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These cookies are my grandfather’s favorite iced chocolate cookies! They are an old family recipe for pillowy soft, cakey cookies iced with a tasty chocolate icing.


So there’s sort of a non-story story behind these cookies. I’m sure there are actually plenty of memories around them given that they were my grandfather’s favorite, but they aren’t my memories. I never actually met my grandfather. He passed away when my mom was a teenager.
So how do I know they were his favorite?
Well when I was texting my mom several weeks ago to ask her for the cutout sugar cookie recipe we used to make when I was a kid, she got on a kick and started sending me all kinds of cookie recipes and this was one of them. They were actually titled “Jack’s Favorite Chocolate Cookies”. I knew immediately I’d be making them.


I didn’t really know what they’d be like from reading the recipe card. It was typed with a typewriter onto an index card, so there wasn’t exactly a photo. 🙂
Turns out they’re delicious! Not that I really doubted. They are super soft and cakey. They are then topped with an icing made with milk, powdered sugar and melted chocolate. Very simple to make and quite tasty. The icing also gets nice and firm so they actually stack in a container pretty well with parchment paper between them.
I asked my mom about the cookies and my grandfather when she visited this past weekend and she laughed as she remembered how much her father loved the cakey-ness of them and how the icing makes them even more cake-like.
I had so much fun making these and thinking of my grandfather. Though I never met him, I feel like I know a very small part of him after trying his cookies. They might just have to become a Christmas tradition.


More Chocolate Cookie Recipes
- Double Chocolate Cookie Sandwiches
- Turtle Chocolate Cookie Cups
- Nutella Cheesecake Chocolate Cookie Cups
- Reese’s Peanut Butter Chocolate Cookie Sandwiches
- German Chocolate Cookie Stacks

Grandfather’s Favorite Iced Chocolate Cookies
- Yield: 28-30 Cookies
- Category: Dessert
- Method: Oven
- Cuisine: American
Description
This recipe for my Grandfather’s Favorite Iced Chocolate Cookies is an old family treasure! The chocolate cookies are pillowy soft, cakey and topped with a tasty chocolate icing.
Ingredients
Chocolate Cookies
- 1 cup (208g) sugar
- 1/2 cup (112g) salted butter, room temperature
- 1 large egg
- 1/2 cup (120ml) milk
- 1 1/4 tsp baking powder
- 1 1/2 (195g) cups all purpose flour
- 3 tbsp (22g) unsweetened natural cocoa powder
Chocolate Icing
- 2 cups (230g) powdered sugar
- 4–5 tbsp (60-75ml) milk
- 4 oz semi-sweet chocolate chips, melted
Instructions
- Preheat oven to 375°F (190°C).
- Mix sugar and butter just until combined and smooth.
- Add egg and milk and mix until smooth.
- Combine dry ingredients in a separate bowl, then add to wet ingredients. Mix until well combined.
- Drop heaping tablespoons of cookie dough onto lined cookie sheet.
- Bake for 8-10 minutes, then remove to cool. Allow cookies to sit on cookie sheet for 2-3 minutes, then remove to cooling rack.
- Once cookies are baked and cooled, combine powdered sugar and milk for icing. Add the melted chocolate then spread onto cookies.
- Cookies can be stored at room temperature for 4-5 days or be frozen for up to 3 months.
Nutrition
- Serving Size: 1 Cookie
- Calories: 127
- Sugar: 15.7 g
- Sodium: 30.3 mg
- Fat: 4.4 g
- Carbohydrates: 21.4 g
- Protein: 1.5 g
- Cholesterol: 14.5 mg
Enjoy!