Transposing the Chord Track

Except the cords only sometimes change accordingly, other times they won’t change at all or they will only change to some roots and not others. This has been reported by numerous folks on several different threads. We’re trying to understand what differentiates one situation from the other. Are you saying that if you create a B followed by a C chord (in that order) that you can select both of those chords and successfully transpose them via the Root Key? I know they won’t on both my PC and Steve’s Mac.