Not only am I having an issue when trying to email an invoice, but all reports are now causing my outlook to freeze and not respond.  Having to shut down and try again with no success.  Very weird because I have three computers running the exact same window, Microsoft, and quick books.  Everything was ok for a long time until a little over two months ago one computer had this issue and then just this morning a second computer has this issue.  Just waiting for the third one to cease up and I will be out of business.  I have talked to support and they tried for about two hours on the phone when the first computer had the problem and this morning when the second had it as well 2 QuickBooks support individuals told me to sign up and pay for a service plan and when QuickBooks figures out the problem they will fix it.  Not real sure when that will be, but at least they have more of my money.

I"ve been having this issue with two users for the past year or so. Haven't been able to fix it.

So far, I’ve tried the following:

• Running the QuickBooks repair hub (Print & PDF Repair tool, program diagnostic tool, and quick fix my program). Sometimes it will work for a few hours but the next day the issue occurs again.
• Running Outlook in online mode. Doesn’t work at all. Needs to be in cached mode
• New Outlook profile
• Temporarily gave her local admin rights
• Full MS Office repair
• Full QB Ent 2020 repair
• Full removal and reinstall of QB including deleting the corresponding appdata folders
• Logging in as a different QB user, even QB admin
• Making sure .NET 3.5 and .NET 4.0 are installed and comparing the versions to workstations where it’s functioning.
• QB Tools Hub repair option. This works but only for an hour or two.

What’s odd is that some of the fixes above seem to work temporarily but the next day or even a few hours later,  it happens again. A lot of out clients use Quickbooks but I've only had this issue happen for two users so far. 

Hi there, paul83.

Welcome back to the QuickBooks Community. I appreciate you for performing some steps to resolve the issue of being unable to send your emails via Outlook. I'll ensure to share an update about the problem and route you to the right person to assist you further on this so you can get back on track.

The issue about Outlook crashing when sending invoices emails is currently tagged as an ongoing issue. Our Product engineers are now working to resolve this as soon as possible.

For now, you can try running both QuickBooks and MS Outlook as admin as a workaround.

Here's how:

1. Close QuickBooks Desktop. Then, open the Windows Start menu.

3. Type "QuickBooks" into the search. Then right-click the QuickBooks icon and select Open file location.

4. In the folder, right-click the QuickBooks.exe file and select Properties.

5. Choose the Compatibility tab. Then, select to check the Run this program as Administrator option. 

7. Click Apply and then OK.

Then, I also recommend contacting our QuickBooks Desktop Support Team, so they can add you to our notification list. This will help our engineers determine the number of affected users. You'll also receive an update through email once this has been resolved.

Lastly, you may refer to this article to view possible reasons why Outlook is missing as one of your options and how to fix this: Fix Outlook is missing in send forms preferences.

Please let me know if you have any other questions while sending emails from QuickBooks. I'll be right here to help, paul83. Have a good one!

Hello,

I am having the same recurring issue of being unable to email invoices through quickbooks. I would appreciate any help. I am running Edition Windows 10 Home
Version 21H2
Installed on ‎4/‎6/‎2021
OS build [removed]
Experience Windows Feature Experience Pack 120.2212.4180.0

I have tried unselecting and reselecting Microsoft XPS document writer, with no improvement.
 

Thanks for reaching out to us on this thread, @njdavis7. I appreciate you for sharing the steps you've done before contacting us. 

To make sure I'm giving you the right fix, I want to know if you receive any error messages when emailing your invoices.

In the meantime, I recommend updating QuickBooks to the latest release. Here's how: 

1. Go to the Help menu at the top right, then select Update QuickBooks Desktop on the drop-down.
2. On the Options tab, click Mark All, then Save.
3. Now, go to the Update Now tab and mark the Reset Update box, then select Get Updates.

After that, check the web mail’s settings in the Preferences section. Here’s how:

1. Go to the Edit menu and choose Preferences.
2. Click Send Forms., then choose Outlook under My Preferences tab.
3. Click Edit.
4. Mark the SSL box or set it to Default.
5. In the Server Name field, make sure the name matches with what’s on your email provider’s settings.

