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Buy nowThanks 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:
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:
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.