Thanks for reaching out to us on this thread, @njdavis7. I appreciate you for sharing the steps you've done before contacting us. 

To make sure I'm giving you the right fix, I want to know if you receive any error messages when emailing your invoices.

In the meantime, I recommend updating QuickBooks to the latest release. Here's how: 

1. Go to the Help menu at the top right, then select Update QuickBooks Desktop on the drop-down.
2. On the Options tab, click Mark All, then Save.
3. Now, go to the Update Now tab and mark the Reset Update box, then select Get Updates.

After that, check the web mail’s settings in the Preferences section. Here’s how:

1. Go to the Edit menu and choose Preferences.
2. Click Send Forms., then choose Outlook under My Preferences tab.
3. Click Edit.
4. Mark the SSL box or set it to Default.
5. In the Server Name field, make sure the name matches with what’s on your email provider’s settings.

That should get you back on track. You can also save these artcles for your reference: 

• Set up an email service.
• Error: Could not connect to the email server.

Let me know how this goes and if you need anything else. I’ll be on the lookout for your response. Take care!