For the past few days Plex scrobler more often doesn’t work than it does. On Plex Server side nothing changed and I double-checked webhook and notification settings. Restarted the server to be sure, but it still doesn’t work. There was a short period of time I noticed yesterday when it worked and content was marked as watched, but now again it doesn’t…
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It seems that since at least around 16 hours ago it started working again without any issues. I hope it stays the same 
But for the past week there were cases when it worked and then stopped again
Having a similar issue. All of the sudden Plex does not scrobble on my Chromebook but it does on my Android phone. Nothing has changed on the Chromebook and there hasn’t been a Plex update since the 27th.