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Level 1

Email won't send invoices

QuickBooks Team

Email won't send invoices

Hi cydyetton,


You'll want to update QuickBooks Desktop to the latest release to successfully send invoices. But before we start, are you getting any error message? Moreover, you can follow the steps below to QuickBooks.

  1. Go to the Update to the Latest Release page.
  2. Make sure your product is selected. If not, click the Change link and select your QuickBooks product.
  3. Click the Update button to download the update file.
  4. Click Setup Automatic Updates to learn how to set QuickBooks to automatically download and install the latest updates.

Then, make sure to set up your email in QuickBooks Desktop.


For additional information, you can go over on this article: How to fix "Error: QuickBooks is unable to send your email to Outlook".


Here's an article for future reference about income and expenses in QuickBooks: Income And Expenses


Please let me know if you have any other concerns. I'll be right here to help.

Level 1

Email won't send invoices

Hello.  I use QuickBooks Desktop Pro 2018.  I prepared my monthly board invoices like always, went to File > Send Forms, confirmed that all invoices were selected, and hit Send Now.  The "Working" box came up that says "Sending emails to the recipients.", the status bar is about a fifth of the way through, and then nothing.  It never asks me for my aol password and never gives me an error message.  Nothing.  I let it "think" for about 35 minutes.  The only way to get out of it is to go into Task Manager and shut down QuickBooks.


I came onto this site and reviewed the suggestions, made sure all my updates were done (they were).  Made sure my settings were correct under Preferences.  Tried rebooting, shut down and restarting, anything I could think of.  Finally, I upgraded to QuickBooks Desktop Pro 2020, and guess what, it is still happening!   What else can I try?

Level 2

Email won't send invoices

Same here. I use QB 2020 desktop on Windows 10, 64 bit.


This isn't as simple as "updating to the latest version". This issue runs deep. Not only can I not email invoices...I can't email estimates....I can't print estimates or invoices...AND I can't save estimates or invoices as .pdf files.


This is a HUGE problem, as my business runs on this platform. This issue has been on Quickbooks' radar for over 6 months and STILL no resolution. What is the deal QB engineers?? We pay good money for this platform. Why is this problem not resolved after 6 months??  Does QB simply not care?

Level 2

Email won't send invoices

Update: I believe I found the solution to my issue. I have QB setup with my Microsoft Outlook, so that when I email estimates and invoices, QB sends them automatically to Outlook. I had used this method for years with great success. Then, one day, I signed up for a 2nd email account through the Microsoft Exchange online and ran that account through Outlook as well. So now I had 2 email accounts running to Outlook. Apparently, that's when the problems started between QB and Outlook.  I didn't realize it at the time, but once I removed the 2nd account from Outlook (Microsoft Exchange), everything between Quickbooks and Outlook started working fine again. Hope this helps someone out!

Level 1

Email won't send invoices

I am having an issue sending invoices. My issue is a bit different. The email comes up ready to go, but when I click send it doesn't respond. I can send emails fine through the default email client (mail) manually. I am running Quickbooks Desktop Point of Sale 19.0 Pro Level on 2 workstations. The software update utility says we are up to date.


Email won't send invoices

Hi there, spacetonemusic. Thanks for reaching out.


There are some possible reasons why you're unable to send an invoice via email. It could be due to the following:

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

To isolate the issue, let's ensure that your QuickBooks Point of Sale is updated to the latest release. Once done, check the web mail's settings in the preferences.


Here's how:

  1. Go to the Edit menu at the top. 
  2. Select Preferences
  3. In the left menu, click Send Forms
  4. Under My Preferences tab, select the email account you're using.
  5. Click Edit.
  6. Mark the SSL box, or just select Default.
  7. In the Server Name field, make sure the server name matches your email provider's settings.

For more details, check out below articles:

Keep me posted on how this goes on your end. I'll get back to you. Have a great day.

Level 1

Email won't send invoices

We are using Windows Mail Version 16005.13426.20566.0. We can manually send mail without issue. 

Level 1

Email won't send invoices

Similar problem. Using QB Pro2020 and AOL as my email client. I use to be able to email invoices from QB desktop using the option "web mail" under preferences and send forms option. I've been doing that for like 20 years. All of a sudden last week its not working. at first i was getting a pop up to keep trying my password which I know is correct. Now I get a pop up saying QB is unable to connect to my email server. Again, I did nothing. This started happening last week. Prior to that for a month or two I noticed when I went to email an invoice the window would pop up showing my filled in invoice template but it ALSO started showing a huge 1/2 page black pane on the right side of the page like QB was trying to open something else up. I thought it was something new in QB like it was trying to show a preview of the actual invoice but nothing ever materialized. I would click send and get the "email sent" confirmation and it worked. And the other weird thing is when I try to send an invoice which doesn't work there is a spastic spinning blue circle next to the cursor arrow that never stops until I close QB. I have a business associate who said he has the same problem. Is it something to do with AOL? Everything else works in AOL but QB.

QuickBooks Team

Email won't send invoices

Welcome ad thank you for posting here in QuickBooks Community, 

Skip123. I also appreciate you for providing detailed information about your concern.


