I use a folder structure for my audiobook library.
All books are in single mp3 files.
When I access the books on any client (I use Fire TV mostly) including the web interface I go into the library using the folder view.
I will use one example to show the problem.
Folder is called Asimov
Under that folder are several files the a few are:
Foundation
Foundation an Empire
Second Foundation
If I have automatically play next track enabled and I play Foundation and it completes I would expect that Foundation and Empire would play next but that is not what happens. Rather “Chanur Saga - V01 - Pride Of Chanur” plays. That is from a completely different directory.
I noticed that in the web interface if I go into the library and use the folder view and go into the Asimov folder and click on Foundation I see the entire “Chanur Saga” along with a lot more listed as tracks of Foundation in spite of them not being in any way associated with Foundation in my folder structure. There are no subfolders of Asimov.
I believe that if “folder” is selected for viewing the library and a file is played from inside a folder then “next” should be the next file in the order in the folder NOT some other file from some completely different folder.
Is this a bug or is this simply the way Plex designed the system?
Well I found a solution or more properly a workaround.
I created playlists and manually added the books and, if they are not in the correct order, I can use the editing function to move them around.
It is not an ideal solution but it works. It just takes time to do it for my rather large Audiobook library.
Thanks to the Plex people for all their help. 
I get it. The problem is that the “folder” view is not a true file explorer but just a filter of the database. Internally, all audio files are stored as artist/album/track. So when the next track is requested, it will play the next track in that artist/album combo. There isn’t a way to get the next file in a folder. This is true for movies and tv shows too. There is a next movie (based on sort title) or next episode, but no next file.
Since Plex doesn’t have a way to store tracks not associated with an album, you need to either make a fake album to hold all those files, or place each track in their own folder making them singles.
Asimov
- Audio Books
— 01 - Foundation.mp3
— 02 - Foundation and Empire.mp3
— etc.
or
Asimov
- Foundation
— Foundation.mp3
- Foundation and Empire
— Foundation and Empire.mp3
etc.
@“MovieFan.Plex” said:
I get it. The problem is that the “folder” view is not a true file explorer but just a filter of the database. Internally, all audio files are stored as artist/album/track. So when the next track is requested, it will play the next track in that artist/album combo. There isn’t a way to get the next file in a folder. This is true for movies and tv shows too. There is a next movie (based on sort title) or next episode, but no next file.
Since Plex doesn’t have a way to store tracks not associated with an album, you need to either make a fake album to hold all those files, or place each track in their own folder making them singles.
Asimov
- Audio Books
— 01 - Foundation.mp3
— 02 - Foundation and Empire.mp3
— etc.
or
Asimov
- Foundation
— Foundation.mp3
- Foundation and Empire
— Foundation and Empire.mp3
etc.
Since I found that playlists will do what I want and I have already created most of the playlists I need for my library I am not going to bother with changing my structure. But thanks, I finally received an official answer and that is pleasant and unexpected.