Hello there, @JHawkins344.
 

Thanks for reaching out to us here in the Community. I appreciate you for taking the initiative to perform some steps to resolve the issue. I'm here to make sure you can get that email going.
 

Have you updated your QuickBooks Desktop to its latest release? Keeping your software up-to-date helps you always have the latest features and fixes. 

Here's how:

1. Go to the Help menu and then Update QuickBooks Desktop.
2. Under the Update Now tab, select the Reset Update checkbox to clear all previous update downloads.
3. Click Get Updates to start the download.
4. When the download finishes, restart QuickBooks and accept the option to install the new release when prompted.

Once done, launch the QuickBooks and try sending test emails to yourself. If you continue to get the same error, I recommend reaching out to our Customer Care Support team. 

1. Select QuickBooks Desktop Help from the Help menu.
2. Click Contact Us.
   
3. Type in a short description of your concern, then Continue.
4. Choose a way to connect with support.

I'm sure that an agent would be happy to assist you with any questions that you have. For more details about our support availability, refer to this article: Contact Support. 

You can also turn on the automatic update to make sure that your QuickBooks Desktop is always updated. Please check this article and follow the Schedule future automatic updates steps: Update QuickBooks Desktop.

Visit me here again in the Community and keep me posted on your progress with sending paystubs to your employee. I'm determined to help you succeed.