Hello there, @fishmanbill.
When emailing transactions such as invoices from QuickBooks Desktop, you will be prompted to enter your Web Mail Password. This is the actual email password that you’re using outside QuickBooks. (e.g. Gmail password, Yahoo password, etc).
If you see a message about an incorrect email or password, updating your QuickBooks to the latest release is a good start to isolate issues like this.
If the issue persists after the update, open your online email service. Review your settings and filter preferences. These may be accidentally blocking your emails from QuickBooks. To give you more insights on how to do this depending on the email provider that you're in, please see this link: QuickBooks isn't accepting my webmail password.
Let me know how these steps work out for you, fishmanbill. Just leave a reply below and I'll get back yo you. Have a good one!