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Tint 1/2 cookie dough red, 1/4 rose, 1/4 copper (light skintone). Roll out red dough and cut floor and ceiling cookies using pattern.
Use lollipop stick to make holes in floor cookie for bars and prisoner.
Cut one of each size heart cookie from rose dough; cut smallest heart from red dough.
Roll out copper dough and cut prisoner using largest teddy bear cutter; cut ears off cookie. Bake and cool all cookies.
After baking, make sure the holes are still open in jail floor cookie. If holes close, use lollipop stick to reopen while cookie is still warm.
Using royal icing, pipe tip 4 hat and uniform stripes. Trim 14 lollipop sticks to 9 1/2 in. long.
Cut another lollipop stick in half and attach to back of prisoner for easel with melted candy.
Using royal icing, pipe tip 2 string mouth, eyebrows and hair. Pipe tip 4 dot eyes and pupils.
Wrap craft block with foil and attach floor cookie to base with melted candy.
Insert lollipop stick bars and prisoner cookie through holes in cookie and into craft block.
Attach ceiling cookie to bars with melted candy. Using royal icing, print tip 2 message and keyhole on smallest cookie.
Attach heart cookies to bars with melted candy.