Hi there iteachmusic,
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Failed to verify the server certificate. This could be because of your network configuration or your proxy settings.Update. This is likely caused by Avast Web Filtering being enabled and blocking Gmail web access for adding a mail account in Mac Mail.
Thanks for using the Apple Support Communities. I understand you’re having some issues using your Gmail account with Mac Mail. I’ll be happy to help with this.
First, if you only want to use Gmail, not iCloud, that’s fine. To ensure you don’t have iCloud enabled, open up System Preferences > Internet Accounts then select iCloud from the group and make sure Mail is not checked.
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Once you’ve done that, take a look at this article for what to do if you’re getting the Login Failed message due to a password issue on your Gmail account:
This link provides some helpful info regarding the issues you’re running into as well:
Account Error Mail Mac
Best wishes.
Apr 23, 2019 10:56 AM
If your Mac is connected to the Internet but suddenly stops sending email, you should generally try again later, and if necessary work with your email provider to resolve. If you're using Apple's iCloud Mail, learn how to resolve issues with iCloud Mail.
Gmail Login Failed Mail App MacCheck for status messages
You might see a status icon such as a lightning bolt or warning symbol next to your account's inbox in the Mail sidebar, or in the upper-right corner of the Mail window. Click it to learn more.
Mac Mail App Login Failed![]() Test using webmail
Many email providers offer webmail, which is a way to use email with a web browser such as Safari, instead of with an email app such as Mail. For example, if you're using an iCloud Mail account, you can use iCloud.com to send and receive email.
Webmail is a good way to verify that your account is valid and you can sign in to it from the web, but it doesn't mean that your account is set up correctly in Mail. Your email provider can help you verify your email settings and check for other issues that affect sending or receiving email.
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