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Outlook for Mac keeps asking for password of Office 365 account

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Many users have reported that Microsoft Outlook for Mac keeps asking for the password of their Office 365 account. Thanks to readers of my blog, we have finally fixed the issue for most users. For others, we have at least a temporary workaround until Microsoft provides a fix.

Outlook: Mail could not be received at this time

Like so many other users, I have experienced this problem in combination with my company’s Office 365-hosted Exchange account. Microsoft Outlook 2016 for Mac would randomly but repeatedly prompt me to enter my username and password. The exact error message reads:

Mail could not be received at this time: The server for the account [account] returned the error “Logon failure: unknown user name or bad password.” Your username/password or security settings may be incorrect. Would you like to try re-entering your password?

Outlook for Mac keeps asking for password of Office 365 account

Mail could not be received at this time

Outlook for Mac keeps asking for password of Office 365 account

Enter your account information

Re-entering the credentials makes the dialog temporarily disappears. Sometimes for a couple of hours and sometimes for a few days. But it always reappeared!

Likely cause: Office 365 modern authentication

I suspect that the issue is related to changes in the authentication mechanism that Microsoft introduced in one of the early version of Outlook 2016.

Outlook for Mac keeps asking for password of Office 365 account

What’s new: Issues are likely related to some of the new features

Microsoft fixed the problem with one of the Outlook updates, but unfortunately, the update did not delete individual Keychain entries. Without removing those entries, the problem keeps reappearing. I had tried deleting some entries but missed a few until one of my readers of this blog provided a complete list of entries you need to delete.

Outlook for Mac keeps asking for password of Office 365 account

Exchange account credentials in Keychain

How to fix the problem (for most users)

Launch the Keychain tool and remove the following Keychain entries:

  • Exchange
  • Microsoft Office Identities…
  • MSOpenTech.*
  • Some “OC” keychain entry that might be unrelated

Thanks to Andy R for providing the solution!

Temporary workaround (for everyone else)

If the above solution did not fix your problem, you might have to disable “autodiscovery” using Apple Script temporarily. To do that, perform the following steps, as pointed out by readers YMX and ITadmin:

  1. Go to Spotlight Search > type Script Editor in the search box
  2. Open Script Editor and enter the commands below
  3. Run this script by clicking on the play icon or by going to Script > Run.
  4. Now start working in Outlook and verify if you get the password prompt for the Exchange account in question.

Depending on the exact version of Microsoft Outlook you are using, you may have to try two different “set background autodiscover” commands;

Option 1

tell application “Microsoft Outlook”
set background autodiscover of exchange account “your email address” to false
end tell

Option 2

tell application “Microsoft Outlook”
set background autodiscover of exchange account 1 to false
end tell

To reenable “autodiscover” run the above command again but use “true” instead of “false.”

Outlook for Mac keeps asking for the password

Sometimes a minor gap in quality control, such as the lack of proper upgrade testing can have annoying consequences. The problem “Microsoft Outlook 2016 for Mac keeps asking for password” has been around for since March of 2016. Microsoft should have addressed this issue a long time ago with a patch. At least, they should have told users how to fix the problem manually.

About the Author Michael Kummer

I was born and raised in Austria. I speak German, English, and Spanish. Since moving to the U.S., I have lived and worked in the greater Atlanta area. In my twenties, I was a professional 100m sprinter. These days I do mostly CrossFit. I'm a technologist and Apple fan. I love science and don't believe anything unless there is proof. I follow a Ketogenic Paleo diet and intermittently fast every day. I'm married and have two trilingual kids. My goal with this blog is to share what I learn so that you can spend time on something else. Check out my latest Diet, Fitness, and Technology articles.

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  • Jon Dagle says:

    Same problem occurs on Mac with Google/Gmail credentials. One such discussion here:
    https://discussions.apple.com/thread/6555756?tstart=0

    • Stuart says:

      PI have been struggling with the same problem for days not and stumbled onto a fix that worked for me..and so simple.
      Log into your Gmail account on a web server and go to accounts .. security, and look for the box that says allow access to less secure apps. Tick it and you’re set

  • Graham Caulfield says:

    Hi Michael

    RE: Workarounds: If the two issues above really annoy you, like they do me, the best workaround is to downgrade Outlook for Mac to Build 15.19.

