I'll ensure to get the error sorted out and successfully file 1099s.
May I know the steps you took when you encountered the error messages? We'll need this to check if there are any reported issues regarding this matter.
However, I suggest contacting our Technical Support Team to investigate further the issue in a secure space. Also, you can request a screen-sharing session with them to guide you in successfully filing 1099s in QuickBooks.
Here's how:
Go to Help.
Select Contact Us.
Enter your concern in the What can we help you with? section.
Click Continue.
Choose a channel where you want to connect with our specialists.