Thumbprint Cookies with Chocolate Filling

Lately I've been alternating between recipes from the box that are so easy they don't even properly deserve to be called recipes (I'm looking at you, beer bread and the upcoming tomato soup recipe I'm sharing later this week) and dishes that, strictly speaking, include multiple recipes just to get to a finished product. This is one of the latter.

I've said already that I'm not wild about melting chocolate. I find it to be a really fickle project, and for every batch of chocolate I've successfully melted, there's another one out there somewhere that I've either burned or seized. Luckily, so far with the box, there have been no major incidents (but that doesn't mean I love the process)... until now.

I made these cookies for Judson to take to work for a game night he and some friends organised, and I was super excited about them because the cookies are supposed to be filled with “jam, citrus peel, or chocolate,” and I recently found a recipe for “chocolate filling for cookies,” so I got to use two recipes at once this time. (The recipe card for the cookies is worn and stained with Eleanor's notes in the corner, so I know she made these a lot. The chocolate filling recipe looks practically brand-new, so I don't know that this is what she used to fill the cookies, but we liked them pretty well.)

Eleanor wasn't pretentious enough to call the filling of these cookies ganache, but that's more or less what it is. It's the same chocolate mixture I used in the Chocolate Key Lime Pie from earlier this week, because I made these cookies first and was so excited about the results. Anyway, I was anticipating disaster, but sometimes it turns out if you follow a recipe to the letter, good things WILL happen.

These cookies are perfect cocktail party food: they look supremely fancy, they're rolled in nuts to give them a nice toasty flavour, and the rich, smooth, almost bitter chocolate filling contrasts really well with the sweet and crumbly shortbread texture of the cookies. You could fill them with jam, lemon curd, or candied citrus peel, but I think the chocolate is the most elegant/least messy of those options (and you know how we love elegance in this house. Ahem.).

The recipe seems overly detailed, but I'd encourage you not to skip the step of rolling the cookies in egg whites, even if you skip the nuts: the whites help give the cookies some body and keep them from splitting apart as they cook-- important since you'll have to press down the centers while the cookies are still hot. The recipe only makes about 16 cookies, so this is the perfect treat to bring to a friend's house to nibble with coffee, though it's easy enough to double it (and evidently, Eleanor often did, as she scribbled in the doubled amounts next to the original ingredients). Plus, I've now made this chocolate filling twice, with two different types of chocolate and two different procedures, and it's come out beautifully each time. If I can do it, so can you. Good luck!

The Verdict:

4 Spoons out of five. The cookies are straightforward enough, if a bit detailed, and the chocolate filling is surprisingly foolproof. They're rich enough and the chocolate is dark enough you're not going to want more than one at a time, so make them for a party or to go with coffee, not to get a major sugar rush.

The Recipe:

Thumbprint Cookies with Chocolate Filling

The Ingredients:
The Cookies:

½ c shortening (or Stork, if in the UK), softened
¼ c brown sugar
1 egg, separated
½ tsp vanilla
1 c sifted flour
¼ tsp salt
Finely chopped nuts (I used a mix of almonds and pecans)





The Filling:

1/3 c sugar
1 tbsp milk
1 tbsp butter
1 tsp vanilla
1 egg, beaten
6 oz. semi-sweet chocolate
Handful of whole pecans


Preheat oven to 375F/190C.
Mix shortening, brown sugar, egg yolk, and vanilla together in a large bowl.
Stir in sifted flour and salt (texture will be dry and almost like wet sand, but should stick together well).
Roll dough into 1-inch balls.
Dip in lightly beaten egg white, then roll in finely chopped nuts.
Place about 1 inch apart on ungreased cookie sheet.
Bake 5 minutes, then remove from oven and quickly press thumb or small spoon on top of each cookie to make a dip where the filling will go (if you figure out a way to do this without burning yourself, tell me how).
Return to oven and bake 6-8 more minutes until golden brown.
Let cool on a rack before filling.


Stir together sugar, milk, butter, vanilla, and egg in a bowl and set aside.
Melt chocolate in microwave at 10-second intervals, stirring after each interval until smooth.
Allow chocolate to cool slightly for about a minute, then pour in sugar mixture.
Stir constantly and quickly until mixture is smooth and glossy-- it may seize for a moment and get slightly grainy, but keep stirring briskly and it should smooth out quickly.
Spoon filling into each cookie's centre, topping with a whole pecan while still warm.
Filling will set and become semi-firm, but it will always be soft and fudge-like, not hard like a bar of chocolate.
(If you have any leftover filling when you've filled your cookies, dig around in your pantry and see what else you can dip in chocolate-- I used some clementines and a handful of saltines to finish up my chocolate-- yum!)

Yields approximately 16 cookies