Hello, @briansosclean. 

Thanks for following the thread and sharing your concerns. I'm happy to lend a hand with your Yahoo email. 

When using Yahoo mail in QuickBooks Desktop, you'll need to complete a two-step verification to allow apps that use less secure sign-in features. Let me walk you through the steps to turn this on from Yahoo. 

1. Go to your Yahoo Account Security page.
2. Turn on the Two-step verification and Allow apps that use less secure sign in features.
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3. Once the feature is turned on, go back to QuickBooks and test an email. 

If for some reason you're still experiencing issues with sending email from QuickBooks, check out Yahoo's generate third-party app passwords tool. This tool will create a random password you can use to connect to QuickBooks. 

You can see additional details in Fix webmail password issues in QuickBooks Desktop. '

Please let me know if you continue to have issues sending emails. I'll be here every step of the way. You can always reach out to the Community any time you need a helping hand. Take care!