Cookie Tour Recap – Mint-Filled Chocolate Fudge Cookies!

A note of warning… this blog posting is REALLY LONG because it goes into lots of detail about developing the recipe for the Mint-Filled Chocolate Fudge Cookies.  If you are just looking for the recipe and don’t want to be bothered with the details, feel free to download it here:  Mint-Filled Chocolate Fudge Cookie Recipe.  Enjoy!  If you are interested in the details, please read on and enjoy!
A few years ago, my sister-in-law got me a subscription to Cook’s Illustrated magazine and I was hooked.  I love how they go into such detail on each step of their recipes… telling you what worked AND what didn’t.  For some people, I’m sure they just skip to the actual recipe, but for me, I look at every step to try to understand what is going on and why.  Yeah, I know… I’m a geek.   I guess when you take the chemist out of the lab… she just moves into the kitchen!  I’m also a big fan of all things King Arthur Flour… their products, their store in Norwich, VT, their baking classes, and especially their recipe bloggers!  The King Arthur bloggers also do an awesome job explaining their recipes, usually with cute stories and TONS of photos.   So with Cook’s Illustrated and the King Arthur Flour bloggers and my inspiration, here is my attempt at recipe development.
Why this?  Why now?  It all started this past fall when Rob and I were starting to talk about our participation in the December Currier and Ives Cookie Tour.  (For more details on the tour, please see our blog posting from November 30, 2010.)  For some reason, I decided I wanted to do a mint-filled cookie.  Why mint?  I really don’t know.  I like mint, in moderation, but it really isn’t my favorite flavor.  Yet for some unknown reason, this was what I wanted to do.  The part that I do know is that from the very beginning I wanted the cookie to have both mint and chocolate… and the mint had to be inside the cookie, like a filling, not a mint-flavored cookie or something with mint chips.  (If you’ve ever put a mint-flavored or frosted cookie on a plate of other cookies, the mint flavor “travels” and everything ends up tasting like mint, whether you want it to or not.  My thinking was that if the mint was present as a filling inside the cookie, then it wouldn’t contaminate everything else on the plate.)
My first attempt, barely worth mentioning, was to make a Spritz cookie with an Andes chocolate mint candy as the filling.  While the concept might have been OK, I discovered that I just didn’t have the patience to work with the Spritz dough or the cookie press, and there just wasn’t enough chocolate in the cookies.
So with that idea out of the way, I moved on to the next one… a mint-filled chocolate cookie, reminiscent of a peppermint patty, but better.  Since I had recently been browsing the recipes on the King Arthur Flour website (did I mention their bloggers are great!), I decided to start my trials with the cookie dough for Magic in the Middles (a peanut butter-filled chocolate cookie).  The biggest problem was that the original recipe called for peanut butter added to the chocolate cookie dough.  Peanut butter and chocolate – good.  Peanut butter, chocolate, and mint – not-so-good!  So I had to come up with something to stand in for the peanut butter in the dough.  The challenge with this is that the peanut butter is not really a dry or a wet ingredient; it adds moisture, but it isn’t a liquid.  My “light bulb” moment happened when I was reading through some of the tips with the King Arthur recipe.  The suggestion was that if the dough was to be made ahead of time, then 2 tablespoons of milk could be added to keep the chocolate dough more moist and easier to work with.  Hmmm… milk… dairy… (light bulb) why not cream cheese!  So with that idea, I moved on to the chocolate dough recipe with a few additional changes.  I used Dutch-processed cocoa instead of regular unsweetened cocoa (more about this in a little bit), I added ½ teaspoon instant espresso powder (to intensify the chocolate flavor and help balance the anticipated sweetness of the mint filling) and I added ¼ cup extra flour (to give the dough a little more body).   For the filling recipe, I had been searching recipes online and found various types of recipes for homemade peppermint patties.  In addition to peppermint extract and confectioner’s sugar, some recipes called sweetened condensed milk, others for evaporated milk, and still others for egg whites and/or corn syrup.  Since I have a weakness for sweetened condensed milk (yum!), I decided to start with that and added a bit of flour to help thicken the filling and give it some body (hopefully).  I chilled the filling in the refrigerator to make it a bit easier to work with, then got to work assembling the cookies.  The technique: a larger chocolate dough ball was flattened with fingers and wrapped around smaller mint filling ball, pressing to seal the edges together, then the assembled cookie was placed on cookie sheet and flattened slightly with palm of hand.  After baking, my results were… mixed!  The cookies tasted pretty darn good, but almost all of them had the filling oozing out of the sides of the cookie.  We had some guests here at the B&B at the time and they were more than happy to serve as taste-testers and help try to troubleshoot the problem.  One quick attempt to improve the oozing problem was to make the cookie more like a thumbprint cookie by sticking the filling in a well created in the top of the chocolate dough.  Unfortunately, this didn’t quite work either – some of the fillings just flowed over the top like lava from a volcano and even those where the filling stayed put just didn’t have the right “look”.  Results so far:  chocolate cookie – good, mint filling – needs work.

