Quickbooks is unable to send emails due to a network connection failure HELP

Thanks for sharing detailed information about your concern, @WillShimar. I look into this and found an investigation and I'm here to help your route to the support team.

Currently, we have an open investigation about QuickBooks being unable to send emails due to network connection failure when sending batch emails using a Gmail account. Please know that our product engineers actively working to know the root cause of this issue.

I know you already contact us but, I'd recommend getting in touch with our Customer Care Team again so that you'll be added to our notification list. Rest assured, you'll receive an email notification once we get this sorted out.

Before diving in, I encourage checking our support hours first to ensure that we address your concerns time. Here's how to connect with us:

1. Open QuickBooks.
2. Go to Help, then select QuickBooks Desktop Help.
3. Click Contact Us.
4. Enter your concern, then select Continue.
5. Sign in to your Intuit account and select Continue and then Continue with my account.
6. We'll email you a single-use code. Enter your code and select Continue.
7. Select to chat with us or Have us call you.
8. Have our representative link your case to this investigation number for faster transaction: INV-88439.

For now, send the invoices of three or fewer and use a different webmail provider like Yahoo or outlook.com. You may also use another method like Outlook or QuickBooks Email service if available. For more details, about connecting your email, see this article: Connect your email to QuickBooks Desktop.

I'll be sharing these resources that will help you track your customer's transactions and personalize your templates in QuickBooks Desktop:

• Get started with customer transaction workflows in QuickBooks Desktop
• Use and customize form templates

We appreciate your patience. Don't hesitate to leave a comment below if you have any additional questions about sending invoices. I want to make sure everything is taken care of for you. I'll be here to help. 

We too have this problem and have upgraded to Enterprise 2023 as well. It does seem intermittent on the network error and hope to hear an update from QB engineers soon. 

I am unable to email any invoices, it doesn't matter if it is a gmail account.

this is the answer i received:

Thank you for contacting Intuit. We are aware that some customers are encountering issues sending mail from QuickBooks Desktop through G-Mail. We are actively working to resolve the issue. We apologize for any inconvenience. If you have a non-G-Mail email account for you business you may use that instead.

We have been having the same issue since yesterday and have found a workaround that works for us. It's fairly simple, so worth at least trying out.

One big caveat: this only works if you use Gmail, but have a custom domain that you use through Gmail. In other words, if your email ends in @gmail.com, this won't work. If you use Gmail, but your email address is @yourdomain.com, it will work.

Basically, we reverted to using the old, less advanced way of connecting to Gmail.

• Go to Edit, Preferences, Send Forms.
• Delete your email account.
• Add a new email account.
• Enter your email address as the "Email ID"
• For Email provider, DO NOT select Gmail. Instead choose "Others"
• Servername: smtp.gmail.com
• Port: 587
• Check the SSL/TLS box
• Click Okay.

For this to work, you will also need to create an "App Password" for quickbooks in your gmail account. Instructions to do that are here: https://support.google.com/mail/answer/185833?hl=en

Your "App Password" will only be for use when email from Quickbooks and is different than the password you use to log into Gmail.

The next time you try to email from QB, it will prompt you for your email password. When it does, use the "App Password" we just created.

Same here in Desktop 21 Pro. It worked last month when I sent out statements thru gmail. Now I get the same message. I switched over to yahoo and it will send one at a time. This sucks.

I am having the exact same problem starting today. I only send invoices one invoice at a time, but it won't allow me to send them. I keep getting this same message every time.

I tried deleting the email address in preferences and re-entering it and it sill doesn't work.

This is a REAL PAIN!

I am suddenly unable to send pay stubs via email. My folks really need these! I am getting the message that it is a network connection failure, but absolutely no opportunity to put a password in, and connect. It just stops trying after one attempt, and closes. I have a connected gmail account, and see that this is an issue across the board. The HELP tab reads that it will prompt for password, but I never get that far. I am pained by the uselessness of this software. I spend more time fixing than I can actually getting any work done. 

We also had this problem. CS had us go into Edit, Preferences, Send Forms. Instead of Web Mail, check Quickbooks email. This worked for us. They said that on June 16 an update will address this and we can go back to Web Mail. Hope this helps.

I had a problem with error popping up for every computer at our office for sending out estimates or invoices (We have Gmail webmail). It started popping up randomly a few weeks before, but we just pushed the send button again, and it would send. Now though every time it happens.

I got it to work now, here is my fix:

For the Web Mail, select Other instead of Gmail.

Put in the stmp.gmail.com, 587, check box respectively. (Like PBWCPC says)

In Gmail, make sure you have IMAP enabled.

Make sure "Less Secure Apps" is enabled from your google account (This is what fixed it for me)

Then next time you send an email from QB, it will ask you to for your password. It worked for a couple computers in our office.

(Now I am having problem on another computer where it can't access the email server, but that is a separate company/email domain...not sure why though

Shout out to PBWCPC for pointing me to the right direction