playqueue already? If not, ignore this
         if not playqueue.items:
             LOG.debug('Playqueue not initiated - ignoring')
@@ -414,6 +420,8 @@ class SpecialMonitor(Thread):
             if (not is_playing and
                     getCondVisibility('Window.IsVisible(DialogContextMenu.xml)') and
                     getInfoLabel('Control.GetLabel(1002)') == getLocalizedString(12021)):
+                # Remember that the item IS indeed resumable
+                state.RESUMABLE = True
                 control = int(Window(10106).getFocusId())
                 if control == 1002:
                     # Start from beginning
diff --git a/resources/lib/playback.py b/resources/lib/playback.py
index 5cb3b221..d6d05219 100644
--- a/resources/lib/playback.py
+++ b/resources/lib/playback.py
@@ -173,6 +173,12 @@ def playback_init(plex_id, plex_type, playqueue):
                     args=(playqueue.kodi_pl, ))
     thread.setDaemon(True)
     LOG.info('Done initializing PKC playback, starting Kodi player')
+    # By design, PKC will start Kodi playback using Player().play(). Kodi
+    # caches paths like our plugin://pkc. If we use Player().play() between
+    # 2 consecutive startups of exactly the same Kodi library item, Kodi's
+    # cache will have been flushed for some reason. Hence the 2nd call for
+    # plugin://pkc will be lost; Kodi will try to startup playback for an empty
+    # path: log entry is "CGUIWindowVideoBase::OnPlayMedia <missing path>"
     thread.start()
 
 
@@ -287,6 +293,8 @@ def conclude_playback(playqueue, pos):
         LOG.info('Resuming playback at %s', item.offset)
         listitem.setProperty('StartOffset', str(item.offset))
         listitem.setProperty('resumetime', str(item.offset))
+    # Reset the resumable flag
+    state.RESUMABLE = False
     result.listitem = listitem
     pickle_me(result)
     LOG.info('Done concluding playback')
diff --git a/resources/lib/state.py b/resources/lib/state.py
index c2a99e09..50578541 100644
--- a/resources/lib/state.py
+++ b/resources/lib/state.py
@@ -134,6 +134,8 @@ PLAYSTATE = {
 # paths for playback (since we're not receiving a Kodi id)
 PLEX_IDS = {}
 PLAYED_INFO = {}
+# Flag whether Kodi item where the playback is being started is even resumable
+RESUMABLE = False
 # Set by SpecialMonitor - did user choose to resume playback or start from the
 # beginning?
 RESUME_PLAYBACK = False