Showing results for 
Search instead for 
Did you mean: 
Level 2

Anyone solve emailing invoices/estimates problem?

I've read other threads online about this issue, but I haven't seen a solution. I use QB 2020 desktop on Windows 10, 64 bit. I also use Microsoft Outlook 2016 as an email client. I've used this combo successfully for quite a while. About a month ago, QB started acting up, not wanting to send emails. i could do a work around by hitting 'ctrl/alt/delete' and shut down Outlook b/c it was freezing when trying to communicate with QB (don't know if Outlook or QB was the issue). Anyhow, after that I'd try to send the invoice/estimate again, and everything would go smoothly. One day, however, QB started freezing when I would click on 'send, estimate' or 'send, invoice'. It just froze and didn't bring up an error message or anything...just a blue circle frozen in time. The only way out is to 'ctrl/alt/delete' and shut QB down in the task manager. I also found out the QB will freeze up when trying to save the estimates and invoices as .pdf files... And also won't print estimates or invoices. It appears that something related to the .pdf creation in QB is at fault. So that's the issue - I've seen it posted online - I have seen no resolution. So if you have gotten through this, please let me know how, it would be MUCH appreciated. My entire business runs on sending estimates/invoices, and right now QB is of virtually no help. All I'm seeing is to add your name to a ticket, which won't really matter, because if they (the engineers) create a fix, it will be in the update which happens automatically. Thank you

4 Comments 4
QuickBooks Team

Anyone solve emailing invoices/estimates problem?

Hello there, @gp28.


I've checked our records here if there's an ongoing issue about this, but I haven't found any.


There are a few possible reasons why this is happening:

  • The email preference being set incorrectly.
  • A damaged QuickBooks installation.
  • The domain admin was blocked.
  • Account security settings from your email provider.

First, we want to make sure your QuickBooks Desktop software is in its latest release. QuickBooks periodically provides maintenance release and software updates. This can fix emailing issues, add features or enhancements, and update compliance information.


You can download the release patch from the internet, by following the steps below:

  1. Click this link Downloads & Updates.
  2. Add your location from the Select Country drop-down.
  3. On the Select Product drop-down, choose your QuickBooks Edition.
  4. Choose the version year of your product from the Select Version drop-down.
  5. Select the Search button.
  6. In the Here’s your product section, click the Get the latest updates link.
  7. Select Save/Save File to download the update.
  8. Once downloaded, double-click the file to install the update.

Second, check the settings in the webmail preferences:

  1. At the top menu bar, click Edit then Preferences.
  2. Click Send Forms on the left panel.
  3. Under My Preferences tab, select the email account you're using, then click Edit.
  4. Mark the SSL box, or just select Default.
  5. In the Server Name field, make sure the server name matches your email provider's settings. If it shows for example, change the name and click OK.
  6. If you see a Use enhanced security box, ensure it has a check on it.

If you're getting an incorrect password error message, please follow the detailed steps in this link: QuickBooks Will Not Accept my WebMail Password.


After that, create a test invoice and resend it to your email to double-check. If the issue persists, check out these articles for further guidance:

If all else fail, I recommend contacting one of our Technical Support Team. They have the tools to check your company file and help you send invoices without issues. Here's how:

  1. Go to the Help menu.
  2. Click QuickBooks Desktop Help or press F1 on your keyboard.
  3. At the bottom, click Contact Us.
  4. From the Dialogue box, enter your question.
  5. Click Continue, then select Get a callback.
  6. Enter the information needed.
  7. Once done, click Confirm my call.

To ensure that you'll be assisted on time, check out our support hours.


If you have any other QuickBooks concerns in the future, you can also read our help articles: Help articles for QuickBooks Desktop.


Keep posted if you have any other questions about emailing transactions from QBDT. I'm always here to help you out.

Level 2

Anyone solve emailing invoices/estimates problem?


Thanks for the reply, but it appears you didn't read the entire post.  Your solution is strictly about sending invoices/emails. The problem is much deeper than that. And there IS an issue going on; I've read several posts about it. No settings in QB were changed to initiate this problem, so the settings are fine. Updating will NOT fix this. Sounds like technical support may be the answer, but I posted to the community hoping that an individual not related to QB would respond with a legit response. 

Level 1

Anyone solve emailing invoices/estimates problem?

I have run into this problem over the years and failed to resolve it. I did one time though, and promptly forgot how I did it. I have however found a way that resolved it at least for today. In reading the response from QB, I decided to test out a theory. I went to my GOOGLE account settings (I use gmail) and then security. You have to turn on "Allow less secure apps" Google doesn't like this and will send you numerous emails saying someone may be hacking  your account. Why they consider quickbooks to be a less secure app is beyond me. But once I clicked that TURN ON feature, my QB sent emails again. This time, I saved the instructions in a note on my phone so I can remember it!

Level 1

Anyone solve emailing invoices/estimates problem?

I am a LONG time Quickbooks user, using the very first edition in the late 90s. I have overcome many obstacles over the years using QuickBooks tools, rebuilding company files, or restoring from a backup.  I created an Invoice and attempted to save it as a pdf. POOF! The application is locked up.  Not responding at all.  I use task manager to close the app, now when I try to open the file, I get a familiar pop-up warning about recording a transaction that is over 30 days in the future.. ??? Not sure what the warning is concerning because if I chose Yes or No, the app completely freezes up again, and I never get the opportunity to open the Invoice that I desperately need to save and send. I have used every tool available to repair my company file, and every one completes with no errors detected. I restore the company file from one of the 3 recent backups and it does the exact same thing again. So, I find a much older company file and it repeats the same issue.


I just restored an old back-up so I can try printing the Invoice and I get more really odd issues, when I print, it attempts to print over 4500 pages I stopped my printer from printing all of these apparently duplicate Invoices but they are formatted all wrong in the center of the page like it is printing a 4" x 6" label, when I cancel the printing the app locks up once again. Each time the app locks up the new restored company file is corrupt and locks up before I can try anything else, so I must restore a back-up and try something else. 


I cant explain how frustrating this is.


This is now my only solution before re-installing the QB program. I did a screen shot of the Invoice so I can e-mail it to my customer. (not professional)


the only thing I have yet to try is re-installing the entire program. I just want this to go on record as a Major issue. 


I am using Windows 11 64bit Quickbooks desktop

Need to get in touch?

Contact us