Server Version#: 1.22.3.4392
Player Version#: 7.16
Got the same issue as https://forums.plex.tv/t/shared-library-disapears-from-user-when-attempting-to-access/641899
When the user connects, the shared libraries disappears from the server config.
From the other thread:
Go ahead and invite them again and have them accept the share. Then PM me their email address so I can check that the invite is linked properly between your accounts.
Any Plex employee who can check the same for me?
Which client type does the shared user, erm, use?
Could you ask the sharee to use the web app first, after you re-established the share?
https://app.plex.tv
I am trying to determine whether this is something connected to the iOS app specifically.
He told me that he had tested with several clients, but I will re-enable the share, and have him test again.
Re-established the share. Connected with the web-ui first time, and the share checkbox is empty again 
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Is this still an issue?
