How To Add Specials That Should Be In The Middle Of The Season

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So I have a big problem.
I have a number of shows that have specials or OVAs or Movies that take place in between episodes. Now, I know for the TVDB to identify them I need to put them in the Season 0 folder S00E01, but I don’t care about it automatically identifying them, I’m happy to manually do the work to get my stuff to sort as I like it. For most the OVAs come at the end of the season & I simply name them the number after the last episode S01E13 or S03E13, but some shows have the problem of having a continuing numbering system. So Season 1 ends at episode 24 & Season 2 starts at episode 25. This makes it problematic, but still doable, we just have a Season01E25 at the end of season 1 & a Season02E25 at the beginning of Season 2. Not ideal but I can live with that.

Now here’s the problem. I have some shows that have a special that takes place mid season, Like it comes between S02E22 & S02E23. Now, in iTunes I can just name the Episode S02E22.5 & it will place it between the 2, But Plex doesn’t allow that. That naming makes it treat it like 2 versions of the same episode. Now, if it was just for me I would be annoyed at the inability & put in the Title of the next Episode to Watch S00E03 before starting. Annoying, but doable. But I have other people who are watching off of my Plex Server. I want the Episodes to automatically play next where they go chronologically, then continue to the next episode. But I have not figured out how to make this work. My options are Re-Number the episodes & make the special S02E23 then rename S02E23 to S02E34, & so on, & so on, Which is a HUGE hassle, because it makes all the rest of the episodes have the wrong metadata that I’d have to manually fix. I hate this option, but if it’s my only choice I’m willing to do it. Or have all the specials in a Zero Season which is an unacceptable solution I cannot accept.

Does anyone know of a less destructive method to accomplish this should-be-simple need?

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