Chocolate Cinnamon Chipotle Sugar Cookies

Our baking assignment this Sunday were the gorgeous chocolate cinnamon chipotle sugar cookies in celebration of the Day of the Dead. While I question some of the dessert-themed holidays in Baked Occasions, Día de Los Muertos is the kind of holiday more people ought to recognize. Remembering our loved ones is a beautiful tradition and these cookies would have been a hit with both my grandma and Nana (hold the spice).

As enthusiastic as I was about baking for the occasion, I wasn't particularly excited about these cookies specifically. I don't like crunchy cookies and in my experience, all cookies as intricately decorated as these chocolate cinnamon chipotle sugar cookies don't actually taste good. Honestly, all beautiful decorated desserts tend to not taste that good, in my humble opinion. Plus, the artistic genes missed me by several miles. I won top honors in my Photoshop class in high school (and I still don't understand why) - that's as close to artistry as I'll ever get. All this is to say I normally skip fancy decorating even if it's called for by a recipe (see the chocolate malted brownies as a recent example). Decorations don't really add flavor, just more work for me, and pretty things are less likely to get eaten because people feel guilty about ruining them. But this time, this time I told myself I'd follow directions and do my best to honor the occasion with my decorations.

Making the cookies themselves was far and away the simplest step. As recommended, I made this recipe of the course of two days. First I melted chopped Scharfenberger 99% unsweetened dark chocolate by microwaving it in 30 second bursts for a total of 1 minute 30 seconds, stirring after each burst. The recipe called for dark chocolate and I'm assuming that implied 70% rather than 99%, but I love how mine came out, they are exactly the right amount of sweet as they are.

Once the chocolate cools, simply mix the butter and shortening, cream them together with the sugar for about 4 minutes, add the egg and vanilla, then the cooled chocolate, and finally the whisked dry ingredients. (The recipe called for chipotle or ancho chile powder as the spice, but I didn't have either, so I used pasilla chile powder instead.) Although Matt & Renato instruct the baker to pat the dough into a round and refrigerate it before rolling, I patted my dough out between two pieces of parchment paper to ½-to-¾-inch thick before chilling it. I find it a lot easier to roll out cookie dough while it's still soft instead of struggling with too-firm dough that then warms up too much while I'm trying to roll it to the right thickness. No one has ever explained why rolling it out first is a problem, and I haven't experienced any issue with my routine, so I'll keep on doing it.

The shortening in this dough ought to contribute to a malleable dough, but I was happy I had prepared my dough slab before chilling because when I attempted to roll it out to the specified ¼-inch thickness after chilling, jagged cracks appeared throughout the entire dough block, splintering the edges and even the middle. I opted to cut my cookies from ⅓-to-½-inch thick dough instead of trying to get it any thinner. You may have noticed that my cookies aren't exactly skull-shaped, right? I did look for a skull-shaped cookie cutter, but I didn't go hunting until after November 1st and nowhere I looked carried them, so I used my 3-inch diameter round biscuit cutter instead. It seemed more fitting than a star or reindeer head, which were my other options. With this shape, I wound up with 16 round cookies instead of 12 skull cookies.

After freezing my shaped cookies for 15 minutes, I put them all in the oven together, ignoring the guidance to have 1 inch of space in-between (for proper air circulation). Since I worried about having crunchy cookies, I cooked these for the absolute minimum amount of time. A few of the thickest cookies did still look a little wet on top, but I like slightly underdone cookies so I was fine with that. I'd always rather eat a slightly underdone cookie than an overdone cookie. Especially if I've put time into decorating it.

Once my cookies cooled, I made the royal icing for the base layer. (It should be noted that this icing includes raw egg whites. Buy your eggs from a trusted source and use fresh, clean eggs.) With just the initial amount of powdered sugar, my finished icing seemed too runny. I added another ¼ cup more and beat the icing until it was really white and smooth. Now we were approaching the problematic phase for me. I don't actually own any pastry bags, so after some deliberation I decided I could use the icing tip on my cookie press to shape both the icing wall and to fill it in. This was surprisingly simple, although the tip was small enough that it took a while to fill in the whole circle without leaving any gaps. After this step I still had a lot of icing leftover. At least a cup or two. I decided to refrigerate it and use it for my decorative icing in the morning because I hated to throw it away.

After an overnight rest, it was time to take on the decoration phase. Clocking in at over three hours, this step took me three times longer than the other two stages combined. The first stumbling block came when I realized I'd used up almost all my black food gel coloring for the conversation hearts last year. Next came my decision to use the cookie press icing tip to form the decorations. As great as this tool worked for putting down the base layer, it wasn't nearly fine enough to use for intricate patterns. Add in my shaky hands when tasked with minute movements and my cookies were in trouble. A few cookies in, I was pretty unhappy with how the decorating was going and considered filling in what I'd done and just serving the cookies as color-blocked rounds.  Instead, I stuck with it and finished the black decorations with the cookie press, switching to snack-sized Ziploc bags with the teeniest corner sniped off for the colored icing. This worked a lot better, but as time went on, the opening enlarged and I lost fine control over the icing. In addition, I struggled with dried pieces of icing chipping off the top of the bag where I'd added the icing and falling in flakes all over my cookies.

These chocolate cinnamon chipotle sugar cookies are delicately spiced with a mellow chocolate flavor. The royal icing isn't too sweet, which was a pleasant surprise. The individual spices come through faintly, this isn't an overly spiced cookie with just a little cinnamon and a mild heat from the chile pepper. The cookies themselves remind me of the Mexican hot chocolate shortbread cookies I adore from the Back in the Day Bakery cookbook, only these are less chocolate-y. In my opinion, the ½-inch thick cookies cooked only 10 minutes were perfectly done for me, although I know these are supposed to be a crunchy cookie and I did everything I could to prevent that outcome. I would certainly make them again, but would I bother with decorating them again? I love how bright and colorful they are - I think it could be a lot of fun to decorate them with other people. Like a pumpkin-carving party, but better because you get to eat the result.

Head over to Baked Sunday Mornings for the recipe and to see what others thought of these.