I do have it set to "Ask" in Options but I don't understand why it's even asking.
I'm not following you...why wouldn't clip length be the issue? If I have Clip 1 of 20 seconds and Clip 2 of 20 seconds and a crossfade transition of 1 second, the transition should split the difference between the two clips, correct? It should use the last .5 sec of Clip 1 and the beginning .5 sec of Clip 2.
My clips have enough yet I get the warning message.