> For whatever bizarre reason, Plex all but requires you conform to specific filename formats. I don't why, but this pisses me off to no end.

Idk, on Kodi I had to rename my files a certain way for them to be associated with metadata from IMDB & all, so I was used to having Filebot[1] doing the job for me. When I switched to Plex, I didn't even think about it, I kept renaming my files with Filebot. Also I prefer the light and clearer pattern that is resulting from Filebot instead of having weird filenames depending on the release.

[1] : https://www.filebot.net/

Yeah, I got filebot now too. I wish it didn't have to exist, but Plex practically demands it!

The reason for the file naming convention is for metadata matching. All they are really doing behind the scenes is searching the movie name (and possibly year) from a metadata provider. The files you obtain online or rip yourself themselves rarely have any metadata in the file so the only remaining option is to parse the filename/directory structure.

Right, that's understandable, but many folks prefer to not rename files.

I would like to be able to just point to a file and tell Plex what that file is so it "knows" (puts it in it's database). If it can read/write metadata on the file itself, that would be great too.

> but many folks prefer to not rename files.

That's like arguing that they prefer an unsorted pile of thousands of books vs. a library/bookstore. I mean if that's how they want it then fine, but you don't get the useful features.

There are a multitude of metadata managers out there which don't require the same directory structure but they are a load more effort than automatic metadata matching and a lot more effort than simply organizing your media in the first place.

The answer is simple: not every media file is an MKV that has metadata inside it.

Your solution works for MKV files. The Plex solution works for all file types and containers.

It's easy to see why Plex would prefer this way.

Yeah but Plex, I believe, also maintains it's own database for the media files. Why can't I just "tell it" the metadata in those cases and leave the filenames as is?

Why don't you?

It has an edit button in the UI for entering in the metadata to its database manually.

It has the option to prefer metadata already stored locally inside the container when populating its database.

It has the "match" button for interactively discovering and retrieving the metadata from an agent like IMDb or tvdb regardless of filename.

By default it tries to spare you having to do any of these things, but they put a lot of work into facilitating several alternatives when you'd rather do the work yourself.

In my own use case, I rip blurays, and these don't have the metadata populated. Files won't even appear in the UI if the filename isn't right, or it guesses completely wrongly based on just the filename. There is tucked away, really deep, some options for "unmatched" files. I had moved on to using filebot before trying that.

Still your question should be "why didn't I?" which only you can answer, not "why can't I?" You could.