That should get you back on track. You can also save these artcles for your reference: 

• Set up an email service.
• Error: Could not connect to the email server.

Let me know how this goes and if you need anything else. I’ll be on the lookout for your response. Take care!

Your level one techs overseas put you through hour long calls before they tell you that its a known issue. Really? They wanted me to verify my data...to send emails with Outlook? One told me to change all the company emails to something else and it would work...really? By the time I call, I've done 85% of what they ask me to do and they want me to do it again? I have Windows 11. I've been using QuickBooks Pro Plus 2022 with Outlook since we purchased the PC over a year ago and it worked flawlessly, but today we can't send Outlook emails. REALLY SAD!!!

We have been having this problem for over a year, it all started when we ran the upgrade to Enterprise Solutions 22.0, we tried many of the solutions listed in this thread nothing worked. Our computers are on Windows 10 and use Outlook 2013 desktop version.   We finally gave up and have been spending our time printing all the estimates and invoices to pdf and then having to manually attach the files to our e-mails in outlook.  I can only imagine how many hours we have now wasted.  So when we recently upgraded to Enterprise solutions 23.0 we were hopeful that the problem was fixed.   And it was, well for about 2 weeks and then last nights update broke it again.   I find it hard to believe that a software company that charges quite a bit of money every month for their software cants seem to fix this problem after more than a year.

We were thrilled that when the e-mail feature started to work again that we could now send our invoices out from QuickBooks with the on-line bill pay feature enabled.  Sadly now that we cant e-mail invoices from QuickBooks once again we will now have to field countless complaints from our clients that we don't offer online bill paying.

Please QuickBooks and intuit get your act together and fix this basic problem!

If there is a permanent solution please post again.

Thanks.

UPDATE "EVERYTHING"

I too fought email problems for years. I had to use a lot of work arounds to limp by. I tried everything. Recently I discovered a suggestion to update my email program. Since I use Office 365, I understood it stayed up to date. I was able to update it and Quickbooks finally worked. I also updated Windows and somewhere along the line I updated Quickbooks. It didn't work and caused all my problems to change requiring different work arounds. Don't update Quickbooks unless you try EVERYTHING else first! I WILL NEVER UPDATE QUICKBOOKS AGAIN. I agree with you, updates always cause problems with no fixes, an unstable program and crashes. I wholeheartedly agree, INTUIT SHOULD DO BETTER.

I recommend buying the desktop version. It's YOURS (3 years supported), you can use on multiple computers for multiple businesses (multi user licenses are necessary to share a file in real time) and the data is YOURS when you stop using Quickbooks.

GOOD LUCK!!

Hello there, eivc1.

I recognize how vital for your company to get the email feature functioning back to normal. It lets you automatically send transactions and save time. Let's configure your email service and set up Outlook to work with QuickBooks Desktop (QBDT). I'm here to help and guide you through the steps. 

Before we start, make sure you’re using Outlook 2010 or newer and have an Outlook email profile. Then, reach out to your internet or email provider and gather the following information:

• Username
• Password
• Incoming email server address
• Incoming email server type
• Outgoing email server address

Next, head to the Preferences menu and set up Outlook. Here's how:

1. In your company file, go to the Edit menu at the top bar and select Preferences.
2. Navigate to the Send Forms menu on the left panel and choose Outlook and OK.

Here's an article that goes into detail about the process: Connect your email to QuickBooks Desktop. 

In addition, the following links contain topics that will help you manage sales-related tasks as well as solutions on how to troubleshoot email issues:

• QuickBooks is unable to send your email to Outlook
• Sales and customers 

Feel free to visit the Community if you still encounter the same issue or have additional QuickBooks concerns. I'll get back to help you the best that I can.

I have done all that including upgrading to Enterprise 21.  I have also changed my Quickbooks profile.  I have used the QB tool hub.  Nothing fixes the problem.  Using the Email Invoice function eventually crashes Quickbooks.

