Server Version#: 1.41.0.8992
Player Version#: 1.103.1.238-223cbba6
This issue has been around for at least a year that I can personally remember dealing with it.
It’s described in several threads that had no adequate response and were closed automatically because of a 90 day timeout. Here’s an example response that describes the situation: Increase amount of continue watching on home screen? - #9 by amcdon
In short, after using the Plex for Windows client (leaving it open in the background between sessions) it will eventually reduce the Continue Watching list to 3 or 4 titles. Any new title added will be appended to the front of the list and the last one will disappear.
They are NOT removed from Continue Watching. The titles appear on other clients correctly. Further, when I restart Plex for Windows, they all come back.
My “Weeks to consider” is set to 12 - I can’t remember if that’s the default or if I changed it, but if I did, it was a long time ago.
My “Maximum number of items” is set to 15.
“Include season premieres” is checked.
No actions in the player will reset the Continue Watching issue as far as I’ve been able to determine. Only restarting the client works.