Mail Keeps Rejecting Password (updated)

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I dread the days when Mail decides it doesnt want to work properly. This particular bug drives me insane. Mail keeps rejecting my email password, even though its correct, to the point of utter insanity.

Every couple of weeks, Mail will actually interrupt everything with a dialog box telling you that your e-mail password is incorrect or has been rejected, and asks that you re-enter the password –even though the existing password is perfectly correct, of course! Each and every time Mail fails to connect to the server and you are left without new emails. Its ridiculous.

Enter Password for Account [account name]

The server [server name] rejected the password for user [username]. Please re-enter your password, or cancel.

Don’t waist time re-entering your password. Theres no point. Theres nothing wrong with your existing password. The problem isnt specific to any one email account provider, say Gmail. Any email account is susceptible to this bug. The problem lies with Apples Mail application and not the email provider.

Some users believe this bug has to do with Mail not being able to handle server time-out correctly. I though have no clue why it happens. Neither does Apple; the problem has gone unfixed for years.

Side note: restoring messages

In trying to troubleshoot, I even went as far as deleting Mails preference file. Bad/Stupid idea! All my email accounts and messages where gone when I started Mail again. By chance I discovered an easy way of quickly restoring email messages. To simply rebuild Mails database of email messages, first quit Mail, then move the file Envelope Index from ~/Library/Mail to the Desktop. Upon restarting Mail, all messages will be reindex and added back to the appropriate inboxes.

No Solution in Site

Apple has no solution to Mail randomly rejecting your password. According to an Apple article:

This message may appear several times while trying a correct password.

This can happen if the mail server is not available for authentication or cannot be contacted. Click Cancel, then wait a few minutes. After waiting, choose Go Online from the Mailbox menu, then enter the same password.

Bullshit. The server is working perfectly fine, according to both Entourage and Thunderbird.

So I am stuck today without any new mail in my application of choice and forced to use Safari and Gmail Notifier. I have no idea what exactly the problem is nor any clue when it will go away. The the most common suggestions do not work: deleting the email account passwords from my Keychain and performing Keychain First Aid.

While there are tips and tricks to resolving this problem, theyre all just voodoo. Nothing really works. I have therefor resorted to typing in profanities directed at Apple each time Mail interrupts me with the password dialog box. It may not fix the problem, but at least Im relieving some stress.


Update solution

April 27, 2006. Two weeks later and Im still experiencing the same problem. I had my suspicions that their was something very wrong with my Keychain. I already had tried many times using Keychain Access to delete all entries that contained and were listed as an Internet Password. That never work, so I tried something more drastic.

  • Quit Mail and returned to Keychain Access.
  • Deleted the entries associated with the email accounts (In my case I searched for and deleted those listed as Internet Password).
  • Quit Keychain Access. Open: /User/username/Library/Keychains
  • Move login.keychain to the Desktop
  • Open Mail. It asks for the account POP password.
  • After entering the password and opting to save it, a dialog appears: A keychain cannot be found []. Select Reset To Default, confirm Yes and then enter the login password.
  • Almost miraculously, Mail stops prompting for the email account password and downloads all new mail.
  • Quit Mail. Move login.kechain back to /User/username/Library/Keychains
  • Return to Mail. It will again ask for the account password, but this time it will save properly and hopefully for good.

Does the above appear a little extreme and seem like useless Mac Voodoo? Yes, but it works and Im no longer complaining.


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  1. 1coelomic
    I have had the same trouble with mail and always thought that my password was wrong. Thank you for the tip.[Andrew responds: What tip? : ) Id love to find a solution to this, since Im clearly not the only one suffering from this.]
  2. 2David
    I always just delete the account entirely in preferences and then re-enter it. Frankly Ive not encountered this problem that often, but thats what I do when it has happened. I dont think I lost any mail that way though maybe I did its been too long ago.
  3. 3Stridey
    This happens to me all the time. As far as I can tell, the only solution is to hit cancel, and tough it out until decides to play nice again.
  4. 4Matt
    I thought that I was the only one who encountered this problem! I access 5 pop accounts all the, and love Mail for it. However, I get this random password problem at least once a week from every one. The account that gives me the most trouble is my Hotmail account. Granted, I have this setup via MacfreePops, so I thought this always dealt with the problem.I recently go so fed up with all the effort that I had to put into Mail to get it to cooperate, that I made a huge decision and jumped the boat to Entourage. Right now Im fairly impressed with being able to keep all my contacts, calendars, and email in one spot. Im also playing around with the Project Center. However, I still prefer Mail and miss it somewhat. If only it would just work!
  5. 5Al
    I too have suffered from this problem a long time. Come on Apple –fix the problem![Andrew writes: I took the liberty of adding grammar to your comment. ; ) ]
  6. 6Matt Schinckel
    I thought it was issues with my connection being full, it seems to happen more when Im using more of my bandwidth. Interesting to note it happens to people not on dialup!
  7. 7Kuswanto
    Sometimes i get that message too. But i didnt re-enter my password. Actually this is not just a Mail bug. I was experience the same thing when using Thunderbird. Its because of bad connection (time out).[Andrew responds: No. Its specifically Apples Mail app. If it was a timeout issue it would happen a few time and go away. This issue is specifically isolated to Mail.]
  8. 8don
    I have suffered from the Curse of the Rejected Password syndrome many times and I noticed a solution that seems to work for me.For some strange reason when I go to the Mails preference pane, then go to my account info box, there seems to be a second (Why????) smtp.address in the outgoing smtp. box. I have no idea as to why or how I end up with a second outgoing duplicate of my smtp. address , but if I simply delete one of them, the problem seems to go away? At least, up to this point.

