OP take a look at the app Filebot. Will save you a ton of future headaches and correctly name your movie and TV shows.
While naming could generate problems, Plex itself has problems, even if the moderators try always to blame the user. I assume my names are OK because they come from Radarr/Sonarr. Still during the Agent upgrade Plex unmatched an unpleasant amount of movies that were already matched and they stayed unmatched. Of course the moderators are in this thread telling us thatās not possible. Well, what can I say?
What I expect from Plex and any other service like it is to honor the CORRECT naming. By this I mean for movies and TV shows I ALWAYS check TMDB and TVDB and use that as my guide for naming. The only time I check with other sources is if the two services have even the slightest difference in names for the item. I dropped Plex a good while back because of being told I had to name items different than what the official title is to get Plex to match them correctly. Was flat out told it had to be an enduser problem when I knew better. The difference between the Plex forums and the Emby forums is night and day. As far back as I can remember either the Plex forum staff chose not to help at all or in most cases put the blame on the enduser. That is beyond wrong.
Tried emby for a weekā¦YUCK is my experience coming from Plex. Deleted it and will not be going back.
Iāve used Plex for over a decade and I feel pretty confident in saying Plex DOES honor the correct naming of Movies and TV shows. Are you sure YOU are using the correct naming for your media? I know users hate to be told they are the issue, but sometimes itās the truth 
I canāt stress enough how useful Filebot is for Plex. You may THINK you are using the correct naming structures for your movies and TV shows until you try Filebot and do a match with TMDB.
Nearly every movie or TV show Iāve matched in the last few years has matched without issue because I stopped putting things that donāt belong in the file name.
Half the comments in here are ignoring the fact that Iām not importing a library fresh⦠this was an existing collection that has been fine for years with no matching issues. I am ignoring comments about user error, it simply is not the case. I too am a 10 year or so veteran user.
With that said, I have decided to nuke the entire movie DB, I was wasting too much time troubleshooting it and of course I saw your request for logs after I had already done this. Considering the fact that I was seeing a pattern of multiple mismatches in a row (and then it performing fine for a bunch) and refreshing wasnāt working to fix them in bulk, I decided to just kill the whole thing. Rematching all affected entries was just taking far too long to bother with. The last straw was a bug that wouldnāt let me change Agents - the one that says āYour changes could not be savedā no matter what you do. I read that this could mean that the DB had somehow been corrupted so I said screw it and wiped it. To make sure this was fool proof, I used TMM to replace all [ ]'s with { }'s even though this has never been an issue before (those were for other platforms, title + year should be more than enough to match). It has reimported fresh without any mismatches that I have discovered so at least thereās that.
You are correct though, thereās no reason why swapping Agents and then refreshing metadata would lead to all the mismatches, they were already matched so it doesnāt make sense why they would suddenly unmatch? As mentioned, Iāve used Plex for 10 years (2013 I finally bought my Pass) and dabbled with other platforms from time to time in that exact format without issue. All movies are contained within their own individual folder, along with their relevant images/nfos, and nested under the titleās first character parent folder. I do this for things like TMM so I donāt have scan the entire collection when I want to force an update for a specific title.
Barring periodic backups for the DB, Plex really should respect local nfo files in the event a rebuild is necessary. It would have saved me so much time.
Weāve made it VERY clear itās not us, deal with it.
From the one example above given of a movie file name it was very clear that was NOT the correct way to name in Plex. It would likely still match but could cause problems.
But yeah letās just blame Plex and never look in the mirror. Smart choiceā¦
I myself upgraded matching and had 0 movies unmatched in a medium-large size library. Iām on MacOS so not sure if itās something OS dependent or not.
Iāll bow out of this convo as I havenāt experienced this issue. However Iāll say again to everyone who has issues with matchingā¦Filebot is your friend 
Square brackets were the culprit to my incorrect matches so there is definitely a reason to avoid using tags inside square brackets.
Running a few test files isnāt nearly enough to verify anything - you need to do thousands of different files with proper naming + tags instead of random characters + tags.
Maybe your files are matching due to Plex not finding anything named abcdefg so it then searches within square brackets as there is no other name info to use? Who knows.
I havenāt noticed any issues since changing to { }so thatās a clear winner.
I agree, name 'em correctly, as per the documentation!
If nothing else, you get to be really righteous about it when thereās a problem and you ask for help. LOL 
I dunno why I felt it necessary to comment. I didnāt add anything to the discussion by saying āsquare brackets kinda workā, when I do strongly advocate for following the docs.
When I was testing, I found that putting an ID in square brackets or squiggly braces would override almost anything else. But that was a handful of test files, not a library of ādifficultā things. Iād be interesting in knowing some of the filenames that didnāt behave that way for you.
Somebody - maybe MovieFan.Plex, or maybe drzoidberg33, or maybe OttoKerner - once stated that only the first set of brackets in a filename are ignored. I think that points out how complicated the filename parsing process is.
Thanks for the update. Iām sorry to have distracted!
RIGHT!, except you also have a PLEX NINJA telling you to get rid of the square brackets which would be what? ⦠a naming issue. Sorry not sorry.
Just because one agent didnāt mind it doesnāt mean the new agent doesnāt.
Apparently the new agent doesnāt like square brackets ⦠yea, weird huh.
What do you mean with ātagsā?
Plex doesnāt reads tags from file names at all.
