Plex in Synology is not able to find Metadata until a Stop / Restart is undertaken

If you don’t follow the documentation, then Plex may work, until it doesn’t.

Start by adding correctly named season folders for the show. That takes maybe two minutes.

Per the docs, . is a valid separator, so you don’t have to replace them with spaces.

Plex should ignore everything after sXXeYY (ex: it ignores episode names), so you may not have to remove the extra info.

Performing the Plex Dance, if needed, takes a few minutes.

You can also try resetting permissions. Synology will sometimes mess them up. See FAQ 29 - DSM 7 - Give PlexMediaServer access to your media. Follow the process even if they look OK in DSM.