    So, you, may try, like myself, checking the outgoing smtp. box and deleting any duplicate smtp. address.

    Good luck on this nagging buggy bug.

  9. 9Kheldar
    Same here, although it only happens with my account while the, and other POP accounts are fine. Glad youre back online Andrew, I was waiting for your Mail Stamps download to come back online so that I could use it. I recently switched from Entourage and except for small kinks, I love the interface and the search speed of Mail.
  10. 10Martyn Phillips
    I run into the same problem a couple of times a week when using mail with my yahoo email account. Its annoying, but I find that just reentering my password resolves the problem.I submitted a request to Apple that they modify the dialog box and add a retry button. Wouldnt fix the problem, but it would make it a little easier to live with.
  11. 11Poster
    I, too, suffer from this vexacious bug. Im on DSL (I know, it sounds like being at some kind of Narcotics Anonymous meeting) and Im fetching email from only one account. I have no idea what causes it, but it usually goes away after 2-3 tries.[Andrew adds: vexatious: causing annoyance, frustration, or worry nice choice of words.]
  12. 12Ian O
    I find the problem occurs most frequently when Mail accesses a pop server thats notoriously slow normally, suggesting its a time-out problem. The solution would be to extend the length of time Mail is prepared to wait for the server to react. THAT, I suspect, is something only Apple can do. Im surprised at the suggestion that Apple have no clue as to why it happens.Possibly you struck some droid within Apple with insufficient clues to pass it on to someone who does.
  13. 13Tom York
    When I encounter this problem I quit mail and re-start it. This seems to fix it for me. Nonetheless, it is very annoying.Chers.


    Andrew writes: I took the liberty off adding grammar to your comment.

    Off ~ away from the place in question etc. etc.
    Of ~ expressing the relationship between a part and a whole etc. etc.

    [Andrew laughs: Yes, Im an idiot. Ill admit it.]
  14. 14Matt E.
    I get this problem occasionallyIve looked for solutions with no helpWhat I do is hit the cancel button until the popups go away, quit Mail, re-open (I can do this immediately and it works fine..), and Go Online with the accounts again.and it wont ask me for the passwords.

    I seriously hope Apple fixes this soon, it pisses me off.

    Glad to know though I am not the only person with this problem. :\

  15. 15Lars
    Tom is right. The only sure cure is to quit Mail and restart it.Ive been using (and endorsing) Apple software for 15 years BTW, and this bug is the most bizarrely neglected and irritating non-OS screwup Ive ever come across: and, to cap it all, in arguably the most important app in the dock.

    Anyone from Apple listening?

  16. 16Brian Watson
    Im a sufferer, but Im not sure that it is Mails fault. I have two accounts, and this only ever occurs with one.Ive deleted both the second entries of smtp.addresses. Ill see if that helps.
  17. 17MalEbenSo
    I also observe this behavior with only one account. It is a free e-mail service and limits POP-requests to one per 15 minutes plus requires POP-before-SMTP-authentication. I suspect that this is part of the problem, although I have successfully sent multiple mails independently within one 15-minutes-slot.
  18. 18Andrew Escobar
    Im still waiting for Mail to play nice. No luck yet, but the bug only gets more interesting. When checking for new mail using POP:

    • andrewe@[gmail] does not work in Apples Mail
    • andrewe@[gmail] does work in Entourage and Thunderbird
    • andrewescobar@[gmail] does work in Apples Mail

    So now all email addressed to account is forwarded by Gmail to account andrewescobar. Its the only way I can get new messages into Mail.

  19. 19Jose Manuel Araque (Jaguar) has a number of bugs that I consider to be LETHAL:

    1. It took me weeks to move my Thunderbird mailboxes to because the Import feature did not handle properly. I should have known then never to move my mail into because I never had any problems with Thunderbird. But I was enticed by the promise of live Search capabilities.
    2. I have not been able to move to Tiger because in Tiger failed to import the 20,000+ messages in my Sent.mbox. I have waited, and waited to see if Apple would fix these bugs, but
    3. Sometime in the past 6 months, while waiting for these fixes, decided to silently DROP 66% of my Sent.mbox (dont ask me exactly when). I lost all my Sent history from 2002 through 2004. If you look around you will find plenty of postings about dissapearing mailboxes, corrupted mailboxes, etc.

    This is simply UNNACEPTABLE behaviour from any program I use, but Mail in particular is the neural center of modern communications. Even my 70+ year old mother has an email address. Emailing is the most important application in Consumer computerts today. Apple is treating Mail as a second rate app.

    I am going back to Thunderbird after this very painful experience.

  20. 20Jose Manuel Araque
    Correction: I meant did not handle Carriage Return and-or Line Feed correctly
  21. 21Gomi
    This bug hits me at least once a week when sending messages I always thought there was something wrong with my server. Noticed though that POP3 accounts are the most susceptible
  22. 22Steve Tovell
    I have had this problem ever since I got my first iMac a few years ago running 10.2. At the time I was collecting numerous POP3 accounts and they would randomly come up with the annoying password prompt.Time passes and now im on 10.4.6 on a new iMac and have my own POP3 server upstairs. My wife has her own iBook. We both collect our mail from the POP3 server, and if either of the Macs try to collect at the same time, one of them will get the password prompt. I just click go online to get round it. It definitely seems to be a time out issue. I even set up my mobile phone recently to collect my email from my server, and that caused Mail to time out as well.

    I dont think its the server, which is 602 Lan Suite on a XP box. Its definitely Mail. Maybe Apple will fix it in 10.5.

