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There is an error in the Chess Live game. It won’t allow you to castle if EITHER rook has been moved. If only one rook has been moved you should still be able to castle with the other rook so long as you meet the other castling rules.
I found that too. In at least one other case, I found that an illegal move (failing to move out of check) resulted in the illegal move standing - and the checked player having another move. Odd, indeed.
For more information about that channel's features and functionality, you'll want to contact Chess Live support directly to inquire further. Many channels on Roku are developed and maintained by the channel provider themselves.