Hi Patty,

Let me join the thread and provide some clarifications.

You don't need to switch the settings from Outlook to Webmail to enable the auto-populate email later checkbox when creating batch invoices. All you need to ensure is that the customer's preferred delivery method is set to Email, and the "Auto-check the Email Later checkbox if customer's Preferred Delivery Method is Email" option is checked in the Preferences.

To further troubleshoot the issue you're experiencing, we can review the user role setup to ensure it's configured correctly. For more details on this, you can refer to this article: Create and manage users and roles in QuickBooks Desktop Enterprise.

Meanwhile, since everything is set up on your end and you've already performed data damage troubleshooting steps but the issue persists, I recommend creating a dummy or sample company file and replicating the same setup for the customer and preferences.

However, if the same thing happens with the new setup, proceed to Solution 2 in this article: Fix data damage on your QuickBooks Desktop company file.

If you have any further questions or other concerns, Patty, please feel free to reach out. I'm here to assist you.