I can't upload a picture right now as I'd have to reduce the quality due to permissions, and I don't know how to do that on my phone.
The leather is 1/4 inch thick, but one of the needles I'm using has a "spoon shaped" flat section that's over 1/16. I suspect that's my mistake.
As far as sole bend tearing, on a test piece, if I pierce through, it pretty easily tears if I try. A little twist of the awl will do it. Is that abnormal?