This isn't a problem I've had with any of the other calibers I've loaded (10mm, .44 Spl & Mag, .41 Mag, .45 Colt, .32 Auto, .45 Auto).
I've tried lubing the cases (even though I use Dillon or Redding carbide dies), and even a dash of case lube on the powder funnel itself without any improvement. It's worse with nickel cases but is noticable with yellow brass as well.
Strangely enough, I did run into this FAQ entry on Starline's web site.
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Why is it very hard to get expander and powder funnel back out of case?
There are two situations that create this problem. The first is one we have just recently identified. It seems to be associated with the dillon powder funnel and only a couple of calibers (45 Auto and 40 S&W). The land for expanding case mouth is too long and when you begin to bell mouth the bottom of expander gets into the thicker taper of case and wedges causing it to be very hard to get back out. We have modified several by increasing radius on end and slightly shortening expanding land and this eliminated the problem completely. Call Starline and we will take care of it if you wish. One other cause can be a burr at case mouth created by the final trim operation, which grabs onto expander as it comes back up. This situation does not often appear and can be fixed by deburring case mouth or inside lubing cases.
There are two situations that create this problem. The first is one we have just recently identified. It seems to be associated with the dillon powder funnel and only a couple of calibers (45 Auto and 40 S&W). The land for expanding case mouth is too long and when you begin to bell mouth the bottom of expander gets into the thicker taper of case and wedges causing it to be very hard to get back out. We have modified several by increasing radius on end and slightly shortening expanding land and this eliminated the problem completely. Call Starline and we will take care of it if you wish. One other cause can be a burr at case mouth created by the final trim operation, which grabs onto expander as it comes back up. This situation does not often appear and can be fixed by deburring case mouth or inside lubing cases.
Burrs aren't an issue for me. Has anyone else seen this? It's annoying enough -- clunky press operation, spilled powder, etc -- that I am tempted to take up Starline on their offer.

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