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I just had this issue.. You have to remove a player from the 28 man roster, either demote, waive or release, then you'll be at 27 and can then move over an eligible player to the playoff roster. You'll see you'll be back up to 28 players on your active roster. You can do this more than once as long as you free up a player on the active roster and pull from your available playoff roster. (max of 26 players on playoff roster if you're using MLB rules)
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