Hello there, SAaccountant.  

After the updates, you should be able to prepare and print your 1099s with the three tax forms per page. We can reset the update and check if it already available.   

Here's how:   

1. From the QuickBooks dropdown, select Check for QuickBooks Updates.
2. If a newer version is available, select Install Update.
3. When prompted, select Install and Relaunch.
4. Once complete, QuickBooks for Mac automatically opens.

Then, update the QuickBooks Server for Mac

1. Go to QuickBooks [year] Server next to the Apple logo.
2. Click Check for Quickbooks Server updates.
3. Select Install Update.
4. Click Install and Relaunch.

You can use this article as a reference on how to create you 1099. Just click the section and then scroll down to QuickBooks Desktop for Mac: Create and file 1099s with QuickBooks Desktop.  

If the same thing happens, I suggest reaching out to our Phone Support Team so they can perform advanced troubleshooting steps.   

Fill me in if you have further questions about updating your 1099 in QuickBooks. I'm just a post away and willing to help you in any way I can.