2 Possible Fixes for Mail SMTP Sending Errors on Mac OS

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Some MacOS users who have upgraded to MacOS have found errors or problems in Mail when trying to send e-mail. Typically, this is in the form of an SMTP server connection error, a seemingly offline stalled mailbox, a repeated password request from Mail (a fairly common problem we’ve fixed before), or some other connection error. If you have any of these problems with Mail, the solution is probably simple, as we’ll show you.

Quick guide for Gmail users who have a problem with incoming or outgoing mail, a connection error, or an error message stating that Mail “Cannot send message on smtp.gmail.com.” or “Gmail SMTP connection to smtp.gmail.com failed.” While either of the solutions outlined here is likely to resolve the issue, it’s also possible that you may have an error if you’re using two-factor authentication with a Google Account. If you’re using 2-Step Verification, you’ll need to create an application-specific password from Google here and use it in Troubleshooter 1 instead of your regular password. Keep this in mind as you work through this process.

1: Correct transmission errors in Mac OS X with login information

If you can’t send mail errors just when you try to send e-mail or connect to your e-mail SMTP server, the solution is probably the same as when Mail repeatedly asks for a password, all you have to do is re-authenticate and enter the SMTP server user name and password specified in your e-mail settings. :

1. Open the Mail application and go to the Mail menu, then select Settings
2. In the settings window, select the Accounts tab
3. Select an email account that has problems and / or errors
4. On the Account Information tab, find “Outgoing Mail Server (SMTP)” and select “Edit SMTP Server List”
5. Select the ‘Advanced’ tab on the Edit SMTP Server List screen
6. Re-enter your login and password credentials for that email account



7. Now click “OK” and close Settings, select “Save” when prompted for changes
8. Write a new email and send it (to yourself, us, your mom, Santa, anyone, this is just a test email)

The email should now be sent as usual.

Once your email has gone through, your inbox may have some unsent messages that are automatically sent on time, but you can also sync your email account to push it forward.

If you’re still having email issues with stuck outgoing messages and SMTP server errors, skip to the next trick.

2: Manually fix SMTP errors in outgoing email in Mail on a Mac

The trick above should work and solve your problem, but if you’ve confirmed that your login and password are set and accurate and you still find yourself struggling with Mail, which can’t send emails and your Outbox fills unsent emails, another possible solution was found by Apple support forum user. Note that this is a modification of the email account to allow insecure authentication, which is a potential security risk, making this an unsuitable solution for some users. If this is due to an error in OS X Yosemite Mail, it is likely that a fix will be released to fix the problem without you having to edit any plist file yourself. This is a little more advanced and you’ll probably want to back up your Mac (or at least the Accounts.plist file) before you change anything here:

1. Exit Mail
2. In Mac OS X Finder, click Command + Shift + G and type the following path:

~ / Library / Mail / V2 / MailData /

3. Make a copy of the “Accounts.plist” file on your desktop – it acts as a backup in case you break something, just replace the file



4. Open the file named “Accounts.plist” in the text editor of your choice
5. Find the following line:

UserAllowsInsecureAuthentication

6. Replace “false” with “true” so that it reads, and then save the Accounts.plist file



7. Close TextWrangler or TextEdit, and then restart Mail
8. Try to send the email normally, it should work normally

As already mentioned, this is making a change that allows for potentially insecure authentication for that email account, making it impractical for users who live exclusively on public Wi-Fi networks or high-security risk environments.

If you have multiple accounts set up in Mail that are having problems, you’ll need to find the account you’re having problems in in the Accounts.plist file. Of course, if the problem occurs in all accounts, you want to make a change to all accounts that run with failed SMTP responses.

Did # 1 or 2 solve Mail problems with MacOS or Mac OS X? Can you resend and receive email as usual? Let us know in the comments.

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