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Mail authentication failed

I have a macbook pro Retina 15 in, operating on Mojave. Since last night I have been experiencing problems with my Mailbox. I have three e-mail accounts linked to my mailbox. Since yesterday I am constantly being asked to enter the password for two of these accounts (google and yahoo), but when I do I receive an error message saying Authentication Failed. There is no doubt that I am entering the correct password, since I can access my accounts normally from the browser. If I select the option to take all accounts online then the problem goes away, but it soon reappears.

Is there anyone else having a similar problem? What seems to be the reason for that?

MacBook Pro 15", macOS 10.14

Posted on May 2, 2019 6:19 AM

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Question marked as Top-ranking reply

Posted on May 2, 2019 8:23 AM

lafidaarrmida wrote:

I have a macbook pro Retina 15 in, operating on Mojave. Since last night I have been experiencing problems with my Mailbox. I have three e-mail accounts linked to my mailbox. Since yesterday I am constantly being asked to enter the password for two of these accounts (google and yahoo), but when I do I receive an error message saying Authentication Failed. There is no doubt that I am entering the correct password, since I can access my accounts normally from the browser. If I select the option to take all accounts online then the problem goes away, but it soon reappears.
Is there anyone else having a similar problem? What seems to be the reason for that?


From Mail>Window>Connection Doctor>Show Details


see if there is more info there on the issue.

Use Mail Connection Doctor - Apple Support



2 different accounts is suspects.


rebooting the computer

deleting the mail accounts and adding them back in.

Check your keychain Access.app for old passwords associated with the account(s) and delete those.

reboot the router.

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1 reply
Question marked as Top-ranking reply

May 2, 2019 8:23 AM in response to lafidaarrmida

lafidaarrmida wrote:

I have a macbook pro Retina 15 in, operating on Mojave. Since last night I have been experiencing problems with my Mailbox. I have three e-mail accounts linked to my mailbox. Since yesterday I am constantly being asked to enter the password for two of these accounts (google and yahoo), but when I do I receive an error message saying Authentication Failed. There is no doubt that I am entering the correct password, since I can access my accounts normally from the browser. If I select the option to take all accounts online then the problem goes away, but it soon reappears.
Is there anyone else having a similar problem? What seems to be the reason for that?


From Mail>Window>Connection Doctor>Show Details


see if there is more info there on the issue.

Use Mail Connection Doctor - Apple Support



2 different accounts is suspects.


rebooting the computer

deleting the mail accounts and adding them back in.

Check your keychain Access.app for old passwords associated with the account(s) and delete those.

reboot the router.

Mail authentication failed

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