Hello, @tbass3321.
Make sure to have the latest release of your QuickBooks Desktop. This will keep your software up-to-date so you always have the latest features and fixes.
If you still get error messages, try to check AOL’s email settings. Make sure that QuickBooks isn't blocked.
If the error persists, go to your antivirus settings and allow port exceptions. Here are steps for Norton and McAfee.
- Make Port 465 open for Yahoo! Mail.
- Make Port 587 open for Gmail and all other email services
Once done, go back into QuickBooks and email yourself a test transaction.
Read this article for more information: Fix webmail password issues in QuickBooks Desktop.
I'm always here if you need help. Have a wonderful day!