I don't remember when I first saw a gingerbread house with color candied windows but I do remember being amazed. I didn't know you could do that! That house used yellow candies, probably to simulate the glow of candlelight. When putting together my family's holiday gift assortment, I knew I wanted to use this candy window trick - but on what?
When I was a little kid, we'd make ornaments with our names on them using Elmer's Glue and glitter. Seriously, what kid doesn't love seeing their name on the tree? However, I wasn't handing out ornaments; I was baking. By combining the candy window and my childhood ornaments, I now knew what to make: Monogrammed Ornament Cookies. Now I just needed a few pounds of Jolly Rancher's.
As far as how many cookies you'll yield goes, I haven't finished baking all of the cookies yet so I don't know. However, since there's barely any cookie dough being used, any one recipe will go pretty far. The candy on the other hand, you'll probably need more than you think. Each cookie, which measures roughly 2-1/2 inches, uses roughly one candy.
You can use any hard candy but I prefer Jolly Rancher's. The candies are pretty transparent, don't have any chewy center, and they taste pretty good. I inadvertently purchased some hard raspberry filled candies because they were cheaper but when I hammered them into smaller pieces, there was some gooey filling that stuck to the hard candy. I picked most of it off but didn't think it would be an issue. I filled the cookies with the candy shards and when baked, the gooey filling bits burned, leaving black swirls in the otherwise pretty color. Lesson learned.
When hammering the candy, put them on a cutting board and not directly on your counter. This is definitely not scientific, but I feel like the cutting board helped absorb the impact of the hammering and the candy smashed that much faster. Also, leave the candy in its wrapper. The wrappers are much thicker than most plastic bags and will keep the candy from exploding sweet shards all over your kitchen floor. Another lesson learned. Also, if you don't manage to break them into small enough pieces before unwrapping, then put them in that plastic bag and hammer away.
Place a very chilled cookie ring on your parchment paper lined cookie sheet and sprinkle some crushed candy in the center, being careful not to get any on the dough. Place a chilled cookie letter on top and bake the cookies as per your recipe. The letter may shift during baking so when you take the cookies out of the oven, you may have to re-center it. Use a toothpick to move it. Work quickly if there are many that have shifted because the candy will start hardening. Let cool on the sheet pan. Peel off, hold them up to the light and revel in your holiday craftiness.
As I mentioned in my comments, as I continued to bake, the process and results improved. So to have the best-looking cookies possible... Bake just the cookie dough portion 70% of the way through (both the rings and initials), leaving about 3 minutes of bake time. Don't put the initial in the center of the ring yet. Remove the cookie from the oven (shut the oven door) and fill each ring with some crushed candy. Put the tray back in the oven for the remaining three minutes. Check to see how melted your candy is - you may need to bake them for more or less time, depending on how finely crushed the candy was to begin with. Once melted, remove the tray from the oven and quickly place and gently press the cookie initial in the center of each melted candy. Done!