Here’s the problem and it’s as thought.
Dec 19, 2019 09:57:36.786 [0x7efbedc63700] ERROR - Error creating directory "/volume1/video/Movies/Spider-Man - Far from Home (2019)/Plex Versions/Optimized for Mobile": Permission denied
You’re using the defined video share. Synology has historically caused problems there because they have special permissions beyond our control.
I recommend moving to a dedicated “Movies” share (also repeat for other library sections).
Here’s the HowTo on moving the data without losing metadata or watched status history.
Now, on Synology, Remember to give user Plex R/W permission to this new share as well as giving your username R/W permission.
