I have been banging my head against a wall with this same issue. 1096 no problem. 1099 no bueno. Exactly the issue Jessjesscpa is having. Willing to be she signed up yesterday just to report the issue...ME TOO! This is something that has been working for years and suddenly broken. Need to get the 1099's printed.

QB Pro 2021

Tried the suggestion to enable Share updates.

Ran Print & PDF repair

Ran check windows files

Rand check database integrity

Thanks in advance for boosting this up to someone who can fix it.