  23. 23Richard
    I never have any problems with my Mail app? I have two accounts, both POP3. One with the Bluebottle email service provider, and the other my own website server. Im running 10.4.6, with all updates installed. I have several hundred emails in each box.Am I the only one who never has problems with Mail?
  24. 24Richard
    Update: I think the password error may be caused if the server causes the Mail application to queue for collecting or sending email (a busy server). Usually most applications would wait their turn for the connection to the server to open, but mail seems to assume that it is a password rejection.Bluebottle are a relatively small email company – this might be why I have never had this problem with them. And as for my own server account – I am the only person ever to access the server at any one time.
  25. 25Sophie
    I feel for you guys I just had this INSANE password problem this morning. MSN messenger, hotmail, Entourage none of it works anymore. I tried to restart them and its the same. It says my old keychain password aint recognized anymore. I said OK to reset to defaults and it still wouldnt work. Can anybody tell me about where I can find this Mail’s preference pane, then go to my account info box, there seems to be a second (Why????) smtp.address in the outgoing smtp. box. Don was talking about?I am pulling my hair out! Thanxs for any help.
  26. 26Jared
    I also have the same problem, but I used to get it with outlook and only with my yahoo accounts. I do agree it seems to be a time out problem BUT then how can it only be mail thats the problem. Infact outlook was worse than mail. It would reject it every second time outlook would check for mail and why only with my yahoo accounts and not my ISP one.I find that when the prompt comes up, i just hit cancel then the Get mail button and it works again. I never have to restart Mail. Bu that may not work for everyone.
  27. 27Dave
    Pain in the arse aint it. Like someone else has said I find that you cancel the dialog box, quit, restart and then put the offending account back online. So far (eek) its worked for me
  28. 28NoOne
    Time for thunderbird?
  29. 29Andrew
    I finally found a solution that worked for me, posted above. Its a little extreme and involves some Mac Voodoo but it works. It may or may not work for you. (You may loose your saved passwords if youre not careful.)
  30. 30J-Bird
    Quick fix:A) Repair permissions in Keychain:

    1. open Keychain
    2. Option-Command-A
    3. Select Repair and click Start

    B) Delete any old gmail info from your keychain

    C) Delete all gmail accounts from your Mail app

    D) Recreate all gmail POP accounts in Mail app

    Everything works smooth again!

  31. 31Andrew
    I tried repairing the keychain, but it fixed nothing.Deleting then recreating email accounts in Mail? Ouch! Its a much more involved process, and again it didnt work for me.

    Try my solution. Its painless.

  32. 32Rene
    Does anyone out there have a real fix for this password problem?
    Does Apple even care that we are having this problem?
  33. 33Hans
    Same problem here, but I do not have a login.kechain (Tiger 10.4.6). Any other fix ?
  34. 34wardee
    Many thanks for the help and advice. Very reassuring to know that many others have experienced the same problem; I thought I was quite alone in having – and failing to resolve – the password problem.After two fruitless days I found, and tried, your solution to the password problem. It seems to be working. So far, in the last hour, I have had just one password request – a huge improvement if not a total solution yet.

    (One point: when I carried out the following step:

    Quit Mail. Move “login.kechain” back to /User/username/Library/Keychains,

    a “login.kechain” file was already there. Should it be left, or replaced with the file moved to the desktop earlier? Or does it not matter?)

    Anyway, many thanks for all the help. I have bookmarked your site and will be returning.

  35. 35Hans
    Well I tried the keychain solution, does not work here (10.4.6). Even from a brand new account and running AppleJack AUTO (drastic).Thks anyway
  36. 36Michael J.W Beijer
    problem solved:

  37. 37Jason
    I have had this problem also, and after alot of time spent trying to figure it out I think I have discovered the problem. my mail server will only allow 60 connections per hour ( I assume that most mail servers have a similar rule). if the mail program tries to connect more than that it will be rejected from connecting and macmail sees this as a failed password. mail was doing this yesterday, so I tried connecting from another mail program and got a 60 connections max per hour response, I waited untill the error stopped coming up and tried connecting with mac mail again, and it worked first time! I have tested this another time now and I got the same result, I connected 60 times untill I got the password prompt. I kept trying and exactly an hour later it started working again. I am not sure if this is the same problem for everyone but it seems likely.
  38. 38Rich Salter
    Hi there folks,I found this page as Mail (2.1, OS X 10.4.7) kept doing the same thing to me: asking for (and rejecting) my correct password every time it tried to check my main POP account.

    I did the usual Keychain deletion thing, and ended up installing Thunderbird as a last ditch measure. It wouldnt work either.

    So I contacted my web hosts, Pair, and they asked me if I had a lot of emails on the mail server, as sometimes that can cause problems. Turns out I did, including some from clients whose attachments were over 15MB. After deleting those (via mail2web), everything worked fine 🙂

    Dont know if that might help anyone with troubleshooting.

  39. 39Damon
    I realise that this isnt a fix for everyone, but if you possibly can, switch your POP for IMAP. Most good IMAP providers will go and retrieve your POP mail automatically anyway. POP, in whatever variant, is evil, old and wrong.
    I use Fastmail which sycs beautifully with Mail, but clearly there are loads of others, many free or very low cost. If you cant afford to lose mail, ever, then you shouldnt be using POP. Moving either e-mail provider or between mail apps then becomes a cinch too
  40. 40Walter Dufresne
    The promised synchronization features of Apples Dot Mac and Apples Mail caused me to give up using CTM Developments PowerMail, which never hiccuped once when querying a dozen pop and imap accounts. I miss PowerMail.
  41. 41Robert
    Thank you Michael Baijer (36). That works.
  42. 42MIsha
    What worked for me just now was:Preferences > Accounts tab > Advanced tab > Clicking the remove now button to remove old mail from the server.