All the QuickBooks troubleshooting that the QB techs are posting are for people who don't know how to setup their email to work with QuickBooks, be either desktop, Pro, Pro Plus, etc. I spent over a month with many QB techs and non could fix the issue. After hours on the phone, they would come back and say it was a known issue. Well, it WAS a known issue and has been a problem since 2017 if you Google the errors you are getting and see what people are posting. We have QB Pro Plus on a subscription and it worked fine until a couple of months ago and then the error messages started coming up. We did notice that if you have a lot of invoices or estimates that are in the queue, but haven't been sent by email, you will get the Out of Memory error. However, sending emails plagued us and we too, had to work around.

As of Thursday, 03/16/2023, we had a very large Windows 10 update. Took 3 hours. Followed by a large QuickBooks update. We even had to uninstall and reinstall our HP software. When all these were completed, our QuickBooks is sending via email again. If you have not updated your Windows 10 and QuickBooks ( or just QuickBooks on Windows 11 ), then I suggest you try. It resolved our issue. You will not get a resolution through QuickBooks, level 1 techs.

Thanks for swinging by the Community, Tony.

Allow me to point you in the right direction to prevent QuickBooks Desktop (QBDT) from crashing when emailing invoices to customers.

I admire you for performing the shared steps above to resolve your concern about being unable to send invoices via Outlook. Getting back and forth isn't easy. Thus, it's best to reach out to our customer support for further assistance. They have access to a screen-sharing tool that will determine the root cause of the issue and may raise an investigation if need be. 

Furthermore, there are a few ways you can take and process payments in QBDT. You may either turn on online payments for the invoices you email to customers or process them in person.

You can always get back to us if you have more questions about emailing invoices. We're always here to assist you further. 

Hello, this same issue is being observed with Intuit Profile connecting to Outlook.   It freezes, i can unfreeze it by closing the opened Outlook.exe file in task manager.  Then i get a return  "Error Sending Mail (2)" message.  

Can someone at Intuit please update your software ?   this issues is resolvable by finding out what Microsoft had done to Outlook. 

Hello, this same issue is being observed with Intuit Profile connecting to Outlook.   It freezes, i can unfreeze it by closing the opened Outlook.exe file in task manager.  Then i get a return  "Error Sending Mail (2)" message.  

Can someone at Intuit please update your software ?   

this issues is resolvable by finding out what Microsoft had done to Outlook. 

I appreciate you joining the conversation and sharing your experience about the issue, @MarioH.

Have you tried performing some troubleshooting steps to rectify the error? If not, I can give you some tips on what to do when you're unable to send emails.

Step 1: Edit your admin privileges  

Step 2: Edit your email preferences in QuickBooks 

Step 3: Check your Internet Explorer email preferences   

Step 4: Repair your MAPI32.dll   

Step 5: Install QuickBooks again

Here's an article that details the process: How to fix "Error: QuickBooks is unable to send your email to Outlook"

However, if you're done doing these steps, I recommend reaching out to our QuickBooks Support team. Our phone agents can further investigate this issue.

Here's how to get in touch with us:
 

1. Open QuickBooks.
2. Go to Help, then select QuickBooks Desktop Help/Contact Us.
3. Select Contact Us.
4. Give a brief description of your issue, then select Continue.
5. Select to chat with us or Have us call you.

Please consider checking our available hours so we can address your concern on time.

In the meantime, you can check this article for additional information about managing your QuickBooks account: Help articles.

The Community is always around to assist if you have further questions. We'd be glad to help. Keep safe.

Have done that multiple times, most of the reps I have delt with are not aware of how wide spread this issue is and have no idea what has already been and failed to resolve the issue.  It's like starting over from the beginning each time.  Once in a while you do get to someone who has seen this and the answer always is, they are aware and are working towards a resolution, be on the look out for an update.  And the years keep rolling by with nothing resolved

I have the exact same issue, spent over 4 hours trying to resolve it.  I have a temporary work-around by using an older version of Outlook 365 or others from 2021.   Intuit Profile and Quickbooks simply dont care to resolve the issues from a programming issues. Tax season is busy and they left me in the dusty basically.  

Try Down-Grading your Outlook Desktop Version or use another Email Software program.  I also noticed that by changing the default email away from a Microsoft Exchange in outlook also helped.  

I first came across this issue 3 years ago, and this thread started in March of 2020. I believe there are other threads on this same topic. As much as I understand you are attempting to be helpful by posting standard basic troubleshooting and referring users to your helpdesk, its a bit tone deaf. 