    I would be very careful about doing that. I did it under the instructions of an Office 365 Help Desk associate. It didn’t fix the problem, but it did create a day’s extra work for me. When ver. 19 was downloaded and opened – it downloaded 2000+ emails I had already received on ver. 20. And the Office 365 “engineer” had me repeat the process several times because Outlook 19 did not retain my Password either. After a couple of hours on the line with him I decided he had NO idea of how to REALLY fix the issue and decided to work it out myself.

    He told me to leave Ver 20 there and just rename it for the time being. DON’T LEAVE IT THERE if you are going to use Ver 19.

    After cleaning up all my duplicate emails, and while using ver 19, I was working on a Word document and decided to email it direct from Word Ver 20 by using File, Share, HTML etc. Guess what, Outlook ver 20 opened up, and before I noticed, it had downloaded another 2000 emails.

    I have since deleted ver 19 as it cannot handle the formatting and font sizes etc. of email templates I created using ver 20. I am back on Outlook 20 and have decided it is safer to just enter my password whenever it asks for it.

    regards
    Graham

    • Hi Graham!

      Thanks for the info! The downgrade worked smoothly for me. I just renamed the old application and installed the new one. My mailbox was fortunately unaffected and the error went away. That being said, the font size of my signatures gets messed up with every up/downgrade of Outlook.

      Given all the issues, I meanwhile switched to Apple Mail to handle my work emails. Only on iOS I still use Outlook to separate personal and work emails.

      Cheers
      Michael

  • KENNETH WHITE says:

    Please can you help me.
    From reading your forum – seem to be the only sensible sounding person.
    Mac turned on – Outlook 2011 keeps prompting password – over and over and over – but unlike some of the other forum users, it is NOT connecting. iMap with Gmail.
    Keeps saying “Not connected with Gmail”

    The server for account “Gmail” returned the error “[WEBALERT https://accounts.google.com/signin/continue?sarp=1&scc=1&plt=AKgnsbtybq_5d9LIliNn_ukEx7iqeenfSzMI6XqpmnNW2I0BgRUgJedUf82mWqJxvi3qvkVNoA1k4HIu1PEs75EP3nkV0qpocPXaadsGftH1lr0u96JJqpGs8QxCMfNZMJ0AhDjd4DBT0QHgWtn_ElLctDOt5RxE0g3OxSRefg-2LZ2Ou9XQLGqHJcEm5oI8Ih1t6TmwMUMwxBaENwAG4wpLB0lP9Jgf44p0B-lK_Iwg6d5i5GXbzQ0%5D Web login required..” Your username/password or security settings may be incorrect. Would you like to try re-entering your password?

  • C P says:

    Running 15.23 and the username password re-prompt issue remains. MACOS is El Cap.

    • Do you use an Office365 account? I switched back to Apple Mail because I was fed up with all those issues in Outlook but a co-worker who still uses Outlook tell me that while Outlook is running he doesn’t get prompted. Once he closes and restarts Outlook he gets prompted, but only once.

    • Tami says:

      Hi, Cp.
      Why you are getting this issue is cause you have to upgrade you Mac to High Sierra.

      • Marie D Kratsios says:

        Hi Tami. I am also having this problem, but I am running High Sierra. It’s all very annoying. I seem to be getting messages, but emails I am sending out are stuck in my Outbox.

  • Hi Michael
    I’m running Outlook Version 15.23 and I am having same issues, only more often. I have an Office365 account (Business Premium). I am running Airmail 3 and Mail concurrently as well in an attempt to get to the bottom of what is going on. I also access the same mail through Outlook,com on my iPhone 6s – but NEVER prompted for login details. I have also setup Outlook.com on my Macbook to observe. But as I learn more advanced tools with Apple Mail I am going to transition. Just had enough of this Outlook issue. Seems to go back several years.

    • Have you tried signing up for the beta program? I’m part of it but haven’t tested Outlook since my transition back to Apple Mail.

      • Graham Caulfield says:

        Yep. Signed up already. Not sure if that’s a good thing or not. Seems every version creates as many problems as it saves.
        Do appreciate the ability to finally be able to customize the ribbon etc. in Word.

  • Ben A says:

    Glad to see I’m not the only person with this problem. I recently switched to Outlook 356 for Mac and I keep getting the password request. My problem is worse in that Outlook keeps sending the incorrect password (or no password) and my corporate Exchange server locks me out of my account. At least I know I’m not the only one with the issue now. Time to see just how good Microsoft support is.

