HELP! 

I have had no issues with simple cutouts, but when a cutter is like a butterfly, for instance, the little tail breaks off at times. Or If its an apple, the stem may break off.

I do chill the rolled out dough (between parchment) before I cut out and take great care to slightly assist the thin areas as I lift the cutout.

What I notice is that the dough may have some layers at times even though I have rolled it.

Please help and thank you!

Original Post

First, I use parchment paper and plastic wrap on top.  Second, try wiggling the cookie cutter before you remove the cutter.  The more times you use the cutter the better it will work.  May i suggest using a combination of flour and powdered sugar to roll your cookies.  They will dry out less and you will feel comfortable using more of the combo when you are flouring your cutter. God luck!

I'd suggest either freezing/refrigerating the cut cookies before you move them off your rolling surface (assuming you are rolling on either parchment paper or a silicone mat). Or (what I do) just rolling and cutting them directly on a silicone mat and then moving the entire mat (with the cookies still on them) onto the baking sheet. That way, you never have to move the cookies 'til they're baked and more sturdy.

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