I'm am going to be making tombstone cupcakes for Halloween using Milano cookies for the tombstone.  Question, should I cut a small slit in the cupcake to insert the cookie easier or just gently push in?  This is my first time and I don't want to accidentally end up smushing the cupcake trying to get it in.

You can do it either way, but I prefer to cut a small slit because the cookies tend to fall over, and it gives it a little more stability. I always do a light coating of icing then sprinkle crushed oreos for dirt, so it really has nothing to hold it in place.

That's my plan too with the frosting and "dirt".  I'm also adding some skull and bone mini candies I found from Wilton.  Plus a worm.  I can't wait to see them!  :)  

Thanks!

Those sound super cute, in a creepy way lol you're welcome! 

Please be forwarned......though I have not used that exact cookie, others have absorbed moisture from the cake overnight and fell over/broke.  This is something I think must be done at the very last minute.

I usually make them the night before and would have cried.. hahaha.. I will stick the cookies in right before we leave.  Thanks for the tip!