    I had 1600 old messages this week that I had not yet removed (it removes them automatically after one week. It connected to the server fine to remove the messages and after five minutes mail checked the account for new messages (while it was still deleting old messages) and it worked fine.

    This may give apple some clue of why their mail is not always working properly.

    Ill send it along.

  43. 43David
    Ive been reading this thread and searching endlessly for a fix because my password was rejected for over two weeks. Nothing helped, not even the update solution by Andrew. However, Michael J.W Beijer link to unlock something in gmail did the fix and my email instantly worked without the password being rejected! FINALLY! I would recommend trying this for GMAIL users (only) first.THANKS Michael J.W Beijer!
  44. 44John G. Dargie
    I havent specifically tested this out, but I think I get this error on my Mac because it tries to connect to my POP account at the same time as my PC (Windows) is connecting, and gets a failed connection for that reason.However Mail (on Mac) is the only mail application Ive come across that wont just go away and try again later with the same password!
  45. 45Justin Miller
    Im not sure why this happens but i can say it seems linked to the mail provider. We have around 20 Macs in different locations and they all started asking for the password at exactly the same time. We traced it to the mail provider and they fixed their problem Now 14 of the Macs still ask for the password approx every 3 times even though the provider no longer has any issues. Tried new mail settings, mailboxes, different connecting ISPs..nothing works.
  46. 46Daffyd
    Michael J.W Beijers trick did it for me (using Gmail). Thank you, thank you, it was driving me insane
  47. 47Nathan Nelson
    Justin, weve had exactly the same. The ISP providing the POP mailboxes had a problem, repaired the issue, and although some of our customers are now ok, Ive got a couple of sites with around twenty macs still asking for a password. Ive deleted the keychain item for the mail account, repaired the keychain and recreated the mailboxs on the server with no effect.Recreating the mailboxes on the Macs themselves is out of the question as some of the Macs hold several gig of email numbering into the thousands.

    I will try the suggestions on this page and report back.

  48. 48LEE
    I too am plagued by this with Apple Mail. I use a personal email server, and am not even going to bother trying to fix this. Its ridiculous, and as much as I love Apple, they lose serious points for this. Instead of introducing templates in Apple Mail for OS Leopard, why not introduce an application that isnt so troublesome with POP mail? Rant end.
  49. 49sankara
    Michael J.W Beijer’s trick didnt work for me i have gmail which has been working fine with mail until just now, now i can recieve but not send emails: i am constantly asked for my password, which is obviously correct. i have tried everything suggested here and none of it has made any difference yet
  50. 50Todd
    None of the suggested solutions listed here have worked for me. I have Tiger and cant get the damn pop up window to accept the password.
  51. 51Jenny
    Yes, yes, its the overstuffed mail on the server that did it for me as well. Idiotic Mail wiped out all my inbox messages, though, and seems to have deleted the mailbox in the library. This happened to anyone else? Thankfully i saved all the ones I needed in foldersThanks for the advice. How annoying.
  52. 52Bob
    i use pop on gmail and when this happens i just quit mail and then reopen it in like 5 minutes and everything is fine.
  53. 53Matt
    I have the same problem on Mail 2.1 going to a 10.4.7 server. Yesterday, my password just started getting rejected out of NOWHERE.Whats stranger is that I can use other accounts and they work just fine, its merely mine that is failing. I tried the Keychain procedure and the problem persists.

    I installed the BRU agent on the server the day my password started failing, but there is no way that couldve affected this

  54. 54Matt
    SOLUTION FOUND (sort of):Regarding my last replyI logged onto the mail server itself and blew away my cached user info in Netinfo (strange since Im running Open Directory and this server was an open directory replica).

    LO AND BEHOLD, my mail is back!! Go figure

    (I also had to change ownership of my user spools cyrus.* files from root to cyrusimap, but that was not related to this specific issue)

  55. 55rcfa
    The problem with Apples mail is that you get a generic error (password error) for all sorts of error conditions that have absolutely nothing to do with the password.
    In other words, if for ANY reason the connection fails, the error percolates back up and the only level at which the error is handled is in the code thats responsible for authentication, so you get a password error.
    As a result, to try to find a single solution to a multiple problems that happen to have a single symptom is bound to fail.There are many issues that can lead to the same result:
    – temporary DNS lookup failure
    – temporary mail server outage
    – if you use NAT and the mail server limits the number of connections from the same host, but you have multiple machines behind a NAT firewall that access the same mail server you will have trouble until you increase that limit
    – if the mail server has a limit on how often you may connect in a given slice of time and you exceed that, you will have that problem
    – if your password has changed you will have the problem
    – if your network connection is faulte (e.g. MTU mismatch) you will have that problem
    – if you have a stateful inspection firewall that terminates a connection after a certain amount of inactivity thats shorter than what Mail assumes youll likely going to have that problem,

    The real problem is, that we dont have proper error handling in the first place and thus dont get a precise error message that reflects the actual reason of failure, if need be, including quoting the mail servers error message.

    I filed a bug report with Apple ages ago, but if they will act on it, thats in the stars

  56. 56Ryan
    Just for information, I get this error with Outlook as well as Mail usually at around the same time. It is always specific to ONE of my e-mail accounts never happens to the others. I dont think its a mail problem although it would be nice if it just remembered the password and tried again later. Its annoying to have to retype every time.On the upside however, at least I remember my password. I probably woudnt otherwise because I never use it.
  57. 57Mary Lee
    I get this all the time with my .Mac email address! All my iMap account are fine, but my pop .mac account is constantly doing that. It will go along just fine for awhile, but usually about once a day it starts this annoying pop-up. I just Cancel and try again later. Sometimes it works, sometimes it doesnt. So IF this is server timeout related then I am paying way too much for my .Mac account as it is constantly timing out!
  58. 58Happy Guy
    Yes, the google reset (msg 36) works!!!!
  59. 59Jason
    Duplicate SMTP thing seems to have helped here.
  60. 60David Day
    Ive been having this problem for about 2 weeks now, it has been working fine for the last 2 years. Yesterday I did a complete erase and reinstall of OS X thinking this would solve the problem ,it didnt.Even completely erasing your hard drive and re-installing the OS will NOT fix this problem.

