Not the problem. The bolt was clean inside and the tool was fully inserted and seated in the fastener. I was also careful not to let the tool wobble over as I was trying to loosen it. The Craftsman bit socket was just too loose a fit. That much I am sure of.
How well do SK bit sockets fit compared to Snap-On? The reason I'm asking this question is because I was working on my Suzuki Intruder recently and stripped out the inside of one of the allen head (internal hex head) style bolts with a Craftsman bit socket I was using. The bolt was very tight...