Question Block Filled Cookies


Sugar cookies filled with surprise candy.

You can use any sort of small form candy for filling for these candies. I used tiny M&Ms, but you can mix it up. Tiny Reese’s Pieces, chopped up peanut butter cups, chopped up Oreos; the possibilities are endless. You do want to have a small candy form factor, otherwise the cookie won’t fit together properly.


Sugar cookie dough
Candy for filling (I used tiny M&Ms)
Yellow food coloring
Orange food coloring
Black food coloring marker
Flour for dusting


Big square cookie cutter
Smaller square cookie cutter
Sealable plastic bag

I’ve done Question Block Brownies before but haven’t tackled these in cookie format yet. So here we go!

First step is to take your sugar cookie dough and work in a few drops of the yellow food coloring into it until it’s fully incorporated.


Roll out the dough on a floured dusted surface until it’s about 1/4″ thick.

The essential piece of equipment are these square cookie cutters. You’ll need two of them, one larger and smaller. The smaller one was two sizes smaller than the larger one.


Once you have your dough rolled out, cut out three large squares.


Use the smaller cookie cutter on one of the larger squares.


Place the square outline and the two larger squares on a cookie sheet. If you have two cookie sheets, place the square outlines on one sheet and the full squares on another. The outlines will cook faster, so it’s better to have them on a different sheet, but it’s not a big deal if you only have one sheet.


Bake at 375F for 6-8 minutes, or until the edges are golden brown.

Allow the cookies to cool.

For the glue to hold the cookies together and to create the question mark, mix in a few drops of orange food coloring into white frosting.


Mix until the color is fully blended.

Scoop the frosting into a sealable plastic bag and snip off the tip.

Taking a cooled cookie, draw on a question mark.


Using theĀ edible food marker, add dots to all corners of the cookie.



Now to assemble the cookie! Take square cookie (the one you haven’t frosted) and flip it over.


On the flipped over cookie, draw on an outline of frosting.


Gently press on the square outline on top of the bottom cookie.


Now you can fill the cookie with whatever candy makes your skirt fly up. I used tiny M&Ms.


Add another layer of frosting along the rim.


Press on the top cookie.


Side view

Side view

Repeat for all cookies.


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