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1: Double-Check the Password is Correctįirst, and this may be sound silly and you’re probably already annoyed by the suggestion, but be absolutely sure you are actually entering the correct password. Whatever the case, if you’re having the repetitive ‘enter password’ message in the OS X Mail app, read on and you should have it fixed in no time.

By the way, if you experience exactly that, it’s a good indicator of what’s really going on… the password is probably entered incorrectly somewhere, or not being saved.

Then, click ‘Save Password.To make matters even more confusing with the repetitive password request, when the password is entered at the pop-up dialog, sometimes that popup dialog box goes away and the Mail app works as intended… at least until the Mail app is relaunched or the Mac has been rebooted. With your password typed in the field, click on the keychain icon. Note: If you’re already logged in, log out of the account. Next, type your login credentials but don’t click ‘Login’ just yet. First, open Safari and go to the website of your choice. If you’re skimming through your passwords in Apple’s Keychain and notice that some are not accurate or up-to-date, you can easily remedy this. What do I do if a password is outdated in my Keychain?

Now, you can try to log into Keychain again using the same password that you use to unlock your Mac. Click on ‘Keychain’ in the far upper right corner of your Mac. You’ll need to set the password back to default (which means your Mac unlock password). On the off chance that you can’t access your Keychain from your Mac, you aren’t completely out of luck. My Mac unlock password isn’t letting me access Keychain. Here are some more answers to your most frequently asked questions.