Hi Jeremy Tschetter,
Thank you for reaching Microsoft Community. Apologies for the inconvenience this has caused you.
Just to make sure that I get the exact picture of the concern: previously, you are able to select multiple pdf files in File Explorer then right-click and select Print then it prints out to the printer until the recent updates, correct? Or you still able to do these steps but the printer wont print the files selected?
If possible, kindly provide us with a screen recording of the issue that you are experiencing in trying to print multiple pdf files and share it with us here.
May I know also what Windows Edition, Version and OS Build is your Surface Pro 7 running? To check, you may go to Windows Settings > System > About.
What is the make and model of your printer?
I'd love to provide you with the troubleshooting steps right now to fix the problem. I am afraid that we may have to wait for the above answer first so that we can provide the necessary information. Once we collect all the information, we will formulate the feasible resolution to help you with your case or if we need you to refer to the support that suits your problem.
Kind regards,
Marrion