Metadata not following through or adding details to my content

Server Version#: 1.19.4.2935
Player Version#: Google Chrome

So very recently I noticed when adding to my Plex Media server it wasn’t loading the metadata, I made sure the files were named properly and used the Match button since that usually works. After adding a new batch of files to my server the problem persisted where it was pulling metadata really odd.
For example it was not loading the posters, but the name and dates happened to be pulled in. Or for TV shows it would recognize there was Metadata but would not automatically apply it, I would have to manually go in and put the poster on myself, but it was not naming episodes.

I guess what is happening is its pulling bits and pieces, but I have to go into each and every files and see what its missing where in the past it would just do all the heavy lifting. Has anyone had any problems with Metadata like this? This hasn’t happened to me in the past so I was wondering if there is some sort of fix. I also get an endless loop of refreshing metadata until I hit some weird button like Get Info or Edit

Eamples of the names and structures which fail? (exactly as you have one so I may test).

EDIT:

PS: Is this on a Windows server or a Synology server?

It is on a Synology Server

Okay the way much of my content is named for movies is this, Heres an example this was one of the files that failed to pull metadata (also the most recent addition when this started happening)
/volume1/Plex Server/Movies/Jurassic Park (1993)

For Television Shows
/Plex Server/Adult Cartoons/The Venture Bros. (Seasons 1-6 )
and of course the episodes all contain S01E3 etc etc

Its just not wanting to completely fulfill all the metadata and it gets stuck in a loop until it stops and nothing changes

please include the names of the files (copy/paste the text names).

I cannot test using only directory structure.

(Venture Bros Episode) S01E01 Dia de Los Dangerous! [480p] [h.265].mkv

(Movie) Jurassic.Park.1993.720p.mp4

Your format for “The Venture Brothers” is not correct.

Using:
https://thetvdb.com/search?query=the+venture+brothers

Correct naming:
The Venture Bros - S01E01 - Dia de Los Dangerous [ 480p] [h.265].mkv

You will notice only season 1 is listed.

Jurassic Park should be straight forward unless an MP4 or if you have naming similar to what you showed above with Venture Brothers.

Jurassic Park (1993)/Jurassic Park (1993).mkv

If you have a lot of issues like this, I recommend a renaming tool. It REALLY helps.
I use FileBot. Since starting to use it, I’ve not had a single matching problem.

FileBot takes the name we give it, performs a lookup, proposes new naming for us to select / confirm. When we do, it will create proper structure and rename as we’ve defined.

My FileBot rules are:

movies: /nas/movies/{n} ({y})/{n} ({y})
tv: /nas/tv/{n}/Season {s.pad(2)}/{n} - {s00e00} - {t}

n = name,
y = 4 digit year
s = season [ .pad(2)] - adds a leading zero if required ]
t = episode title

I did create a test series but found one already in my QA library.

[chuck@lizum tv.516]$ cd The\ Venture\ Bros/
[chuck@lizum The Venture Bros.517]$ ll
total 76
drwxr-xr-x   9 chuck chuck  4096 Sep 29  2016 ./
drwxr-xr-x 932 chuck chuck 45056 Jun 30 13:17 ../
drwxr-xr-x   2 chuck chuck  4096 Sep 29  2016 Season 00/
drwxr-xr-x   2 chuck chuck  4096 Sep 29  2016 Season 01/
drwxr-xr-x   2 chuck chuck  4096 Sep 29  2016 Season 02/
drwxr-xr-x   2 chuck chuck  4096 Sep 29  2016 Season 03/
drwxr-xr-x   2 chuck chuck  4096 Sep 29  2016 Season 04/
drwxr-xr-x   2 chuck chuck  4096 Sep 29  2016 Season 05/
drwxr-xr-x   2 chuck chuck  4096 Sep 29  2016 Season 06/
[chuck@lizum The Venture Bros.518]$ ll *01
total 60
drwxr-xr-x 2 chuck chuck 4096 Sep 29  2016 ./
drwxr-xr-x 9 chuck chuck 4096 Sep 29  2016 ../
-rw-r--r-- 1 chuck chuck   54 Apr 26  2016 The Venture Bros. - S01E01 - Dia de Los Dangerous!.mkv
-rw-r--r-- 1 chuck chuck   51 Apr 26  2016 The Venture Bros. - S01E02 - Careers in Science.mkv
-rw-r--r-- 1 chuck chuck   48 Apr 26  2016 The Venture Bros. - S01E03 - Home Insecurity.mkv
-rw-r--r-- 1 chuck chuck   58 Apr 26  2016 The Venture Bros. - S01E04 - The Incredible Mr. Brisby.mkv
-rw-r--r-- 1 chuck chuck   62 Apr 26  2016 The Venture Bros. - S01E05 - Eeney, Meeney, Miney...Magic!.mkv
-rw-r--r-- 1 chuck chuck   55 Apr 26  2016 The Venture Bros. - S01E06 - Ghosts of the Sargasso.mkv
-rw-r--r-- 1 chuck chuck   58 Apr 26  2016 The Venture Bros. - S01E07 - Ice Station - Impossible!.mkv
-rw-r--r-- 1 chuck chuck   51 Apr 26  2016 The Venture Bros. - S01E08 - Mid-Life Chrysalis.mkv
-rw-r--r-- 1 chuck chuck   67 Apr 26  2016 The Venture Bros. - S01E09 - Are You There, God! It's me, Dean..mkv
-rw-r--r-- 1 chuck chuck   54 Apr 26  2016 The Venture Bros. - S01E10 - Tag Sale - You're It!.mkv
-rw-r--r-- 1 chuck chuck   43 Apr 26  2016 The Venture Bros. - S01E11 - Past Tense.mkv
-rw-r--r-- 1 chuck chuck   57 Apr 26  2016 The Venture Bros. - S01E12 - The Trial of the Monarch.mkv
-rw-r--r-- 1 chuck chuck   62 Apr 26  2016 The Venture Bros. - S01E13 - Return to Spider-Skull Island.mkv
[chuck@lizum The Venture Bros.519]$

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