Don-
The 1909 is an excellent action. I have one in 35 whelen, and it works great. If you can pick the empties out with your finger, then my guess is the claw extractor is not getting a proper grip in the case rims. Being controled round feed, its picking up the loaded cases and chambering them properly. Upon firing, the extractor seems to be loosing its grip on the case. I'm not sure why the extractor would be a little oversize, but it sounds like it. I would spend the $ to have a gunsmith properly fit a new claw extractor. Shouldn't be that much.
Larry