    • MelodyM says:

      Just started having this issue recently (in 2018) and it’s driving my VP of sales insane. Bunch of macs on our system but only affects 1 or 2 users. About to dump office Outlook and go back to apple mail.

      • Maurice says:

        Same here since yesterday (May 2 2018..) so something must have triggered this! It is driving me crazy too….

        • Hoerbie says:

          Same here since May 3, but only at some Macs, not all.
          I didn’t find lots of the listed entries in the key chain, and the script thing doesn’t work, only says (translated from german) “microsoft outlook got an error: “exchange account “[email protected]”” couldn’t be set to false”

          • Daniel Katz says:

            Likewise. Started in the April edition of Outlook for Mac on some of my users. If we revert to February, it works fine.

          • Maurice says:

            @daniel Katz: How can I revert to a previous release of outlook (Mac)

  • Howdy

    I had the problem for the last several months and called Office 365 support on several occasions, coming to the conclusion they didn’t have a clue how to fix it. I was getting the enter password prompt about 30-40 times a day.

    Yesterday I called again and actually got an agent who knew how to fix it. It is now over 24 hours without the issue occurring; and I have been in and out of Outlook multiple times without an issue.

    The fix only involved exiting Outlook, deleting all Microsoft entries in Keychain, and re-opening Outlook.
    NO deleting/renaming/reinstalling Outlook (been down that road before).

    That was all we did, and so far so good.

    • Make sure you upgrade to the latest version of Outlook before. I tried this with an old build it didn’t work because Outlook kept messing up the keychain entries that store the password. It seems like newer versions don’t do that anymore.

    • Ben A says:

      I got the same response. Go into Keychain, deleted the Microsoft entries, and restarted again. So far it hasn’t occurred again.

      • Ben A says:

        Aaaaaaand it came back after about a week. My solution was to stop using Outlook and use Airmail instead. 70% of the functionality, but I don’t get locked out of my corporate email because Microsoft can’t figure out password authentication.

  • Dude says:

    Go into Keychain, deleted the Microsoft entries, and restarted again, fixed it for me.

  • koi says:

    Couldn;t find a fix on the www so went back to Outlook 2011 which is working just fine.

  • Alex says:

    running version 15.27 deleting key chain entries did not owrk

  • Scott says:

    Best solution: Just delete and install the latest version of Outlook. It worked for me. (I have Windows 10)

  • Benjamin says:

    Im also running version 15.27 deleting key chain entries did not work either.

  • B. Baldwin says:

    I have the same problem, and I am getting the annoying pop-up password request several times a minute, making any work impossible. How on earth can MS have the cheek to ask 70 pounds a year to subscribe to MS Office when it is incapable of fixing such an elementary fault in its software that has such a debilitating effect on productivity and one’s patience?!!

  • Sailesh Singh says:

    Just ran outlook update from Help menu and all works fine now.

  • Jean Simon says:

    I just exited Outlook, deleted all of the Microsoft entries in Keychain and re-opening Outlook. It is finally fixed!

  • Andy R says:

    I had the same problem with Outlook 15.30, running on MacOS 10.12.2. (I do not know if this is Sierra-related or not.)

    I changed my corporate password, which is integrated into Outlook 365. Mac Outlook kept re-prompting me for my password. (Android Outlook worked fine.)

    Every time I was prompted for my password, I’d see a lot of movement in the Keychain Access app in the m’s. This implied that Outlook could not write to its own keychain entries.

    To fix this, I had to delete a lot of keychain entries:
    – Exchange
    – Microsoft Office Identities…
    – MSOpenTech.*
    – Some “OC” keychain entry that might be unrelated

  • PhillipS says:

    I followed Andy’s route and deleted the MS and exchange entries including the Bundleseedid (Outlook).
    Followed this with a restart and entered the password when requested.
    Problem fixed.
    Thank you everybody!

  • Phillip S says:

    I followed Andy’s route and deleted the MS and exchange entries including the Bundleseedid (Outlook).
    Followed this with a restart and entered the password when requested.
    Problem fixed.
    Thank you everybody!

  • Phillip S says:

    I followed Andy’s work around and deleted the MS and exchange entries including the Bundleseedid (Outlook).
    Followed this with a restart and entered the password when requested.
    Problem fixed.
    Thank you everybody!

