Quickbooks Premier 2018 R14P issue with Outlook

Hello there, @kjthewicked.

If you receive an error message "QuickBooks is unable to send your email to Outlook", this is usually a settings issue. Follow the steps below so you can send emails from QuickBooks. Also, I'd suggest seeking assistance from an IT professional to help you further with this.

Step 1: Edit your admin privileges

1. Close QuickBooks Desktop.
2. Open the Windows Start menu.
3. Type QuickBooks into the search button. 
4. Right-click the QuickBooks icon and select Open file location.
5. In the folder, right-click the QuickBooks.exe file and select Properties.
6. Click the Compatibility tab.
7. Select to uncheck the Run this program as Administrator option.
8. Select Apply and then OK.

Once done, open your QuickBooks and send a test email or transaction. If you still get an error, move on to Step 2 using this link: QuickBooks is unable to send your email to Outlook.

In case you have any other QuickBooks concerns in the future, you may check our self-help articles: Help articles for QuickBooks Desktop.

If you need additional help, reach out to us by clicking the Reply button below. We're always here to provide further assistance with anything QuickBooks related. Have a great day!

Hello Maybelle - thank you for taking the time to reply. I apologize for the delayed response, but it has been a busy week for me.

So, I actually am an IT professional. I've gone through everything I can think of that may be source of the issue, and the only thing I cannot eliminate is QuickBooks and how it "invokes" a new email prompt when Outlook is not open.

Some more details:

If the user opens Outlook in a full remote desktop, then sending emails work fine 99% of the time. 

The failure specifically happens when Outlook is *not* open, so QuickBooks has to "invoke" a call to open the "new mail" dialog.

This works for the first email only - it is able to successfully send it. But if they attempt to send any more emails the same way after that, it fails because Outlook hangs after the first email.

It only happens with QuickBooks and I haven't been able to replicate it at all any other way.

I wish I could make it better, @kjthewicked.

Since you're still having issues with sending invoices via Outlook, I'd recommend contacting our Customer Care Support. They have the tools to further look into the account and can also create a case to be submitted to our engineers for further investigation.

1. Go to Help.
2. Select QuickBooks Desktop Help.
3. Click Contact Us.
4. Select Search for something else.
5. Enter Invoice issue with Outlook in the Tell us more about your question: field.
6. Click Start a Message.

In addition, here's an article you can read to learn more about our available support: Support hours and types.

Lastly, I've got you this helpful article for ideas about how you can manage your account and transactions: Help Articles for QuickBooks Desktop.

If there's anything else that I can help you with, let me know in the comments. I'll be happy to help.