Mac Mail Keeps Asking to Enter Password? Here’s How to Fix That

Aug 10, 2014 - 18 Comments

Mail app icon When you set up a new Mail account in Mac OS X, you typically enter the service provider, email address, and the email accounts password once, then everything just works, right? Well, generally, but sometimes things aren’t so simple, and a frustrating issue that some users encounter is Mail app repeatedly asking for their password, over and over again. This can show up either as a pop-up window requesting the password be entered again with the message “Enter Password for Account (Name)”, or in the Connection Doctor feature of the Mac Mail app where it says the account verification or login failed, and to try again.


Mail Mail app asks to enter 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. 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. 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.

1: Double-Check the Password is Correct

First, 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. That means checking your caps lock key to see if it’s on or off when it shouldn’t be, making sure all characters are entered exactly as intended.

For example, if the email password is “Pepperoni@Pizza” but you’re entering “pepperoni@pizza” it’s not going to work due to the difference in casing. Precision matters here, as it does with virtually every form of secure password or phrase.

Enter the correct password at that Mail dialog window, and check the box for “Remember this password in my keychain” and you should be good to go, never to see the message again… but sometimes you do see it again. Ugh. If you are absolutely certain that the password is correct, but Mail app is still asking for the password anyway, go ahead and proceed with the next troubleshooting steps.

2: Manually Setting the Correct Password in Mail App

Know the password is correct with immense certainty? Let’s manually set the correct password in Mail preferences then:

  1. Go to the Mail app Preferences by pulling down the Mail menu
  2. Choose the “Accounts” panel from the Mail preference window
  3. Select the mail account from the list that you are having problems with
  4. Under the ‘Account Information’ tab, click in the “Password” field, delete the existing entry (if there is one) and re-enter the correct password here
  5. Click on the “General” tab or go to close Preferences and when asked to save changes, click “Save”

Fix for Mail asking for password constantly in Mac OS X

Now refresh the Mail inbox, does email come through as expected? It should.

Next, try to send an email, either to yourself or to someone else. Does the email send as expected? Again, it should, but if it doesn’t… move along to the next troubleshooting step:

3: Password Request on Sending Email Only? Set the Outbound Mail Server Password in Mail App

If incoming mail works fine now, but outgoing emails are still failing and you still get the password request dialog box, this likely means your password for the outbound mail server either isn’t set, or is incorrect. Most users won’t need to do this with IMAP accounts, but SMTP mail servers often have their own separate mailbox logins, thus you’ll want to check that and set the correct outbound mail password too. Back into Preferences we go:

  1. Go back to the Mail app Preferences by pulling down the Mail menu and choosing “Preferences”
  2. Select the “Accounts” panel from preferences window
  3. Choose the mail account that is throwing password errors
  4. Under the ‘Account Information’ tab, click on “Outgoing Mail Server (SMTP)” and choose “Edit SMTP Server List”
  5. Click the ‘Advanced’ tab
  6. Be sure the email username is entered properly here, then click into “Password” and enter the correct email password associated with the account
  7. Click “OK”, then close out of Preferences and choose “Save” when requested
  8. Send email again, it should now work as intended

Manually set the outbound Mail password and login in Mail app for Mac OS X

At this point email should now be functioning as intended without incident, sending and receiving as you would expect it to.

If you’re still running into problems, there’s a few other possibilities: the email account password or login details changed, the mail server(s) changed, or you signed up to use 2-factor authentication and you’re not entering the automatically generated password (a common problem for those who use the complex and safer 2-step logins from services like Gmail). These issues are beyond the scope of this article, but should give you a lead if you’re still having problems. Sometimes the best approach in those situations is to simply delete and re-add the mail account, though you’ll probably want to backup your mail messages first if you go that route. Remember, you can get a look of what’s going on and some more details about the email problem by going to Connection Doctor:

Mac Mail app requests password to verify login details of email account

A friend ran into this latter issue recently on their Mac running OS X Yosemite, they were experiencing the ‘incorrect password’ popup box constantly when trying to send emails either in OS X 10.10 and under OS X 10.9, it didn’t matter what version of OS X was being used, the outbound email never was working except when sent from their iPhone. That was a pretty good indicator that the problem was related to an incorrect outbound mail login, thus the solution in this case was correctly setting the SMTP (outgoing mail server) password in the Mail application advanced preferences – they were using AOL email which means no SMTP login at all is necessary, so removing the SMTP and relying entirely on IMAP was the solution there – and then email worked fine again for both sending and receiving from Mail app.

Let us know in the comments if you’ve had Mail app login issues on your Mac, and the solutions you found that worked for your situation.

