@pixr - Sorry for the delayed response. I was traveling, back home now.
iPhone 12Pro running iOS 14.X (wifi turned off)
2015 15in MBP
What works for me (using just the Tailscale IP):
Everything seems similar.
The image confirms the question around using https and the https toggle (which is how it has been)…
I have iOS Files > Shared Location > Synology IP connected and showing as you have above (to 5006.)
BUT, selecting that location brings up a an empty page showing - items, Read-Only.
Drive screen looks a bit different…
Through a mix of experimentation got connections working as needed. Solution came from a mix of port management through Synology and home router.
• Tidy up after all the experimentation
• Get automated backups configured
• Start the media server effort.
Everything has been running super smooth. So long as everything is connected to TS it is great. Exhausted the searching and tutorials for this next piece…
Heading out of town and decided to spin up plex for the time away. There is a media server on a Mac, and one on Synology. Both work great with apples like Jellyfin, including remote.
Plex is working as expected for the Mac, however not getting plex to connect to the Synology Plex Server.
Goal here is for Plex to connect when TS is on, the way everything else is connecting. Also open to connecting through account credentials as we do have plex pass, so long as it does not requiring going through opening ports on Synology or primary router (and vm the beauty of TS.)
Why won’t Plex connect to Synology server through TS? Any way to add a Plex connection using IP and credentials - to enter the TS IP, port and that way no need to sign in?
(Plex server on synology is successfully signed into the Plex account, however warning messages in the remote access setting.)
Presume someone here has would be successfully connecting to Plex on synology via TailScale.