Hey there, @Kurt8. 

Thanks for reaching out to the Community. 

To clarify, are you using QuickBooks Email or webmail? I recommend changing the email to use webmail. You can follow the steps below to do this. 

1. Click on the Edit menu, then choose Preferences. 

2. From the left pane, select Send Forms then My Preferences. 

3. Click on WebMail, then Add. 

4. Type in your email and choose your email provider.

5. Hit OK to save.

6. Hit OK on your Preferences menu.

7. Try sending an email. It will ask you for your Email password.  

You can see the details outlined in Connect your email to QuickBooks Desktop. 

Let me know if you have additional questions or concerns. I'll be here every step of the way. You can always reach out to the Community or me anytime you need a helping hand in getting back to business. Take care and enjoy your day!