  • Carsten O says:

    Thanks to Andy R – deleting the Exchange*, Microsoft Office Identities* and MSOpenTech* entries fixed the issue. It wasn’t the first time I had this annoying problem… Now (as I think about) it occurred last time, after I had changed my O365 password.

  • MSLover says:

    Deleting the Keychain entries only temporarily fixes the issue. I tried it, no prompts – for awhile, but next day the same prompts again.

  • tim says:

    I went in to key chain and dont have any of the above stored? Am I looking in the wrong place, i.e. Is it in one of the sub options in key chain?

    • Hi Tim!

      It seems like Microsoft may have renamed or dropped some of these entries. Just select the “login” keychain and “All Items” and search and delete “Microsoft”, “Exchange”, and “Outlook”.

  • silvio says:

    After trying with no success all recommended actions (cancelling all keychain keys), I WAS FINALLY ABLE TO FIX THE ISSUE!!!

    my email is [email protected] and by using these credentials I had reported issue.

    as my old company credentials were “name_surname”, I inserted [email protected] (which is NOT my email address) and usual password.

    Issue fixed!

  • Chiadi says:

    This annoying issues still persists with the just released 16.9.0… hosted Exchange account. There will be no fix.

    • CW says:

      running to this issue with one of the users at my company. I deleted keychain entries that contain anything outlook, microsoft, exchange, as well as deleting the outlook account and recreated. Though I am reluctant to uninstall/reinstall Office, I doubt it will resolve the issue. There must be some recent update(s) causing the keychain and Outlook to break. BTW, user has the latest Office update installed.

  • soltkr says:

    Had a client whose Mac outlook 2016 app was repeatedly prompting for password after we enabled two factor authentication for their tenancy. Removing the keychain entries listed in this post was the answer. thanks for the info!

  • TP says:

    I did a recent Microsoft update on my Mac 2016 and Outlook constantly prompts to enter in password every 5 seconds. I went into Keychain entrees to delete Exchange (that is the only one I found in my keychain from the suggested list ) however, it will NOT delete. I tried deleting , restarting my computer to see it would have helped . Nothing. Any suggestions?

  • IK says:

    As usual. It’s Microsoft. Can I expect any less. Headaches, troubles all round their products and this is no exception. Exchange is a nightmare. Only reason i use it is because my organisation uses it as primary email. Am having this problem too. All i did was change my password and then boom. every time i launch it, it asks for username and password every singly time i open outlook

  • jimmy says:

    It is *Still not fixed as of last update. I cannot take a client’s outlook beyond 16.9 or password prompt hell… also prevents updating of the entire suite, which is bug-ridden. Freaking nightmare. Hosted Exchange. Absolutely AMAZING this is not fixed, now 4/2018!!

    • cw says:

      same here..as of 4/27/2018, issue is not fixed. Now, we are getting reports from more users with exact problem.

  • ChiefSlapaho says:

    I completed removed everything from the affected machines. Deleted all Office applications, deleted all cached and leftover files under Group Containers, keychain items, etc.

    Nothing did it. What ended up working (so far) on both machines that were exhibiting the issue, was to reset the keychain manager forcing the user to re-enter all application passwords that they were prompted.

  • jimmy says:

    What do you mean “reset the keychain manager forcing the user…”
    The utility is Keychain Access and it has no master “reset”.
    Just curious. But there is no fix and one is not coming. :(

  • jimmy says:

    Thanks.
    Has this “fix” been confirmed by others?

  • Daniel says:

    I have found that by reverting to Outlook version 16.11 resolves the password prompt issue. Nothing with Keychain or passwords made any difference.
    Having tested Outlook version 16.12, 16.13 & 16.14, I can confirm all 3 of these versions result in multiple password prompts.
    It looks like the recently introduced Autodiscover mechanism is the cause of the issue and may give different results based on who your Exchange supplier is.

  • Dayon says:

    @Daniel, we might be trying this soon where I work. Have already tried everything else with no luck.

    I’ll be sure to post on here if this fixes our issue for others on this chain to see.

  • YMX says:

    I began having this issue yesterday for no apparent reason. I was using build 16.12 and just tried reverting to 16.11. Still same issue. We use Rackspace Exchange Hosting, they have not been able to solve the issue. Anxious for any answers!

