Display Order not changing Play Order?

[TheDreadPirate]

You will need to rename the files. Specifically the episode number. Because you named the file 1x01 it will be identified as the first episode in the order you selected, the episode name is pretty much ignored.

The file season and episode numbers in the file names must always match the metadata source and order you are using.

I also have the Cowboy Bebop bluray boxset and Asteroid Blues is named "s01e01.mkv" and Stray Dog Strut is "s01e02.mkv", etc. Jellyfin will always honor the season and episode number in the file name and match it up with the metadata from the episode order you selected. It will not assume "oh, you actually mean this", because it has no way of knowing what you actually mean.

When the orderings differ a lot between orderings, this can mean opening every video and skipping past the opening to the episode name since they aren't named when ripping them.

Due to some oddities with my Daria boxset, I had to open all 65 episodes and skip the opening to ensure the files were named right.

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There are some tools you can try. Tiny Media Manager MIGHT have a way to rename them automatically.