Plex Media Server on Synology 920+ (Issues Playing Media) Please Help!

Thanks for clearing that up for me. I now understand this is a Linux directory listing. I am just not used to seeing the files in this format.

The file naming format you shared makes sense to me and is how I’ve tried to name most of my files. The folders are off, so I would need to move all the files into one sub-folders by season.

I will look into a step by step tutorial for Filebot. I think the investment is worth it. I am wondering if once I can use Filebot to reorganize and move my files, how do I ensure that newly downloaded or added files continue to be moved into a subfolder and not create a new folder automatically for each file/episode. Would that be a Filebot fix or a FileRenamer thing? Does that make sense?

Also, would I be downloading Filebot for Synology or for my mac?

Depending on the program you use, it should be able to rename (by also performing a lookup) to the official names and place them where you want.

I would recommend download for Mac. You’re familiar with the Mac.

You can drag & drop with ease there.

Mac directory structure is the same as Linux /dir/dir/subdir/file format
MacOS comes from Unix. Linux comes from Unix as well.

I recommend making copies of the media to play with

Also I recommend creating a play “sandbox” for all this
Have a “Inbox” and an “outbox”

copy the files into the inbox
write the renaming rules to rename and place in outbox