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Level 1

QB Desktop Pro 2019 locks up when I try to email an invoice

We used to be able to email invoices, from Quickbooks 2019, through our Outlook/Office 365 email account. But that quit working several days ago. When I click SEND (on the Send Invoice dialog) Quickbooks just goes off into never-never land. I have to open Task Manager (Windows 10 Pro) and end the task. I have rebooted my PC, I have run a chkdsk C: /f on my PC's boot drive, I have done an Office 365 (2016) Quick Repair, I have the latest updates for Quickbooks 2019. I don't know what else to try. My settings for email are as follows:

Web Mail

Email: (our email address)

Email provider: others (office 365 is our email service)

SMTP details:

Server name:

Port:  587

SSL/TLS is checked


When we try using that (we have also tried as an alternate SMTP mail server) Quickbooks just stops. We get the little blue circle but nothing happens. It used to take about 10-15 seconds then we'd get the login dialog (if this was the first time using Quickbooks this session) and we'd put in the password and it would just work. But now...nothing! And no indication of why it's not working. Quickbooks does not seem to have a time-out feature and display an error dialog explaining why it's not connecting or sending. (poor coding, if you ask me)


Does anyone have a fix for this?

QuickBooks Team

QB Desktop Pro 2019 locks up when I try to email an invoice

Hi there, @ISDPCMAN.


I really appreciate that you're trying some of the troubleshooting steps that might help you fix your concern. I have some additional troubleshooting that could help fix the problem. This problem might be a settings issue. You can follow these steps in order so you can send emails from QuickBooks.


If you're experiencing log in issues with your Office 365, this error caused by an outdated Microsoft Office 365 release. To fix it, you can update your Microsoft Office 365 to the newest release version. Here's how


  1. Open Outlook, then select the File tab.
  2. Select Office Account, then the About Outlook button. Note: Make sure you see the latest release of build.
  3. Select Update Options and then Update Now to update the newest release.
  4. Go back to QuickBooks and try to email your report or transaction again.


If the issue persists, you can follow these next troubleshooting steps:


Step 1: Edit your admin privileges


Make sure QuickBooks isn't set to automatically run as an administrator.

  1. Close your QuickBooks Desktop application.
  2. Click the Windows Start icon at the toolbar.
  3. Type "QuickBooks" in the search, then right-click the QuickBooks icon and choose Open file location.
  4. Right-click the QuickBooks.exe file and select Properties in the folder.
  5. Choose the Compatibility tab.
  6. Select to uncheck the Run this program as Administrator option. If the option is grayed out, select Show Settings for All Users to make the option available.
  7. Click Apply and then OK.


Open your QuickBooks Desktop application and send a test email or transaction. If you still receive an error message or still cannot send an email, you can refer to this link for more troubleshooting steps: How to fix "Error: QuickBooks is unable to send your email to Outlook"


Tell how it goes and fill me in if you need more help by leaving a comment below. I'll be around in the Community to help. Take care and have a great day!

Level 1

QB Desktop Pro 2019 locks up when I try to email an invoice

I followed your instructions and it still locks up when we try to send email. I have to kill Quickbooks in task manager. 

QuickBooks Team

QB Desktop Pro 2019 locks up when I try to email an invoice

Hi there, @ISDPCMAN.


I'd like to ensure that you'll be able to send invoices in QuickBooks Desktop with no issues.


To get this problem sorted out, I recommend repairing QuickBooks. This can help fix program-related issues since the steps provided by my peer above didn't work. Before doing so, make sure to create a backup copy of your company file to prevent data loss.


Once done, you may follow these steps below:

  1. Restart your computer. This makes sure there are no programs that may affect the repair.
  2. Open the Windows Start menu, then press on Control Panel. If you're using Windows 8 or 8.1, search "Control Panel" in the Windows Start menu.
  3. Select on Programs and Features then Uninstall a Program.
  4. Hit on QuickBooks from the list of Programs, then Uninstall/Change.
  5. Tick on Continue, or Next.
  6. Click on Repair, then Next.
  7. After that, select Finish.

    Note: You may have to restart your computer to complete the repair.

  8. Update your QuickBooks to the latest release. This makes sure you have the most recent fixes and security update.

To give you the complete details on this process, please see this link: Repair your QuickBooks Desktop for Windows.


However, if the same thing happens after performing the instructions above, I suggest contacting our Customer Care Team. They'll be able to run a remote-viewing session that helps determine the root cause of this matter. 


I'm also sharing these links below to guide you in resolving issues if you're unable to connect to the server and on how to set up the email service properly in the system:

I got your back if you have any other questions or concerns. Just leave a reply below, and I'll get back to you. Take care!

Level 1

QB Desktop Pro 2019 locks up when I try to email an invoice

I am having the same issues. I have to kill QB in the task manager and restart several times. Once in a while it will send but generally only after several attempts and shut downs. This is pitiful!!!! I NEVER has an issue with my old QB. this 2020 Pro version sucks!

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