After having successfully used Watchtower to keep certain other Services up to date, I now use it to do the same for Plex.

For context: For some reason Plex auto-update never worked for me, which is why I always had to manually download the Synology Package and manually apply it.

And without the knowledge how hard it would be to provide updates via Synology Package Manager, that was fine. But after having seen that Plex got early access to DSM7 to get their software ready for it, and seeing how seemingly easy it was for the Tailscale and AirConnect guys to provide auto-updates, this can’t be the reason. Plex is just outright too lazy to do it.

They do seem to regularly update their Docker images though, which is where Watchtower now comes into Play.

Migrating Synology Plex to Docker Plex

I stopped the Synology Plex to free up the needed ports and followed the instructions to set up the Container, … aaand it didn’t work. The config folder and the Media Directories I mounted into the Container weren’t readable, I checked the Access Permissions in the Synology File Manager but everything looked fine there. Then I opened a Shell within the Container (which the Synology Docker UI thankfully makes a breeze) and explicitly set the permissions there:

# chown -R 1000:1000 /config
# chmod 755 /video /music /audiobooks

The Media directories permissions being broken I somewhat get, user-provided and all, but I can’t understand the config part.

Regardless, after that it ran smoothly and a “quick”¹ scan and re-import of my media files later, it all works fine. And now watchtower will tear down the container and rebuild a new one with the updated Image, whenever Plex publishes a new Image to Docker Hub.