The thumbprint-style ones are at the back of the cookie sheet.

On to attempt #2!  If you spend any time browsing online recipe sites that allow comments, you’ll see that almost no one makes the recipe as listed.  Almost everyone makes some sort of substitution.  I’m the same… I often use a recipe to get started, but make changes based on what I have in the house to work with.  So for this recipe, I wanted to try the chocolate cookie dough with regular unsweetened cocoa instead of the Dutch-processed cocoa I had used in attempt #1.  Why?  Mostly because I can’t always find Dutch-processed cocoa in the local grocery stores so I would need to plan ahead to make sure I have it on hand, but I usually have regular unsweetened cocoa in the pantry or can get it without much trouble so it would make for an easier recipe.  What’s the difference between the two cocoas?  The Dutch-processed cocoa has been treated with an alkali (base) that removes (neutralizes) some of the natural acidic (bitter/sour) components of the cocoa.  It generally results in baked goods that are darker and more chocolate-y.  This cookie recipe was no exception.  The cookies came out OK with the regular unsweetened cocoa, but next to the ones made with the Dutch-processed cocoa, there was no comparison.  The Dutch-processed ones were richer tasting and just so much better.

Dutch-processed cocoa on the left, regular unsweetened cocoa on the right.
Focusing on the filling, for my second attempt I tried a different approach – a mixture of cream cheese, egg white, and flour combined with peppermint extract and powdered sugar.  In this case the filling looked pretty good.  It didn’t ooze out at all and it made a nice, bright white layer of filling inside the cookie, but the sugar in the filling had crystallized and was crunchy (not what I had in mind).
Looked good, but too much crystallization.
Next, I tried a sort of combination of the first two attempts – sweetened condensed milk with confectioner’s sugar and flour, with egg white – hoping that as the egg white cooked, it would keep the filling from oozing out, and that the sweetened condensed milk would still give the rich flavor and maybe prevent some of the crystallization.  The result: failure.  The filling was again oozing out the sides and the water from the egg white required so much confectioner’s sugar and flour to make the filling workable, that the result was just not right.  Another attempt with just cream cheese and confectioner’s sugar didn’t ooze, but it was too cream cheesey. 
By this point, I had a definite idea of the ideal filling.  I was looking for a filling that had some substance – it needed to hold its own and create a substantial, visible layer inside the cookie, but it also needed to be smooth and just a little gooey, almost like a soft caramel (and not too crystalline or too creamy).  I had also refined my assembly method.  Instead of wrapping one piece of dough around the filling, I made two circles of dough and sandwiched the filling in between – pinching the edges to seal, then pressing the outsides back in so they would not be too thin and burn in the oven.
Back to the kitchen… since I had not yet tried corn syrup in any of my versions, this was my next attempt.  Corn syrup is often added to recipes like caramel to keep the sugar from crystallizing, so I figured that a little bit of it added to the filling might help solve the crystallization problem (similar to what I assumed was happening with the sweetened condensed milk).  Variations with cream cheese and corn syrup gave mixed results depending on the ratios of cream cheese, corn syrup and confectioner’s sugar.  The fillings varied between oozy and caramel-y, but the corn syrup variations were difficult to work with (the uncooked filling never firmed up, even after sitting overnight in the freezer). 
So next I went back to the ingredients that seemed to show some promise… cream cheese (for a bright white filling with body) and sweetened condensed milk (for rich flavor and a bit of caramel texture), with just the right amount of powdered sugar and a little bit of flour (for thickening).  With just another try or two, I had it!  (Or, at least I was really, really close!  Please see additional notes* below.)

