Hello, @cjapeacock! Maintaining a smooth workflow is essential, especially after years of experience with QuickBooks and Outlook. It’s natural to feel a bit thrown off when things don’t go as planned, but we’ll get this sorted out together.

It looks like recent Outlook security updates are causing the Webmail Authorization window to appear. This is a necessary step to maintain the security of your account. Here’s how to reauthorize your Outlook in QuickBooks:

1. Update QuickBooks Desktop to the latest version.
2. Open any transaction or report and click on Email.
3. Click Send, and log in using your Intuit credentials if prompted.
4. In the Webmail Authorization window, click Continue, then select Allow.

If you’d prefer to use Google email for sending invoices, you can find more information in this article: Connect your email to QuickBooks Desktop.

For detailed steps on authorizing your Gmail or Outlook account and adjusting security settings, check out these guides:

• Reauthorize QuickBooks Desktop to use Outlook and Gmail.
• Set up enhanced security in Gmail for QuickBooks Desktop.

We’re here to assist you with any email or accounting questions. If you need more help, don't hesitate to reach out to the Community. We're always ready to support you!