Continue Watching is buggy? Unable to figure out why

Ahh ok that makes sense then. Continue Watching looks at Watch State and Watch History. With the recent change in PMS, only actual watching will create Watch History AND update the Watch State thus moving that show and it’s episodes into On Deck and Continue Watching. Because your show and episodes only had a Watch State change to Watched and no Watch History it won’t be in Continue Watching.

This was added in 1.40.0 :

  • (View History) No longer create a view history entry for items marked as played (#10888)