Plex Shares

Not sure if i’m posting in correct place as this is my first issue with plex. (Apologies in advance)
I tried to share a single episode with a friend by going to the episode, right click it, chhose share, choose friend to share with.
He can see the episode but gets a playback error every time
If i create a Test folder under TV Shows and add the episode into that folder and share that folder he can see it and it plays fine
I used to be able to just right click an episode and use share without a folder and it worked fine
What am i doing wrong or has something changed?
I recently reinstalled plex on my Synology Nas
I am a PLEX PASS user and the version of plex on my nas is Version 1.35.1.2632-c6783c78
Any/all help is very much appreciated
Emails just in case: EMAIL REDACTED - Privacy
Thank you

@lacrymosa1

Have your friend try it again.

When the failure occurs, you now grab your server logs (settings - server - troubleshooting - download logs)

It will give you a ZIP file.

Please attach that here. (give it time to upload & attach before hitting reply)

I will look at it.

I’ve edited the email above for privacy.

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