Preheat the oven to 350F. Line 2 large baking trays with parchment paper or silpat baking mats.
Whisk together the butter and sugar together in a large bowl. Whisk in the molasses, vanilla, and egg until well-combined. Stir in the flour, salt, and baking soda, and then the chocolate chips.
Use a 1.5-tablespoon scoop to measure out the dough and arrange the balls evenly on the prepared trays. Bake until the cookies are set and light golden on the outside but still look a touch soft in the center, about 8 to 10 minutes, rotating the trays once halfway through.
Let the cookies cool to room temperature.
Assemble the Ice Cream Sandwiches:
Match cookies of similar size/shape into pairs. For each pair, top the bottom of 1 cookie with a scoop of ice cream, and then place the matching cookie on top of the ice cream scoop. Gently press down to spread the ice cream out.
Place the cookie sandwiches on a plate and freeze until the ice cream is set, about 20 minutes. (Unless by some miracle your ice cream is still solid enough that it isn’t dripping all over at this point. I live in Florida, so I needed the chill time before rolling the ice cream in sprinkles.)
Decorate with Sprinkles (Optional):
Roll the ice cream in sprinkles or mini chocolate chips if desired. Enjoy or freeze for later!
Notes
Recipe Yield and Serving Size: This recipe makes 20 cookies, which is enough for 10 ice cream cookie sandwiches. Each serving is 1 cookie sandwich.
Nutritional Information: The nutrition information for this recipe was calculated without the optional sprinkles or mini chocolate chips.
Storage: Store these well-wrapped in the freezer for up to 3 months. I wrap each individually in plastic wrap or freezer paper, and then place them in a zip-top freezer bag or airtight container.
Ice Cream: Let the carton of ice cream sit at room temperature for 10 minutes to soften it slightly before making the cookie sandwiches.
If Your Cookies Are Cracking or Breaking When You Make the Sandwiches: Lay the cookies flat so they’re not touching on a parchment-paper-lined baking tray and freeze until solid, about 20 minutes. I usually bake these cookies the day before I make the sandwiches, which avoids this because they have time to cool fully and stiffen slightly. Serving Tip: After being in the freezer, let the cookies sit at room temperature for a few minutes before eating to soften slightly.