Which 1099 form type are you selecting in the task and what form type is selected on your vendors in Setup > Vendors > 1099 Settings tab? And are they marked to receive a form 1099?

You can run the 1099 Preparation report to verify your vendor setup and amounts (AP Reports > Miscellaneous > 1099 Preparation)

We are using the 1099 Misc form type and they are marked to receive a form 1099.  We did run the 1099 Preparation report and since we are cash basis, we also ran the check register by property for 2021.  They matched.

Make sure in Setup > Vendors on the 1099 Settings tab that the vendors have the 1099-MISC form type selected and not one of the other types. Here's an example from sample data:

This is how it's set up.

You're on an old version. You need to be on version 20.3 or newer because the 1099-NEC forms were introduced in 2020.

Thanks!  I see about updating.