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Hi there, @Anonymous.
I appreciate you joining this thread and trying some tests in order to resolve your concern. I can help you more with sending the invoice transactions through email.
QuickBooks Desktop doesn't use your email password when sending invoices. Rather, it needs the random password given during the 2-step verification process.
Here's how to generate 3rd-party app passwords:
- Sign in and go to your Account security page.
- Scroll-down to the Two-step verification and Allow apps that use less secure sign in sections and turn on both features.
- Follow the prompts to get a one-time app password: Generate third-party app passwords.
Next, try sending the invoice through QuickBooks Desktop again. In the Password text box, enter the third-party app password generated by Yahoo and click OK.
For in-depth information, you can use this link as a reference: QuickBooks will not accept my web mail password.
Let me know how these steps work out for you, CFisher. Just click the Green (reply) button to leave a message for me. I'll be here to keep helping.