  • YMX says:

    I just chatted with MS support through the Contact Support area of the Outlook help menu. They were quick to respond and told me that it is a confirmed bug:

    “Thank you for all the information provided. Please be informed that, we were able to identify this issue as a bug and have reported this bug to the ‘Product Team’ to investigate further. Currently, the ETA is unknown, I would request to keep Outlook updated to avail the fix once it’s available.”

  • Counterdoc says:

    We have the same problem since yesterday. We are using Exchange 2016 + Outlook for Mac 16.12 and tried all these keychain-fixes, but no luck. Users are re-entering the password and it keeps the prompt away for 5-10 minutes. I told them to use OWA the next days/weeks until there is a fix.

    @YMX: Would be great if you could keep us updated for any response of Microsoft.

    • Uf M says:

      Hey,

      we´re having the same issue in out company. Exchange 2013 and Outlook for Mac 16.12.

      The only Workaround is to downgrad to 16.11

      This will fix the problem…Hope it is fixed in 16.13

      Kind regards,

  • YMX says:

    Good news. I was able to get to a senior Microsoft Mac team support specialist directly through the Outlook “Contact Support” feature.
    They were able to temporarily solve the problem by having me use Script Editor to turn off Autodiscover. However, they said it is not a good idea to leave this permanently disabled and said it was an issue that you need to fix on the hosted Exchange side.

    Here are their exact instructions:

    “Let’s disable background autodiscover for your account by running the following script. After this, work on Outlook for a while and verify if you still get the password prompt.

    1) Go to Spotlight Search > type Script Editor in the search box.

    2) Open Script Editor and enter the following command:

    tell application “Microsoft Outlook”
    set background autodiscover of exchange account “your email address” to false
    end tell

    3) Run this script by clicking on the play icon or by going to Script > Run.

    4) Now start working in Outlook and verify if you get the password prompt for the Exchange account in question.

    Note: It is not recommended to leave the autodiscover feature disabled. After testing, ensure to enable it by running the following script:

    tell application “Microsoft Outlook”
    set background autodiscover of exchange account “your email address” to true
    end tell

    Thanks for your co-operation. Please keep me posted on the status

    I let them know that Step 2 fixed the problem, and Step 4 made it come back. So I reran step 2 and turned off Autodiscover for good.

    They then said:

    Awesome!! I am indeed glad to hear that. Now, this shows us that the auto discover isn’t setup correctly on the tenant for your mailbox. Hence, at this point of time, I would suggest you to talk to your IT Admin and seek help from them to setup the auto discover correctly and that should fix this for you

    Just let them know the test that we ran here and they should be able to get this fixed through their Exchange server team.

    This doesn’t depend on the server version but depends on the mailbox in the tenant, that is the reason this isn’t working for you alone.

  • NPB says:

    Hello YMX, that procedure doesn’t at all prove there is an issue with the exchange server’s autodiscover (the agent is just pawning it off on someone else cause they are unable to resolve it. It only suggests that the issue is in fact related in some way to the autodiscover mechanism and the way it communicates the password to the server. This issue is not present on Windows computers and actually was present a few weeks back on Windows computers and turned out to be Microsoft forcing Outlook to autodiscover their 0365 servers and try to connect to them and since the instead of the non 365 hosted exchange servers. This is very likely a similar issue if not the exact same issue, which was eventually resolved by Microsoft with an update to their Office suite.

  • ITadmin says:

    After about 14 hours of knock-down drag-out conversations with O365, Apple and our Exchange provider’s support being unable to fix this problem, I found this article. I asked the O365 support rep to implement the “temporary workaround” listed on this article, and it fixed the problem of constantly being prompted for credentials.

    However, the script had to be slightly modified for it to work in our case. The below 3 lines are the script lines that ultimately were the successful workaround for us. We’re on Outlook 16.13 on High Sierra, in a hosted Exchange 2013 environment (not Exchange Online).

    tell application “Microsoft Outlook”
    set background autodiscover of exchange account 1 to false
    end tell

    There may be consequences to this workaround that we aren’t aware of yet, but it lets us get back to work.

  • ITn00b says:

    Hello, just wanted to let you know, that deleting keys in the keystore did not work for me in MANY Outlook revisions.

    For me it was the ‘set background autodiscover…’ that did the trick. Both using domain login credentials and login witk email address.

    Outlook v.16.14 (180516)

    Thanks :-)

  • MikeM says: