Hi there, Kelper. Thank you for your efforts in trying to resolve your concern. I genuinely appreciate your proactive approach. Let me give some clarity on why you were prompted with a Webmail Authorization window. 

Please note that we removed the screenshot containing your e-mail address for privacy purposes, as the Community forum is a public space.

QuickBooks Desktop (QBDT) allows you to send e-mail communications through Web Mail, Outlook, and QuickBooks e-mail.

The appearance of a Webmail Authorization window in QBDT could be due to security updates implemented by Outlook at that time. These are part of an ongoing effort by e-mail services to enhance the security and protection of user accounts from potential threats and unauthorized access. To maintain a high level of security, you need to undergo a reauthorization of your credentials.

Dropping a comment below is the easiest way to get in touch with our friendly Community experts. I'd be glad to address additional questions you may have about managing e-mail preferences in QBDT.