It sounds like the resizing die isn't set far enough down. But there's more to it than that...
If those cases were shot out of the same rifle, you would think they would fit the chamber even if they weren't resized. That is the principal behind 'fire-forming' cases. In fact, many bolt-action rifle reloaders only resize the neck and never try to move the shoulder.
Check to see if a fired case, without resizing, will fit in the chamber. It should...
Another experiment: measure the height to the shoulder of a factory round. Fire it and see if the shoulder moves higher. If so, perhaps the chamber is a little long or the cartridge is assuming a smaller chamber.
You can get the SAAMI specs here:
The 32 Winchester Special is on page 74 of the document (page marked 68).