I just spent 2 hours on a chat to figure out why I can no longer send forms via email from QuickBooks. There was no resolution. I did some checking with Google, my email provider, and apparently Google has an issue with security with sending forms from QuickBooks. Other than creating a separate PDF and emailing directly from my Gmail account has anyone found an easier way to email invoices, estimate etc directly from QuickBooks?
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.
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.
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.