Thanks for joining this thread, KChassie.
 

Since Outlook isn't sending emails through QuickBooks, I'd initially recommend confirming that Office 365 is up-to-date with Microsoft's latest release.
 

Here's how:

1. Open Outlook, access your File tab.
2. Choose Office Account, then use the About Outlook button. Make sure you're using Microsoft's latest release (12527.20242). If you need to update, click Update Options.
3. Select Update Now.

Now you can return to QuickBooks and try emailing your transaction and/or report again. In the event you're still unable to send emails using Outlook inside of QuickBooks, you'll want to edit your admin privileges:

1. Close QuickBooks and open the Windows Start menu.
2. Type "QuickBooks" into your search bar, then right-click the QuickBooks app icon and choose Open file location.
3. In its folder, right-click QuickBooks.exe and pick Properties.
4. Access your Compatibility tab.
5. Untick the Run this program as Administrator option. If this option is grayed out, hit Show Settings for All Users, then untick its checkbox.
6. Press Apply, then OK.

Once you've finished editing your admin privileges, you can try emailing again. If it's still giving problems, you can move on to editing the email preferences in QuickBooks.
 

I'll be here to help if there's any questions. Have a great day!