This is my favorite pumpkin pest. His name is Anasa tristi, or, Mr. Squash bug.
I’m fully convinced that they’re named “squash bugs” because that’s what I do with them after I pull them off of my pumpkin plants. I throw them on the ground and punch them hard enough to make Mike Tyson proud. I immediately bury them under dirt because they have a very noxious bitter smell after they’re squashed.
My daughter and I inspect the plants every morning and evening looking for these little punks and looking for any eggs they may have laid. The nymphs are worse than the adults in terms of the damage they can do to your precious plants. I remove the eggs using sticky packing tape. I find that scotch tape isn’t quite sticky enough to grab them all at once.
They like to lay the eggs on the bottom side of the leaves close to the stem, sometimes even on the stem itself. you must remove them and destroy them.

Destroy these creatures and their eggs with extreme prejudice. If they get a foot hold on your pumpkin patch, not only will your plants suffer, but the bugs like to overwinter under the soil and in any nook or cranny they can find, and the next year, you immediately have a squash bug infestation from the get go. If you plan on using your pumpkins for baking, or making pumpkin beer *yummy!*, FORGET IT! Squash bugs will make everything taste like fermented piss. Kill them at every opportunity.
DESTROY, DESTROY, DESTROY!

Now about prevention. I have found that if you take some peppermint castile soap, dilute it in a small spray bottle according to the directions, and spray the underside of the pumpkin leaves and the center of the plant and stems, the bugs don’t like it much. If the plant is flowering and bees are doing their job, be careful around the male and female flowers. You don’t want to drive away our best buddies, the bees, or as my daughter calls them, “fuzzy buzzy’s“. We love our fuzzy buzzy’s. ❤️🐝
Check for squash bugs and their eggs every day, twice a day, especially while the plants are still small, and your pumpkins will thank you.
Good luck!