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Emailing from Quickbooks Enterprise 18 through Outlook 2016 O365 on a 2008R2 Terminal Server

We recently turned on MFA on O365 for our client.  They were previously (and successfully) using Office 2010 installed on a terminal server (Quickbooks is installed on the physical server the terminal server runs on) to email invoices from Quickbooks.   Upon turning on MFA, we learned that Office 2010 will not work with MFA so we went ahead and uninstalled 2010 Office and installed 2016 Office Shared Activation through their Office 365 (each user also has an E3 license).  We had the users sign into Outlook 2016 on the terminal server under each of their profiles and that was successful (including the MFA).  Outlook 2016 is set up as the default mail for each user's profile as well.  This worked fine for about half a day and then we began getting messages in QB that the email could not be sent, we could not open Outlook, etc.  We reinstalled QB and repaired Office.  We also removed QB and reinstalled Office then installed QB but no luck.  Any ideas appreciated!

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QuickBooks Team

Emailing from Quickbooks Enterprise 18 through Outlook 2016 O365 on a 2008R2 Terminal Server

Thanks for reaching out to us here in the Intuit Community, @newrivercomputing.


I appreciate you performing some troubleshooting steps to get this resolved.


One of the reasons you're getting this message is when you run QuickBooks as administrator. It's also possible there's another Outlook open in the background when sending invoices.


Make sure to close any open Outlook program, then QuickBooks is not running as administrator of the Outlook:


  1. Right-click QuickBooks Desktop icon, then select Properties.
  2. Go to the Compatibility tab.
  3. Unselect Run this program as Administrator.
  4. If Run this program as Administrator is grayed out, select the Show Settings for All Users.
  5. Click OK, then Exit.
  6. Make sure to restart the software.

If the same issue persists, you can try to perform other troubleshooting steps outlined in this article: Error QuickBooks is unable to send your email to Outlook.


I also suggest checking out the system requirements for needed for your version. This is to ensure the Outlook version is supported by the program.


Please keep me posted on how this goes. I'm always around whenever you need further assistance emailing invoices.

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