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Posted by: Paul Horowitz in Mac OS X, Tips & Tricks, Troubleshooting

18 Comments

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  1. Greg Walters says:

    Repairing the keychain can fix a stubborn mail error if the password is incorrect too

    • The pictures/screen shots you show on this page DO NOT MATCH THE FORMAT/LAYOUT of the new MAIL “ACCOUNTS” TAB in Yosemite. Under Yosemite, the Apple Mail “Account” Information” window does not have a field for password — period Under Incoming Mail Server there is only a User Name field…
      Since your article was dated today I assumed you’ve writing about Yosemite OS.
      AND YES, HAVING THE SAME PROBLEM EVERYONE ELSE IS HAVING WITH ICLOUD POPUP WINDOWS IN MAIL — IT STARTED WITH YOSEMITE.

  2. virgahyatt says:

    Could you please explain this part a little better: “they were using AOL email which means no SMTP login at all is necessary, so removing the SMTP and relying entirely on IMAP was the solution there.” SMTP is required for sending email and even AOL requires authentication if you aren’t connected directly to their service (they are the ISP for your location).

  3. Garrett says:

    Any tips on this for iBooks? Whenever it is opened on either Mac or iPad both on current releases of the OS, it wants a password every dang time.

  4. benji888 says:

    One of my emails I get fine on my iPad & iPhone, but, I’m not sure for how long, maybe just w/yosemite beta, but, not getting mail on my mac now for that addy…I am using iCloud keychain, so it should be fluid, what to do?

  5. May Tha-Hla says:

    Am in Myanmar with same problem. Help!!

  6. david says:

    Wait…people are still using macmail? Maverick destroyed it for me. Is it back? Forget password..what I needed was an actual functional download and update..You know…I needed it to work. Details….

  7. Charleen McManus says:

    Ahhh! Problem solved, I can now send and receive email from client accounts all from my MacMail. You’re a lifesaver! Thanks a bunch.

  8. Art says:

    It may be just a timing issue; one of my accounts will work for days, then suddenly show that password-failure message. I just press [esc] to dismiss the box — no re-typing or other steps are necessary!

  9. RM says:

    getting rid of old passwords stored in the keychain could help too – this is nearly essential if you’re dealing with an exchange server.

  10. Ignite Mindz says:

    I had an issue once where I was going under accounts and changing the password. When I’d go back to accounts after being prompted again, the password field would still be blank. Had to restart the computer to make the password stick. Mind you this was 15 minutes after restarting the computer for a separate problem. I’ve found way too often that I have to delete the account to get it working again properly for a client. I suppose I’ve been lucky with not having to backup the mail first. What’s the best method for backing up mail and mailboxes?

  11. Osc says:

    The only reason this ever happens is the mail server tells mail that the password/username combo is incorrect.

    Art and RM have the right idea: multiple passwords for the same server and the same account in Keychain Access are not good.

    Ignite: Sentence 1 & 2 are because the username/password combo were refused. Sentence 3 is because the server accepted the user/password. Sentence 4 has nothing to do with the Mail issue. Sentence 5 is because the user/password were incorrect according to the server. Sentence 6 & 7 Time Machine.

  12. Essee says:

    I have had this problem on and off for 4 years now. I ignore the message. I know all passwords are entered correctly. It does seem to do it less than it used to and it does seem to appear more with my one aol email account. However the same thing happens periodically with my gmail and icloud accounts as well. I have found that trying to fix it only makes it worse.

  13. will777 says:

    hello am new to mac
    i try to setup email on the mail app but it asks for server address i have tried many address hot hotmail but nothing ?

  14. L123 says:

    This solution worked for me. I was being repeatedly asked for my AOL password and and I was unable to receive or send emails from my AOL account.

    I think this solution suggests that keychain was “confused,” for some reason, about what my AOL password was.

    1) Go to Keychain Access:
    Finder>Applications>Utilities>Keychain Access

    2) In the box at the bottom left (titled “Category”) click on “All Items”

    3) In the search field (top right), I typed in “aol”, to reveal all of the AOL related line items (since my password problem was with AOL).

    4) In the main window, look at the lines that have imap.aol.com and stmp.aol.com. There is an “@” in the left column of the main window, next to these lines.

    I had about a dozen of these lines items. For each line item, I did the following:

    5a) Double click. A window appeared.

    5b) At bottom left, check the box to the left of “Show Password.”

    5c) A window appears asking for the “keychain password.” I used my user account password, the one I use to log onto my computer. Mine is an administrator password.

    5d) The password is revealed!

    5e) Is the password wrong? If yes, then (a) exit out (press red button at top left), then (b) right click the highlighted line item, and (c) select the delete option.

    5f) Is the password correct? If yes, exit out (press red button at top left).

    6) Repeat step (4-5) for each imap.aol.com and stmp.aol.com item, until you have only one imap.aol.com and one stmp.aol.com, each with the current, correct password.

    Shortly after I did these steps, my “Mail Connection Doctor” gave a green dot for the status, all of my mail arrived, and I could send emails.

  15. richard says:

    Works great, THX!

  16. Steve Cournane says:

    Macmail is a horrible program that should not still be used. I have tried to figure this problem out but it just does not go away. Why? because the programmers simply do not care.

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