I saw the comment about virus scanner blocking.  This cannot be the case in this virtual machine remote desktop session - there is not virus scanner installed at the moment.  We found a workaroudn to use "Print" vs "Save as PDF" and this is sufficient for now.  

remove the logo from the invoice template see what happens fixed mine.

After days of frustration.

Wow.

Mel

remove the logo from you invoice template.

remove the logo from your invoice template.

Mel

remove the logo from you invoice template

remove the logo from the invoice template.

I am a ProAdvisor and have discovered a workaround for this problem. I have also reported the solution to QB under INV-0671.

We are operating Windows 10 with 2019 QuickBooks Enterprise with the Manufacturing module installed with multiple users. The problem typically appears when a user turns on or restarts the PC, which resets the startup files.

When QB "freezes" while sending an Invoice or Estimate, do not CTRL-ALT-Delete. This can damage the database requiring a Verify/Rebuild Data. Instead, open Widows Task Manager, select QuickBooksMessaging and End Task. (NOTE: be careful not to end any other programs as this may require the PC to be restarted.) This action will release QB to continue as before. QB will automatically reopen QuickBooksMessaging. Next, when you attempt to send the email again, the New Email window should appear in Outlook. 

As background information, QuickBooksMessaging is used to communicate with other users, connects to outside applications and monitors who is logged onto the database in multi-user applications. When logging on to QB and you receive a message that the user is already logged on, this is the culprit, due to an improper shutdown. Follow the same procedure above to resolve and logon.

Quickbooks froze every time i tried to send an email or invoice. I had this problem for months across multiple versions of QuickBooks and outlook. was told it was xps document writer and temp files and all that. if you run into this try changing the template you use for invoices. Worked for me...goodluck

Thank you for this workaround but do we have a RESOLUTION to this issue yet? It's been months and I know that with COVID, everything is sort of behind but this has been ongoing for my client since January!

I've never received a phone call from QB support even though I've added myself and a couple of my technicians to this ticket multiple times and there is nothing online. 

Wanted to reply to this issue with a more current update.  I was also dealing with my QB crashing when trying to send an invoice (as of April 2021).  I tried all of the suggested fixes posted in all of the forums, including being on call with QB Customer Support for hours.  Someone posted in this forum that they created an invoice with a different template and then they were able to send their invoices.  This was the solution that worked for me.  I created a new basic invoice, without our logo, and was able to send an invoice with no issues.  

Exact same issue happened to me. Quickbooks 2020 desktop. I use gmail in quickbooks. The so call work around  doesnt work. How do I reach the support team. Its not via these useless forums, is it? This software should be sold with the customer service number in bold on the package. I just got my bankfeeds to work yesterday now it will not send an email. I have read enough forums to create a liberal arts program and they have been just as useful as one. This is the  money that keeps my family and business and I regret my purchase deeply.

Good day, Amasloan!

Let me help you in fixing the email issue you encountered.

First, make sure you're using the latest release of QuickBooks Desktop. Then, send a test transaction to yourself. 

If the same thing happens, please check your email settings. There could be some settings and filter preferences that block your emails from QuickBooks Desktop. Make sure to enable access for less secure apps and set access preferences for specific apps like QuickBooks.

Lastly, check your antivirus settings because antivirus software can block connections. Don't forget to email yourself a test transaction every after troubleshoot to check if there's a difference.

Also, I encourage you to reach out to our Support Team if this behavior persists for further investigation. You can follow these steps:

1. Go to Help, then select QuickBooks Desktop Help.
2. Select Contact Us.
3. Enter "Send invoice email", select Let's talk and then choose a way to connect.

For more tips and references in handling the company's income and customers, visit this page: Sales and customers.

I'm looking forward to assisting you again. Take care!

This issue isn't constantly reoccurring but happens enough to frustrate my team when it does happen. When they try to email invoices, outlook says its not responding and then restarts. Sometimes QuickBooks itself will freeze and force shuts down QuickBooks.

Every time it happens before the shut down it ask if I want to send a report and each time I take the time to send the report with a contact email.

Ironically I am an IT Professional and support many clients QuickBooks programs and I feel after several years I am a bit of an expert. SO WHAT GOOD DOES SENDING MULTIPLE REPORTS WITH EXACT DETAILS OF THE CRASH?!?!?!?!

Hello, 

This is start happening on a few computer on my company. I was able to resolve by uninstalling Office 365 32 bits version and replacing it with the 64 bits version. 

Two computers with the issues (windows 11, QB Enterprise version 22), at least 2 out 2 the issue was resolved.  

Using QB Pro 2020, but not on a daily basis.  Sent invoices via "send forms" sucessfuly about a month ago without issue. I got a QB update and launched it (required restart). I cannot "send forms" as it locks up and must use task mgr to end QB!  Multiple trys to go to "preferences, send forms" and immediate freeze. Utilized file repair to check company file.

Using Microsoft 10, all current updates, no other issues with mail server (outlook) or any other app, Performed system maintenance, performance, and functioning properly. Sought help with QB Support. On phone +3 1/2 hrs trying this + that, everything I had done so far in QB plus, remove & reinstall QB Pro 2020, QB Patches, checked versions, to no avail! very frustrated as business is stalled for a week trying to resolve this issue. Everything points to corruption in QB as PC server has no issues. Told by QB Support that they escallated to Tech Support, but not calling back! Told I need to buy expensive annual service to repair QB problem. UGH!

ADDENDUM: I found that this crash/freeze also happens in "customer center", choosing a customer and clicking the hyperlink for their email. Message comes up that "your email is not compatable...". Only way out is to end QB app via task manager.  We use Outlook (microsoftonline) in browser, not desktop app.  Secondary call to QB Support, got me to Tech Support. Confirmed issue was QB based, not my hardware, OS, antivirus, or outlook. Confirmed two issues ongoing, since summer of 2021:

INV - 0671 and INV - 45586. Cannot confirm how those two investigations overlap.  Also talked to Merchant Services about a method to incorporate a hyperlink for payment in an out-of-QB email.  NO CAN DO. Only method is outside ACH to your bank or take CC info from customer and enter in QB "merchant services".

It doesn't seem you are working very hard because it has been more than 2 years since THIS post. Customer service could not be worse. It is virtually impossible to contact a PERSON. When you do, they seem to have no ability to help.

I can not email from quickbooks 2021 desktop. It crashes the program every time. I have run every File Doctor and QB Tool Hub utility. Nothing helps. Fix your program or I will not purchase again.

I don't believe QB is interested in fixing any problems. These problems have been going on for YEARS with no solutions. I have never found an answer/solution to any issue.

yes it is still present in 2022. No fixes are ever found.

Yes, this is happening to me as well.  It has gotten worse and worse over the last few weeks.  I'm using QuickBooks 2022 Pro Plus, and Windows 11.  It is now at the point that it crashes at EVERY instance when I send an email (used to be sometimes it would work, sometimes it would crash).  It is so frustrating.

Hi, @mnalaboff.

This isn't the kind of experience I want to you have when sending invoice emails from QuickBooks Desktop (QBDT). I want you to know that our engineers are already looking for a fix so you can send emails to Outlook seamlessly. The investigation (INV-0671) is still open and in progress, if you haven't yet, I recommend reaching out to our Support Team to add your name to the list of affected users. Once added, you'll automatically receive an email notification of the recent updates.

Additionally, you can update QuickBooks manually or automatically to get the latest features and fixes.

For now, you may set up and temporarily use webmail in sending your emails through QuickBooks.

Here's how:

1. Go to the QuickBooks Edit menu and click Preferences.
2. Click Send Forms.
3. Under the My Preferences section, select WebMail.
4. Enter your email address and select your provider from the Email Provider drop-down.
5. Select the Use Enhanced Security checkbox and select OK.
6. When prompted, sign in to your Intuit account.

You can also check out this article for more information: Connect your email to QuickBooks Desktop.

Please let me know if you have any other questions while sending emails from QuickBooks. I'll be right here to help. Have a good one!

Hi Angelyn,

Thank you for your recommendations and suggestions.  I'm unable to add my name to the INV_0761 using the link you provided, because I don't have the correct Enterprise CEO account required.  Can you help with that?  I have tried all your suggestions, and just uninstalled QB and reinstalled it, and it crashed again on three attempts (crashed on all 3).  It even crashed when I was attempting to review my company preferences to make sure they match your recommendation.  This is beyond frustrating.  I'm hoping for a fix, because of right now, I'm having to save each invoice or payment receipt as a pdf., and then attach it to an email.  

-mnalaboff

Thanks for coming back for more support, @mnalaboff. I'll be your QuickBooks guide today.

I'd want to help ensure your company is added to the lists of affected users.

Since the issue persists, and you're unable to add your account on the link, I'd recommend contacting our Customer Care team. They can take all your information and manually add you to the list. 

For future reference, you can visit our QuickBooks Articles hub to search for ideas related to any of your concerns.

I'm always around here to be your guide if you have any additional or other concerns. Take care!

This has been happening for YEARS!  And we keep getting the same response, we are working on it.  The only work around I know is same the file to your desktop and manually attach it to your outlook email.

Sorry I could not be more help but obviously this one has their "Engineers" stumped

Tony