Specials inline with seasons

Sorry this is just hard for me to grasp.

Does Plex really not have the ability of showing specials inline with the season they air in?

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Nope, but while playing, those specials should play at the right point if they have the correct airing date info.

Do you mean If I play a season it will include specials as it moves between episodes? Assuming the special aired in between those episodes?

Yes, that is the way it should work. Here is an example for Dr. Who. I played Season 1, and you can see the specials thrown in at the end before Season 2 starts. It should work the same with specials during the season as long as the aired date is correct.

is this the case for on deck?

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