If you need to put info into the file names which are not covered by the naming guides, you need to hide them from Plex. So they donāt throw off the scanner and lead to mismatches.
That is what the square brackets are for.
Tags as in IMDB/TVDB IDs. 
ahh IDs ā not tags.
It is clearly documented how to indicate these properly: Naming and organizing your Movie files | Plex Support
Naming and Organizing Your TV Show Files | Plex Support
Might be of interest for some, regarding storage of metadata⦠mp4 files can be used to store metadata settings, even if you use an .mkv for the movie.
A .mp4 file can be used for the movie, or an empty .mp4 (no streams, just metadata) can be saved alongside the move (similarly named). The old Plex scanners have read the poster artwork, and certain tags from the .mp4 metadata, to populate various details in the home page for the movie, when the movie is added to the library. This could be very useful if the library needed to be rebuilt from just the files.
mp4 metadata I found to be read by Plex are:
Poster artwork: {equivalent to the poster.ext file}
Name: {Must match the TMDb title}
Genre: {Up to two comma separated text fields}
Release Date: YYYY-MM-DD {Year must match TMDb title. Use that, in preference to the TMDb release year, if they donāt match.}
Long Description: {Can be fairly long and verbose. Length limit unknown. One long line. Separate paragraphs merge into one}
Studio or Copyright: {If Studio info exists, it will be displayed, otherwise the the Copyright info will display in the āStudioā line of the movie homepage.}
Director: {comma separated list of Director names}
Screenwriters: {comma separated list of Writer names}
Cast: {DO NOT USE! a comma separated list of actor names, but using this field breaks the photo image for the actor, even if you remove the Cast: tag from the MP4. (I tack on a list of actors in the Long Description)}
Tools for editing metadata of .mp4 files:
macOS subler.org - Subler
Windows danhinsley.com - MetaX
I use Subler and canāt vouch for how well MetaX works with Plex.
Itās a lot of work putting your meta data in an MP4 file, but it will pay off the first time your Plex database becomes corrupted and you have to rebuild from scratch. I wish there were similar side loaded files were we could define things like Collections and Playlists.
I donāt know how the new scanners will deal with MP4 metadata, but I hope it continues to work. I monitor this topic with keen interest and am holding off refreshing all my metadata, hoping that the problems iron themselves out.
Sorry, but Plex does not respect metadata in the file even when that option is checked. Itās not rocket science logic to look at metadata in the file for season number and episode number. Relying on file naming as a first and/or last resort when there is metadata in a supported container format is just plain bad design.
It would be one thing to mismatch a series name. But if the series name is matched correctly but the season and episode numbers are ignored then I just am a loss for words. Yet, thatās what I often experience.
Hereās the logic I recommend:
- Match on series. Let me override this in the UI. Then store that in the database.
- Next, match on the season. Let me override this in the UI. Then store that in the database.
- Next, match on episode. Let me override this in the UI. Then store that in the database.
My workflow is simple. I convert to m4v container with appropriate supported codecs. I add metadata with Subler from thetvdb.com or tmdb.com. I add the files to iTunes / Apple TV library. I point Plex at the folders for that library - separating Movies and TV libraries. Then Plex manages to - sometimes - completely ignore the metadata.
Why?
Google dropped me off here⦠tried to read through all this before posting.
I too just converted to the ānewer fasterā Plex agent at the request of a pop-up on Mac. It ran through my entire 1000+ film collection, no problem. Not one issue cropped up. BUT, and itās a BIG BUT, now I canāt add any new movies. It straight up refuses to match any movies I add. I donāt know what changed (not a cool code monkey), but nothing is matching when I add a new film.
And Iām not adding indie unground goth fetish movies⦠āFantastic Four (2005)ā is about as mainstream (with correct naming convention) as it gets. I even tried various other variations using { } and brackets. Even went so far as to try out Filebot. Nothing. No matching love.
Assuming itās not user error (that was my first card played), what else could it be? For science!
The main problem with the new agent is the only agent available. It is fast but not complete. Lots of popular shows are not in the DB. It merge a lot of TV shows that not listed in the DB to other TV shows. Unfortunately Plex do not handle TV duplicates well. In general marking duplicates is non existence since few updates back.
Double check youāre TV shows and movies to make sure it not merged with other TV shows and movies. The new system is a pain.
Well, thatās weird; it started matching again this morning. Didnāt do anything more than let it sleep over night. Must be a gremlin in the system or it was doing something in the background. Either way, back to normal.
There was an issue that we picked up this morning where some newer shows were not getting picked up (this was a recent regression). This should be resolved in the next day or two.
Could you give me an example of some of the shows that arenāt matching for you?
tested it for 1 month butā¦
it doesnt work at all⦠90% of my content ( 358 series ) is matching to āZero One-Once in Adanaāā¦
many series are combined and twisted ( sometimes it adds one episode from another series that is in a complete different directory ).
all names are identical to the tvdb entry names ( worked for over 4 years almost perfectly ) so there is no problem on my side.
another problem that came with the new agent ( and the new synology major version update ), sometimes files and directories are ignored - you need delete the file and copy it again a few times until plex register it and you see it in the notification log
examples for series that doesnt match: The Vampire dies in no time, Mieruko-chan, The Worlds Finest Assassin, Banished from the Heros Party.
edit: here is my full path to series ( no special stuff, just the tvdb name ): ā[ā¦]\Storage\Animes\Mieruko-chanā