Place a medium cutting board or flat plate that is freezer safe (and fits into your freezer- check this before starting!) on the counter. Next, place two long pieces of plastic wrap in a cross over the cutting board.
Trim the edges of your ice cream sandwich cookie base if desired then cut in half. GENTLY slide one half into the middle of your cutting board/plastic wrap.
Scoop 1-1.5 pints cherry ice cream over the cookie. Work gently to spread it evenly over the cookie base and use as much or as little ice cream as you want. I like about an inch thick of ice cream.
Adding the top part of the cookie is hard since it is fragile, but do your best to flip the other half of the cookie base onto the top of your ice cream. Line everything up then tightly wrap up the sandwiches in the plastic wrap. Wrapping tightly holds everything together while the ice cream is soft. The plate/cutting board provides a sturdy support as the sandwiches freeze.
Place the sandwiches in the freezer for at least 4-6 hours, preferably overnight to allow the ice cream to fully set.
When ready, slice into 8 sandwiches.
I like to wrap each sandwich individually in plastic wrap or parchment paper then store in a freezer safe bag or container until ready to eat. Pull one out on a hot summer afternoon and enjoy!