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Default cookie shapes won't come up with cookie cutter

I'm trying to make some cut-out cookies using storebought cookie
dough, using the instructions on the container, but whenever I roll
the dough out on a floured surface, flatted it, and press the cookie
cutter down to make the cookie shapes, the cut-out shape won't lift up
with the cookie cutter, making it too soggy and flexible to transport
to the cookie sheet. Strangely, the first two cookies seem to come up
properly, but any ones after that are impossible to get. Is it
because the dough becomes too moist after being handled for a bit? Is
the solution then to just keep mixing in more flour, not just enough
flour to keep it from sticking to the surface where I'm rolling them
out? Or what else?

 
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