Hi, @mnalaboff.

This isn't the kind of experience I want to you have when sending invoice emails from QuickBooks Desktop (QBDT). I want you to know that our engineers are already looking for a fix so you can send emails to Outlook seamlessly. The investigation (INV-0671) is still open and in progress, if you haven't yet, I recommend reaching out to our Support Team to add your name to the list of affected users. Once added, you'll automatically receive an email notification of the recent updates.

Additionally, you can update QuickBooks manually or automatically to get the latest features and fixes.

For now, you may set up and temporarily use webmail in sending your emails through QuickBooks.

Here's how:

1. Go to the QuickBooks Edit menu and click Preferences.
2. Click Send Forms.
3. Under the My Preferences section, select WebMail.
4. Enter your email address and select your provider from the Email Provider drop-down.
5. Select the Use Enhanced Security checkbox and select OK.
6. When prompted, sign in to your Intuit account.

You can also check out this article for more information: Connect your email to QuickBooks Desktop.

Please let me know if you have any other questions while sending emails from QuickBooks. I'll be right here to help. Have a good one!