Thanks for swinging by the Community, Tony.

Allow me to point you in the right direction to prevent QuickBooks Desktop (QBDT) from crashing when emailing invoices to customers.

I admire you for performing the shared steps above to resolve your concern about being unable to send invoices via Outlook. Getting back and forth isn't easy. Thus, it's best to reach out to our customer support for further assistance. They have access to a screen-sharing tool that will determine the root cause of the issue and may raise an investigation if need be. 

Furthermore, there are a few ways you can take and process payments in QBDT. You may either turn on online payments for the invoices you email to customers or process them in person.

You can always get back to us if you have more questions about emailing invoices. We're always here to assist you further.