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2: Fix Outbound Email SMTP Failures in Mail App Manually on Mac

If you’re still experiencing Mail problems with stuck outbound messages and SMTP server errors, move to the next trick. Once that email goes through, you may have some unsent messages sitting in your outbox, they will send automatically in time, but you can also synchronize the mail account to push it along.

Compose a new email message and send it (to yourself, us, your Mom, Santa, whoever, this is just a test email).

Now click “OK” and close Preferences, selecting to “Save” when asked about changes.

Re-enter your login and password credentials for the affected email account here.

Select the ‘Advanced’ tab at the Edit SMTP Server List screen.

Look under the ‘Account Information’ tab and click on “Outgoing Mail Server (SMTP)” and choose “Edit SMTP Server List”.

Select the mail account that is experiencing problems and/or errors.Choose the “Accounts” tab in the preferences window.Open Mail app and go to the Mail menu, then select “Preferences”.If you’re getting cannot send mail errors only when trying to send mail or connect to your emails SMTP server, the solution is probably the same as when Mail repeatedly asks for a password, you simply need to re-authenticate and provide the SMTP server your login and password as set in the mail preferences: Keep that in mind as you work through this process.ġ: Fix Sending Mail Errors in Mac OS X with Credentials If you are using 2-factor authentication, you need to generate an app-specific password from Google here and use that in troubleshooting solution #1 rather than your normal account password. If you’re experiencing any of these issues with Mail app, the solution is likely simple as we’ll show you.Ī quick note for Gmail users experiencing an inbound or outbound mail problem, a connection failure, or an error message that says that Mail “Cannot send message using the server .” or “The Gmail SMTP connection to server failed.” While either of the solutions outlined here are likely to resolve the problem, it’s also possible that you are experiencing the error if you’re using 2-Factor Authentication on the Google account. Typically this is in the form of an SMTP server connection error, a mailbox that’s seemingly stuck offline, a repeated request for a password from Mail app (a fairly common issue which we’ve fixed before), or some other connection error.

Some Mac users who updated MacOS have found Mail app to experience errors or problems when trying to send email.