    Any more ideas? Im using POP on Yahoo.

  61. 61tom stavrou
    GreetingsGlad to see others having fun with mail. Ive got the timeout problem too, I tried to use thunderbird for yahoo mail and it also timeouts. Maybe its a coincidence or maybe the issue is beneath the application layer?

    Any thoughts?


  62. 62garboslover
    I cant take it anymore, please Mail stop asking me to enter my **ing pasword, please! Its been 4 days and Im going crazy. One POP account with Yahoo is accepting mail and has no problem and the other two will not accept passwords. Please, when I return to the computer, let Mail work again! I beg you, computer god(s), please.
  63. 63Tina
    MacBook Pro
    OS X 10.4.8
    Gmail pop accountWe had the same issue of a rejected password (from out of the blue).
    Tried resetting the Keychain Access without success.
    Unlocking the Google captcha, as linked in #36, was the solution. Thank you Andrew for this page and Michael J.W Beijer for the solution that worked for us. Cheers.
  64. 64Iain
    Two days ago I set Check for new mail to every 30 mins rather than every 5 mins. Hasnt asked for a password since.
  65. 65Nick
    This worked for me:My problems were between Thunderbird and Yahoo!

    Heres what you do

    Set up your account as you already have probably done in the place you want to check your email (in my case Thunderbird).

    Then you get your lovely error message when you want to check your mail.

    In Yahoo!:
    – go into My Account and login
    – go to the right side panel under Options and select Mail

    Under Management, click POP Access and Forwarding

    Click the circle beside Web and POP Access and SAVE (but before you save, click View POP settings and note the Incoming and Outgoing Mail Servers to make sure all your info is correct, and double check your PORT number for the outgoing server and make sure you set that in Thunderbird or wherever, otherwise you wont be able to send mail).

    Exit Yahoo! and in Thunderbird, or whatever you are using make sure you edit your Outgoing Server port number

    Worked like a charm for me!! Good luck!!

  66. 66Valeri Zwick
    O.k. I have this hideous mail problem ,too, but only on my laptop not on my desktop computer. Also, I cannot save my password in the mail preferences! It asks me if I want to save it and I say save and it is never there when I check. Keychain access does not work at all. I click add to keychain access but it never does, also, I enter my correct keychain access password and it says it is the wrong password. I simply do not know what to do. I tried emptying all the mail from the server but that did not help. I cannot understand why I only have the problem on my laptop altho it is intel. maybe that has something to do with it.
    does anyone have any help for the lack of saving my password? what is going on?
    thanks, Val
  67. 67Wayne Contello
    I think this has to do with:
    having multiple accountsI have three mail accounts ON THE SAME SERVER.

    The first one is always the one to fail (when there is a failure). I have now set my mail prefs as follows:
    + In the General section:
    – Check for new mail Manually
    + In the Accounts section
    – for each of my three accounts I have unchecked Include when automatically checking for new mail

    I think mail goofs up when the Check for new mail is set to Manually (which I have always had) AND the check box for Included when automatically checking for new mail is checked. So when checking manually accounts should not be included in automatic checks.

  68. 68Sharney Adams
    I too am having the same problem, it is slowly driving me insane, I love Apple, but I am at the point of switching to something else.My .Mac account and BT POP3 account work fine, but I have a company POP3 account which constantly asks for a password, it is saved in the accounts section and as a keychain, but it still asks for it.

    I have tried all the suggestions, a big thankyou for them but to no avail.

    I cant give any advice apart from leave it alone, it will make you go mad.

  69. 69Peter
    I have two Macs – one at work, and one at home.Both running the latest MacOSX etc..

    Both access the same mail account (amongst others). The accounts are configured identically.

    The one at home constantly asks me for the password – the other never has. Ive tried everything – but no luck.

    So unless its something REALLY wierd – like the Yahoo servers not liking my home ISP – then it HAS to be a Mac problem.

    The only think I havent tried is reinstalling Mail – but this is tricky I would imagine – especially if you need to make sure your got rid of all the old files, permissions etc..

  70. 70Mohammed Abdul Kareem
    One of the cause is that if the server is slow (POP3) then it cant accept lot of traffic and rejects the users who will get to it to communicatethe best solution is make the automatic send and receive for a long period so that the traffic generated is less and the server can respond to the clients one by one smoothly
  71. 71Bertie
    Reply 65 has sorted it for me. Thanks for the help Nick.
  72. 72Gardener
    This egregious Mail problem is hurting our business! We are experiencing this problem daily, and I find it difficult to beleive that the brilliant software engineers at Apple cannot improve Mails error reporting, and modify the Mail client to alleviate some of the failures.Because some of our users can sometimes get mail to work during peak hours, it may be related to the amount of mail you have sitting on the mail server (as measured in MB, not number of messages), as well as the degree of saturation of the (WAN) network, and how busy the mail server is. We can usually retreive our POP email during non-business hours (before 8AM, after 6PM) but during the day all of our accounts are getting the dreaded password failure.