I think you fail to recognize the level of frustration around this issue and the lack of trust we have, the helpdesk is really forwarding the messages to upper management. Please provide a genuine method of expressing ourselves to management on the severity of this situation.

Not sure if this will help anyone, but i switched to the web email and make sure you use "modern authentication" when entering your o365 creds.  Then it seems to make a connector in the background and doesn't open Outlook at all, rather you get a window with your QB stuff in a QB window. 

Doesn't fix the issue, but seems to at least work.... for now

Fix that works for me until QB gets their heads out of the butt and fixes this:

Issue; If I send an email from QB and just hit the Send button, everything is fine. But.. if I change ANYTHING about the email, such as the recipients address, the moment I try to edit the email Outlook freezes until it eventually crashes.

Solution that works:

As soon as QB creates the email, Save the email as a draft and close it.

QB will release the window and think it's been sent.

Go into your drafts folder, open the email, and edit it like normal and send.

It's a pain to have to do this every time but it works for me until QB resolves this.

• After QB requested an update, We can't email our invoices to customers. If we had this problem before, we'd shut down the entire computer and reboot. Usually this worked to fix the email problem.  It does not eork after the UPDATE.  I have been printing the invoices and sending it using my printer, which copies, prints, scans to email . This us the only way I can get my clients their paid invoices.  Counter-productive time wise. 

Hi there, Char20.

Can you tell us what happens when you email your invoices? Are you getting an error message? 

We're asking these questions to make sure that we are giving you the right steps and information and steps to sort this out.

Please reply back to us to share more details. We look forward to it. 

I'll chime in here as I've seen this issue for 4 years, and Intuit has done ZERO that I can tell to fix this issue. They quickly blame Microsoft updates but fail to point out that their code is fragile. Case in point, you only need to look in add/remove programs to see that they load 5 versions of Microsoft Visual C++ Redistributable, dating back to 2008! 

What is Visual C++ Redistributable? It's a package that installs run-time components of Visual C++ libraries. These components are required to run C++ applications developed using Visual Studio and link dynamically to Visual C++ libraries. In short, one possible reason 5 versions are installed is that Intuit is attempting to support a significant amount of legacy code dependent on outdated and/or no longer maintained software libraries built by Intuit or another third party. The dependency on legacy libraries, whether specific to C++ or other development frameworks used by Inuit can create any number of negative user experiences...this email issue may just be one.

My company has over 18 years of experience as a QuickBooks Enterprise customer, we are currently on Version 23 (latest release), on a high performance server, with 10 users working from PCs that far exceed the recommended requirements, and we still see this issue off and-on, and each time the fix...or at least the supposed fix...is different. We have never been able to tie our issues to any MS updates; however, its always a possibility.

Lastly, current generation applications should not need to have repair tool run weekly! Intuit simply needs to do better! The support techs are not the issue, they can only work with what script leadership provides them. This is software engineering issue!

The QB Pro Plus 2023 desktop support could never fix the issue, nor could the Level 3 support with the Office of the President. However, the Level 3 tech did try hard and spent over 8 hours on the issue. Contacting Microsoft was a complete waist of time. Their techs had no clue what to do. Our problem is on a Windows 11 desktop PC that uses Outlook 365. I discovered a work around that works for us in the meantime, but has its drawbacks. We are able to create invoices and estimates in QB Pro Plus, but Outlook must be closed. When the invoice or estimate is completed, we can still open an Outlook email window and apply attachments. When ready, we press SEND, but the email goes away and does not send out. At the end of the ship, the invoice clerk opens Outlook and all the invoices and estimates created during the shift are sent out at the same time. This resolves sending invoices within QB Pro Plus, but it eliminates the clerk from receiving emails throughout the shift. Now, the clerk opens Outlook at the beginning of the shift every day, reads the emails, then closes to work on invoices. As advanced as Microsoft and Quickbooks are, they still cannot figure out this issue. We could go back to Windows 10 and the problem would be resolved, except that Windows 10 versions are slowly moving toward not being supported by Microsoft. It is a plus that I have a lot of IT experience, but frustrating that I know more about it than QB or Microsoft.