To isolate the issue about emailing sales forms using webmail that doesn't work properly, I suggest resetting your QuickBooks release updates. Then, make sure it's installed successfully for critical fixes of your QuickBooks desktop and to clear all previous update downloads.


Here's how:


  1. From the Help menu, choose Update QuickBooks.
  2. Go to the Update Now tab.
  3. Put a checkmark beside Reset Update. Then, hit the Get Updates button.
  4. When the download finishes, restart QuickBooks.
  5. When prompted, accept the option to install the new release.




For additional information, you can click this article: Update QuickBooks Desktop to the latest release.


Once done, you can reset up webmail to ensure you get the most recent setup and to refresh it into its default status. Please follow the steps below.


  1. Go to QuickBooks Edit menu at the top. Then, choose Preferences.
  2. Select Send Forms and choose Web Mail. Then, Add.
  3. Fill out the Add Email Info and select OK.
  4. Hit OK to save your changes.


For additional details, you can click this article: Connect your email to QuickBooks Desktop.


Please refer to this article to see different troubleshooting steps on how you can fix the specific error you may encounter when using webmail in QuickBooks Desktop: Fix Error: Could not connect to the email server.


If you have further questions, just let me know by leaving a comment below. I'm always glad to help. Have a good day.

Level 1

Email won't send invoices

None of you suggestions work.  Do you have a real fix yet?  It's tax season...I really don't have the time to waste with canned responses and fixes that don't work.  I need to be able to invoice a good majority of my clients via email and can't.  Please advise.

QuickBooks Team

Email won't send invoices

Hi theodorako, 


I do appreciate your time in performing the steps to get your customer invoices to be sent. I'd suggest reaching out to our Phone Support Team so they can investigate this issue further. They have the tools to remotely look into your settings. 


You can check out these links that can also look into your email preferences:


The Community is around to help you if you need more help. Take care and have a great day!

Level 1

Email won't send invoices

I too use AOL to send email and I am having the same issues with it having me re-enter my password. I have tried all the normal fixes that you guys have recommended on here. Is there anything else to get this problem resolved???

Kristine Mae
QuickBooks Team

Email won't send invoices

I'm here to help you, Chicagolandfleet. Let me share a few steps to fix it.


First, let's check your email settings. You'll have to open your online email service and review the settings and preferences. There might be features that are blocking our program to connect.


Then, we'll have to check the antivirus settings. It may be blocking the connection as well. You'll have to search for your antivirus provider's website for the steps to allow port exceptions. 


If it didn't make any difference, let's try to use and connect a different email.


Get back to us if you need more help with this. We'll reply as soon as we can. Take care!

Level 2

Email won't send invoices

I had an issue with QB and Outlook communicating recently. It wouldn't send invoices, so I'd have to save them as .pdf files and email them directly. The problem ended up being that I had started a new email account with Microsoft 365 and had joined it with my original Outlook account. Once I closed the 365 account down, everything started working properly again. I also would randomly have issues sending emails/invoices if I had my VPN running. Not always but sometimes. Once I would disconnect from the VPN, then they would go out. I hope this helps someone out there that can't get a real answer from the support team. Best of luck!

Level 1

Email won't send invoices

My quickbooks has been set up to send invoices by email for years.  I updated my Quickbooks 2020 and now it says my password is wrong.  I do not have time for this.

QuickBooks Team

Email won't send invoices

Let's get this sorted, @DA37.


I got few steps to help you fix the incorrect password error when sending emails in QuickBooks. To start, let's update your QuickBooks program to the latest release. This is to make sure that you have the updated components. 


Next, check your email settings to determine it does not block QuickBooks. This method varies depending on your email service. Follow Step 2 of this article: Fix webmail password issues in QuickBooks Desktop.


Once done, check your antivirus software this may accidentally block the connection. To do so, search for your antivirus provider's website for steps to allow port exceptions. 


For more details, visit this link: Fix webmail password issues in QuickBooks Desktop.


When everything is set, email the invoice again.


You can also customize your email templates to make them more personalized when sent to your customers. For the detailed steps, check out this article: Create custom email templates in QuickBooks Desktop. 


Don't hesitate to post again here if you have further concerns sending emails in QuickBooks. I'm just a post away to help. Take care always.

Level 1

Email won't send invoices

I have a Aol account, but wants me to update a gmail or yahoo?

QuickBooks Team

Email won't send invoices

​​​​​​Hello, @kprelect.


I have an idea of why this may not be working for you.  Newer versions of QuickBooks can use secure webmail.  QuickBooks versions that work with secure webmail like AOL, include QuickBooks 2019, and 2020.  It is possible your QuickBooks is not a new enough version to support this domain. 


You may find this article helpful: Connect your email to QuickBooks Desktop.

  • Are you able to provide screenshots of the messages you are seeing?
  • Can you also provide a screenshot of the version of QuickBooks you are currently using? (you can find this information by pressing F2 within QuickBooks).

I look forward to hearing from you and getting this worked out! 

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