    User rfca in message 55 above has hit the nail on the head. More detailed error messages would go a long way in helping us work with our ISPs to resolve the problem(s). Although it seems that changing the frequency of checking for new mail might help, I think its masking an underlying problem because it lightens the load on the server, which seems to be more likely to fail if the user has a large in-box. Sorry, I dont have a reliable workaround. Our ISP is stumped, too.

  73. 73Jerri Garretson
    Ive had this problem since March 28th on my iBook. I havent been able to get any mail through Mail since that date. Yet the SAME account settings and passwords work just fine using Mail on my desktop G4! And the same passwords work using the ISPs Webmail. So it clearly isnt the passwords or the settings, and its hard to see how it could be the ISP, since the desktop Mail program functions fine. Ive tried several of the fixes mentioned here with no success. Ive asked my ISP, but theyre stumped. Meanwhile, the only way to can get email on the iBook is through Webmail. Hardly satisfactory. I saw one other person commenting that mentioned the iBook connection. I use the iBook on wireless network that accesses the internet just fine . . . but could that have anything to do with the Mail problem (though it didnt before March 28th)?
  74. 74Peter
    I work for an ISP that has been banging its head on the wall about this, we finally found via logfiles macmail will atrempt a pop connection and if it gets no responce in a few seconds it will try POP which our servers do not do. It then asks for the password and will fail on it. A workaround that works for us is to set it to always use SSL. This works and knocks out about 90% of those keychain popups.How to setup SSL

    1. go to preferences in Mail,
    2. choose accounts
    3. click out going mail server settings button
    4. check off, Use Secure Sockets Layer SSLServer Port: 995
    5. select use password authentication
      6, close preferences, restart Mail
    6. click Get Mail and if it asks for the password/keychain again enter it one last time. (hopefully)
  75. 75Jacki Distad
    Heavenl father,
    Some nit-wod knows my password and have switched it. I have been living life the hard way for freekin long enough!!
    Might I add, this font is da bomb!!
    Going on, if you could just tell me m new password, then, I could put my crochetting down.j/k-just kidding!!

    -Jacquie Distad

  76. 76anne
    Thank You!! All the other thunderbird help forums were useless, which actually lead me to you, so good thing they dont know their own stuff. I appreciate your help and hard work finding this problem!!
  77. 77Peter
    If you have Yahoo accounts, then postings 65 & 74 will fix the issue. Well – they have for me – so far :-))I havent checked the Yahoo POP and SMTP settings for many months – and my Yahoo account page indicates these have now changed, and are using different ports and SSL.
  78. 78James
    Many thanks for the fix, Andrew. My was refusing to remember ANY passwords on reopening. Your hint above appears to have done the trick.
  79. 79Dave
    And I thought I was the only otherwise sane person who wants to show up on Apples campus and get arrested over this issue! Thanks for the support. Now, has EVERYONE here provided Apple with feedback (there are various ways, use all of them, including opening AppleCare tickets) on this issue?Error correction is used all over the place on our machines. Does Apple make us get out a calculator and do the arithmetic each time? No. So why doesnt Mail notice when we keep entering the same password and automate this for us?

    Answer 1. Because the Mail programmers are as dumb as Adirondack deer?

    Answer 2. Because people are taking the time to post here, but they ARENT hassling Apple over this with every resource at their disposal.

    Id go with Answer 2. Were all to blame, people!

  80. 80Robyn
    So, my issue is that my password wont save? This is new? I dont know why its not saving in the preferences? Could it be the same issue?
  81. 81Liyakath Ali
    Hi,Even though my login and password are correctly giving in my yahoo mail is giving the error as your login ID or Password invalid.
    Can you give me the solution for this as soon as possible.
  82. 82gail
    Dan, When I try opening Keychain Access (per your Update Solution, April 26, 06) it starts up Classic which I am no longer working in. Do you have a fix for OS10? This is driving me mad. Thanks so much.
  83. 83gail
    Ive got my problem FIGURED OUT! Aside from the Mac Mail program loosing its brain now and then and asking for the password, there was indeed an issue with the password with Yahoo. It seems that Yahoo has changed its requirements for passwords since the time I signed on. It now insists on 6 characters, 2 of them being numerals, and my original password was only letters. So, Ive changed my Yahoo password, and updated my Mac Mail with the same. It now works, with the now minor inconvenience of the Mac Mail request for the right password to which I just hit the Cancel button. Hope this helps. gail
  84. 84david
    it seems sometimes people get lucky with solving this problem & others not – so im not offering this as failsafe but i think its finally the thing that, after trying all sorts of keychain & other things, has worked for me. theres a discussion about it on the apple supprt site. basically you go: system preferences, network, show network port configurations, then just uncheck the ways you dont access the internet, putting the ways you do use in priority order from the top down. hope that makes sense & helps others. theres no way of knowing if finally my pop3 providor just managed to sort themselves out at the same time as i did this as id disabled auto-collect mail from that one for a couple months. but now it goes online every 5 mins and picks up as much junk mail as i can handle.. woo..
  85. 85Dave Fazio
    THANK YOU – This one was bothering me. Except my change to the instructions is to NOT replace the login.keychain file. I still got an authentication problem for my outgoing server, until I didnt replace the login.keychain with the one I moved to the desktop. Everything is working fine now, saving me from a total reinstall. THANKS!
  86. 86Dave Fazio
    THANK YOU – This one was bothering me. Except my change to the instructions is to NOT replace the login.keychain file. I still got an authentication problem for my outgoing server, until I didnt replace the login.keychain with the one I moved to the desktop. Everything is working fine now, saving me from a total reinstall. THANKS!
  87. 87rob
    OK everybody – listen up.This problem is to do with mail and the POP server. Its not mail. Its not the POP server. Its to do with the status of the server and how mail handles this during non-normal times. By non-normal I for the most part mean busy.

