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


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.

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:

Go to the Mail app Preferences by pulling down the Mail menu
Choose the “Accounts” panel from the Mail preference window
Select the mail account from the list that you are having problems with
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
Click on the “General” tab or go to close Preferences and when asked to save changes, click “Save”

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:
Go back to the Mail app Preferences by pulling down the Mail menu and choosing “Preferences”
Select the “Accounts” panel from preferences window
Choose the mail account that is throwing password errors
Under the ‘Account Information’ tab, click on “Outgoing Mail Server (SMTP)” and choose “Edit SMTP Server List”
Click the ‘Advanced’ tab

Be sure the email username is entered properly here, then click into “Password” and enter the correct email password associated with the account
Click “OK”, then close out of Preferences and choose “Save” when requested
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.

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.



16 Jan 2019 - 22:23

Who's new

  • Joris
  • OCS
  • locje
  • Charlotte
  • Rutger Westen
  • Martijn van Beek
  • FUH
  • Rozemarijn
  • Eveline
  • Kevin Verburg

"No taste..."

"The only problem with Microsoft is they just have no taste."

* Steve Jobs in 'Triumph of the Nerds' (1996)

Crew Onboard

There are currently 0 users and 172 guests online.

Recent comments

Popular Callsigns

Disclaimer is 'Affiliate Free'  We are totally independent and have no affiliations with Apple, Boeing, TESLA or any other gadget provider what so ever. We reserve the right to refer to ourselves as ‘we’ and be as partial as we like. If you don't like that, stop consuming our bandwidth.
Have a good flight...

Company Freq.

You're not permitted to post shouts.
Willem-JanSinds 2 dagen werkt iTrans niet meer bij mij, is er een update ?? gr, WJ17 May 2017 - 08:24
Willem-JanGoedemorgen all,17 May 2017 - 08:24
KoenBeste trapple, Heb sinds kort een one plus 3t met android versie 7. Als ik in de standby app een datum wil selecteren dan sluit de app zich. Daarna moet je alles weer invoeren oftewel de app is niet te gebruiken. Groetjes, Koen Schimmel11 Feb 2017 - 11:17
AwesomeThx, Cees, for your donation to keep TRApple & eTRA safe and stable.27 Mar 2015 - 10:33
Awesome@steven: Feb 2015 - 18:53