So here’s the recipe again:

I didn’t take any photos of making the dough and filling, but I did take some of the assembly process to hopefully help understand it.
Assembling and baking cookies:   (See photos below)
Preheat oven to 350F  Remove dough and filling from refrigerator.  (Note: Both dough and mint filling will still seem somewhat sticky.) Using a cookie scoop or two spoons, scoop the dough into generous well-rounded tablespoons.
I used two cookie scoops to portion out my dough and filling.  The larger one, for the dough, is marked “50” (meaning 50 scoops per quart), the smaller one, for the filling is marked “100”.
Portioning out all of the chocolate dough should give you 26 scoopfuls for 26 cookies.
Roll each tablespoon of dough into a ball, divide each ball in half, and then flatten each half into small circles of 2 – 2 ¼”  in diameter.  Using a cookie scoop or two spoons, scoop a scant teaspoon of filling on to one of the dough circles.  Do not flatten the filling.
Place the second dough circle on top of the filling and pinch the outer edges to seal.
For some reason, this photo reminds me of a cartoon clam!  All it needs are some googley eyes!
While holding the cookie in hand, squeeze the outer edges in (so the cookie looks more like a hockey puck than a ravioli).
See… hockey puck (sort of),  not ravioli.
Place cookies on a Silpat or parchment-lined baking sheet and bake for 10-12 minutes, until the surface of the cookie looks smooth and evenly cooked.  Cool several minutes on baking sheet before transferring to wire cooling rack.
The baked cookie…
… and lots of baked cookies!
Optional:  Decorate cookies by dipping half in melted chocolate and/or drizzling melted chocolate on top.  I like Ghirardelli Candy Making and Dipping Bars – Double Chocolate Flavor for dipping and White Chocolate Flavor for decorating.  (These are available from Sam’s Club for a good price during the holiday season.)  I also tried semisweet chocolate chips, melted with a little bit of vegetable shortening.  It worked, but the flavor of the semisweet chips was pretty strong so it might be better with milk chocolate chips or a mix of the two.
Cookies half-dipped in chocolate.
Practicing with the white chocolate.
After practicing with squiggles and trying a snowflake (which was too difficult with melty, drippy chocolate), I decided to go with a stylized tree design.
All the cookies for the Cookie Tour, well over 200!

*Note 1: With regard to the filling, it seems like the balance between the cream cheese and sweetened condensed milk and the confectioner’s sugar needs to be just right to keep the filling from getting crystalline in the finished cookie.  When the cookies were made for the cookie tour, most of the filling in the finished cookies seemed just right, but some of the batches got a little crystalline.  I suspect it is because the filling recipe is hovering very close to the line between “ideal” and “crystalline”.  For future versions of this recipe, I may try to up the amount of cream cheese just a little bit and decrease the confectioner’s sugar ever so slightly to ensure a smoother filling.
*Note 2:  Don’t want to open a can of sweetened condensed milk just for this recipe?  You can substitute corn syrup, but as noted above, the uncooked filling will be much softer and stickier and you’ll need to work carefully and quickly to get it sealed inside the chocolate dough.
*One more thing:  Not sure what to do with the extra sweetened condensed milk?  There are lots of recipes at the Eagle Brand products website, but one of my favorite uses is to make Vietnamese Café Sua Da, iced coffee made with sweetened condensed milk.  Technically, you are supposed to use very strong hot coffee (like an espresso), mix with the sweetened condensed milk, then add lots of ice, but I usually just use cold coffee (from the morning) with a couple of tablespoons of the sweetened condensed milk and just a little ice.  Mmmm… it is like a dessert for me!  You could also make Dulce de Leche.  It is usually a very slow process, but I found a microwave recipe at a blog called The Perfect Pantry .
Now what?  Just writing this has inspired me to get working on alternate fillings… I’m thinking a caramel or caramel & pecans filling… and maybe cappuccino cream… and ??? 
See you in the kitchen!