    Legitimate keychain issues will have the same symptoms but this has confused the issue – usually the problem goes away simply by hitting cancel and re-checking mail a few moments later, so for most people its not a keychain issue.

  88. 88Alec Smythe
    Ive been pulling my hair out for a couple of weeks over this. Driving me crazy. So far your fix seems to have worked for me. Thanks!
  89. 89Lauri
    Ive got 3 email accounts set up in Mail on my MacBook Pro. 2 days ago one of them refused to connect, saying the password was wrong. Ive tried all the ideas on this page but to no avail. It has to be a Mail related problem because I have exactly the same set-up on my Mac Mini (the same 3 accounts with the same passwords) and that connects to all three accounts without a problem. Ive had both Macs set up this way for months and this is the first time Ive encountered this problem. Any new ideas or solutions out there ?
  90. 90Mike
    I had this problem recently with Yahoo mail thru a PC. I set up a new (free) email account and whilst I can connect to other Yahoo Mail accounts via Outlook Express i cant get access to this one although I can log on via Yahoo Mail via IE7 without problem. Yahoo help says this is because youre not subscribed to the paid version mail-Plus. This of course is rubbish because my other email accounts with Yahoo work fine. They may be suggesting that Mail-Plus is on a different less busy server and therfore wont be a problem. Still scratching your head? – me too!
  91. 91digging4fyr
    THANK YOU!I cant believe that stinking F@##$&*ING password window is gone. The only way your solution could be better is if it indexed better for the error when typed in google search. Thank you so much! My window was popping inscessantly!

    Thought it was the iPhone and the awful Mail synching it has, but nevermind – thank you.

  92. 92Adam Silver
    FINALLY – I FIGURED OUT WHY THIS WAS HAPPENING TO ME..I use Apple Mail on my Mac and I have multiple email accounts with Yahoo Small Business (regular POP accounts). Thinking back, the problem only started occuring for me after I got my iPhone (which also was checking my email accounts). Yesterday I set my iPhone to check my email accounts manually instead of every 15 mins (as it was set to). Voila – the Apple Mail problem is now gone. Also – this morning – I was checking my email manually on the iPhone and a few minutes later when I got back to my desk the Apple Mail bug was back. So, I think I can conclusively state that when more than one mail client is checking in with the mail server then Apple Mail pukes. Who knows whether this is a bug with Apple Mail or the server but in any event – it seems that only one mail client can be active at any one time.
  93. 93Jaggi
    Thanks mate. Had the same problem for ages and your fix works a treat!
  94. 94Shauna
    My webmaster just changed its mail program today and all of a sudden I am having the disappearing password nightmare on Entourage. Over and over again. I dont use mail and I am on a Mac. But I am ready to explode. At this point I have been on the phone with the webhosting company and they are finally admitting the servers may be going in and out. (5 hours later) So now I am back to believing its a server problem not an Apple problem. We shall see over the next few days.
  95. 95Don
    Your solution did allow me to get my Gmail. However, it deleted all my keychain entries.Thanks.
  96. 96Seamaster
    Many, many thanks for posting this fix . . . this problem was been driving me nuts. I have three BTinternet email accounts (actually Yahoo mail under the hood) and, like Adam in #92, since I got an iPhone last Friday, have had these errors. I think Adams tip to set your iPhone to check for new mail manually when Mail on your desktop machine is running, and switch to automatic when away is also a good one.
  97. 97Thomas E Redd Jr
    None of these options worked for me. I have had a mac for a long time, and almost exclusively used Mail client for all my email accounts. I have never had this problem until last week I upgraded to 10.5 and now I get this problem with Mail repeatedly asking for my passwords every time i re-open Mail. It takes the password fine the first time it asks, but when I exit and open Mail again it asks for the damn password again. WTF happened with 10.5 that was working fine for me before from 10.3 through 10.4? WTF knows
  98. 98Thomas E Redd Jr
    oops, to clarify, I did a clean install instead of an upgrade. Maybe thats why I now have a problem
  99. 99joseph
    what do you sugest i do or how do i submit my password ,ive only been on net afew day,s wasn,t expectin to have any problems like this; very frustrating.
  100. 100Brian
    Seems like different problems. This solution seems to work for those that have the issue that people attribute to a server timeout. The issue where it doesnt save in the keychain is a different issue. Ive read using keychain first aid and some other things to resolve that. Thanks agin for this fix! ugh my comptuer feels brand new again! The repeated passwords was driving me nuts!
  101. 101APPLE SUCKS!
    Fricking fracking apple A-holes the problem is with apple, mail, lookupd, network configurations, KEYCHAIN is very buggy, and especially its lousy os x coders (more like pretenders).same fricking problem (among MANY others) has been occurring for more than 3 years another bug apple has failed to resolve. what arrogant incompetent @-holes highschool dropout-redmond rejects.

    it will occur again no matter which solution you think worked for you. its hit and miss, completely random and it never stays fixed

    as #55 rcfa wrote: The real problem is, that we don’t have proper error handling in the first place and thus don’t get a precise error message that reflects the actual reason of failure, if need be, including quoting the mail server’s error message.

    and a lot of it lies in the buggy unfixed problems in keychain access still full of bugs,problems more unfixed bugs more crappy apple failures more arrogant we dont give a sh*t because they dont give a flying flip if youve already got a mac , they only care about selling to the ones who dontwhat a bunch of frauds.

    and as #79 Dave wrote: We the people AREN’T hassling Apple over this with every resource at their disposal. . We’re all to blame, people!

    at the very least everyone should send bug reports (via safari pull-down) every time you encounter this OR ANY OTHER PRBOLEM. just paste it into the bug report window and choose wrong behavior. it doesnt have to have a website address.

