External Subtitles only found when broken into child folders

[bjsummerfield_live_com]

When I make external subtitles for tv shows Plex cannot find them if I put them all in the same folder. If I create additional folders Plex will find and apply the subtitles correctly. I’d rather not create a new folder for each episode so what is going on here?? Please see attached

Here is when Plex will find the external subtitles;

And when I group multiple files in the same parent Plex is no longer able to find them correctly

I’d really appreciate some help on this topic

[BigWheel]

after refreshing metadata I would examine the local media log to see if there are any errors. There is a “Plug-in logs” folder in the logs folder. ( or download the zip with everything from the troubleshooting section of server settings)

[bjsummerfield_live_com]

Thanks for the link, I’ll correct the media file organization soon. Would this effect the issue I’m experiencing with external subtitles?

[bjsummerfield_live_com]

I’ll check the logs after re-organizing my media per trumpy81’s suggestion

[bjsummerfield_live_com]

Ok I moved my Plex files to a media folder per @trumpy81

@BigWheel, the issue has not gone away - here is a sample of the logs. I moved episode one and the subtitles into their own folder named ‘01’

As you can see it cannot find the subtitles for any episode except the one I moved into its own folder. Here are the folders on the NaS.

And a look inside the ‘01’ folder

I’m at a total loss so any help is greatly appreciated