Hello, @Angie13.
I can see that you've been through a lot trying to send invoices and estimates from QuickBooks Desktop. I appreciate you for bringing your concern to our attention. I'm here to help you today so you can send your forms seamlessly again.
Usually, there are several factors why you experience difficulties emailing forms through QuickBooks. Here are the following:
- The email preference being set incorrectly.
- A damaged QuickBooks installation.
- The domain admin was blocked.
- Account security settings from your email provider.
To narrow down the cause of the issue, let's make sure your QuickBooks Desktop software is in its latest release. Once done, you can check the webmail settings in the preferences.
- Choose Preferences from the Edit menu at the top menu bar.
- Click Send Forms on the left panel.
- Under My Preferences tab, select the email account you're using.
- Click Edit.
- Mark the SSL box, or just select Default.
- In the Server Name field, make sure the server name matches your email provider's settings.
In the newer versions of QuickBooks, you can also use a Secure Webmail for an easier and safer connection to your email provider. You can check out the details from this article for your reference: Connect your email to QuickBooks Desktop.
Right after, try sending the invoices again. For more related resources, feel free to read the information from this link: Error: Could not connect to the email server.
Please let me know in the comment section if you have any follow-up questions. I'm here to help and answer them for you. Have a great day and keep safe always!