  102. 102Michelle
    THANK YOU for an actual solution!!!!!!!!!!
    I have been suffering with this for almost a month and ready to chuck the apple out the window. Thanks again!
  103. 103jeff
    that solution DOES NOT work (for me)
  104. 104Michelle
    I spoke too soon it is doing it again not 2 hrs later!!!!!!!!!!! AUGH
  105. 105Johan
    Just right after we celebrated NYD, 1st of Jan 2008, at about 3am Ive my mail keep rejecting the password. Since then Ive tried every solution there is online, including getting my server admin to reset my password, to no avail.Ive installed Thunderbird and been trying it too, but it also seems to be having problems. No password rejection but it kinda just keep searching or trying to log in. Ive also tried it on my old G4 powerbook running Tiger and Mail rejects password too.

    I just tried your method, but it says The password is invalid , which obviously isnt true. I could log in from my webmail. ZZZZ. Extremely frustrating as this is my work email. Any more ideas?

  106. 106Mason
    Another year has passed and the problem continues. Ive tried everything here.
  107. 107GrandGizmo
    Can someone please tell me the proper procedure for setting up BLUEBOTTLE EMAIL in MAC OS X What are the ports that are good? I have tried everything! It is horrible that bluebottle does not have that procedure on their website. 🙁
  108. 108Sal Chicho
    Amazing ! Thanks for the solution to my mail keychain problem, Andrew. Im bookmarking your site.
  109. 109Mich
    okay, 4 days now and I have no business email. WHAT IS THE PROBLEM anyway? I tried Andrews solution, also Keychain first aid, also #74 and #74 and one other I cant remember.I have NO idea what to do next. I cannot receive emails and the server keeps rejecting the password. This email is through my domain and the host cannot even get into the C panel to change the password, is that is even the issue.

    Any ideas on what to do next? Sent a note to Apple Support. No answer yet. I dont expect Ill get a solution there either. I am sure I will have more luck with someone elses helpPLEASE

  110. 110joydivisionovengloves
    I had this problem yesterday and have just got off the phone with BT Broadband.The solution was simple in the end, apparently my incoming mail server and outgoing mail server were the same and both incorrect. I have now changed them by going to Mail – Preferences – Account information.

    I changed the incoming mail server to

    and the outgoing mail server (through server settings) to

    This has worked for me but I guess is only relevant to bt internet customers.

    PS. Apple support simply referred me to my internet provider.

  111. 111Ash
    My daughters iBook G4 started acting up about a month or so ago. I think it went wrong following a security update. Anyway, she has a BT Internet POP sub-account. My master acount on my iMac is fine, but hers just gets the password error. I tried Andrews fix, but no joy. I will try #110 & also checking use SSL. This is a very weird problem; I installed Thunderbird & it too returns this message! Webmail works OK. I suspect Keychain is the culprit. BTW: I deleted the BT acount & started again from scratch; only problem is I have deleted all my daughters email! I tried retrieving it as per one of the posts above, but to no avail. Any ideas??????
  112. 112Neil Shapiro
    Ok, this problems been around since 2006 and still no solution. This has been happening to me with one of my accounts for months; it had seemed to get a bit better, only prompting me once every day or two. But today, its happening CONSTANTLY. My mail may work for 5 minutes, but then it gets the password prompt. So I tried your solution Andrew, and unfortunately, it doesnt work :(I love apple mail, but this will drive me away as soon as I can find something better.
  113. 113Craig Davies
    I have read nearly every post and tried all the options. Ive cleaned up the keychains, changed how often Mail attempts to get mail, tried online options, and pretty much every possible suggestion. Unfortunately I am still having the same problem and it is infuriating. I cant believe the guys at Apple arent sorting this out, or at least passing the buck to whoever they consider responsible for the problem.I have not long come over from Entourage where I had exactly the same problem, so It is not necessarily the app. It could however be something to do with keychain or a more inherent Apple issue, which is concerning. I must say though, I have an iPhone and this problem was occurring prior to me having it, just to reassure anyone that the Jesus Phone was the issue.


  114. 114Tammy Rogers
    I, too, have had this infuriating problem for a long time and started to implement your fix but after deleting the passwords from Keychain Access, I went on to move the login.keychain file and cannot find it on my computer not in the spot mentioned (/User/username/Library/Keychains) or even when Ive done a search. Now my email doesnt work at all and Im not sure how to proceed. Im afraid to reinstall anything lest I lose al my email, etc. Any thoughts?
  115. 115Tammy Rogers
    Just an update to my previous note.My email is working again but I am getting that password prompt every few minutes so I have to leave my email shut down. Does anyone know if this problem is resolved with Leopard?
  116. 116Greg
    I have now eliminated this problem.After reading about so many fixes and how each ultimately failed, I only tried the tweaks that were less potentially damaging. THEN I FOUND WHAT SEEMS TO BE THE FIX.

    I download into Mail three accounts, including two Yahoo accounts. Someone mentioned earlier about the volume of e-mail that sits on ones webmail account that is being accessed and how it might take Mail a little too long to access reading the account because of this load. After changing e-mail passwords (another suggestion that didnt work), I realized that I had a huge amount of files sitting on the web-server that I had never actually look at or frankly, need (thanks, Time Machine!). I had kept them there just in case. Well, I deleted most of them off the web-mail site and now Mail no longer gives me the password rejectAT ALL!

    I also culled the volume of e-mails on Mail but that is fractional compared to what I unloaded in my Yahoo accounts.

    Please try this and see if it works for you. Then tell me if I found the solution, just another red herring or a solution that is only specific to my machine (because some have said the error message may cover a myriad of problems). Good luck!