Outlook for Mac Keeps Asking for Password of Office 365 Account

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Last Updated: Sep 23, 2020

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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.

105 thoughts on “Outlook for Mac Keeps Asking for Password of Office 365 Account”

  1. I am at my wit’s end with this. Running Catalina 10.15.6 (19G2021) and Outlook 365 Personal v.16.41 (20091302). I am NOT using an Exchange server. I have two accounts, one with my own domain name, the other from my ISP, both residing on the ISP’s server(s). Only the account with my domain name is prompting for password.

    Both scripts return an error. The other solutions have not worked, at least not for any decent time.

    Why is this STILL a problem after all these years??

    Reply
  2. Turned of keychain on my phone, entered the password 4-5 times on Mac and it works until I restart Mac/outlook. Repeat process and it works again, for now.

    Reply
  3. My problem is similar but different. The difference is password prompt comes on restart of the system and once the user enters the password it automatically creates a new profile in Outlook=>Preference=>Accounts. So now the issue is most of the users have multiple accounts added with the same name and I’d in their Outlook.

    Any idea on this?

    Reply
  4. ”’
    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.”
    ”’

    The solution above successfully solved my outlook problem. The symptom I encountered was, the pop-up window when starting the app (should be related to modern authentication) is always white and I cannot do anything on it.
    After running the script, there was no pop-up window when opening the outlook.
    Lucky to find this page. Thanks a lot for your help.

    Reply
  5. I have tried this solution but it didn’t work for me. But this one https://support.office.com/en-us/article/office-for-mac-repeatedly-requesting-keychain-access-ced5a09c-3099-47cb-9190-e961bf63e240
    worked fine. I’m sharing it here because might be useful for somebody else.

    Reply
  6. The weird thing is that only 2 users (MacBook an MacBook Pro) are having this problem, serval colleagues using Macs (Air and Pro with same Office for Mac version) are not having this problem.
    We cannot find any differences in software and/or settings.

    Adri.

    Reply
  7. Hi Michael,

    I have read your post about this annoying error.
    Using Outlook for Mac 2019 (V16.28) on a Mac with Mojave. The office uses Exchange, probably exchange 2013 but I am not sure.
    I have removed the Exchange and Office entries in the Mac keychain and followed al the other suggestions to fix this problem. But the error is still there.
    After re-entering the password, the error-message immediately appears again.

    Now I am trying the workarround with the suggested scripts.
    First I got some syntaxis errors, and with my limited knowledge off scripts I do not know how to handle these.
    Later the response was the auto discover could not be set to false.

    Do You have suggestions how top get the script working?

    Kind Regards. Adri

    Reply
  8. None of those solutions are working, if you want to use “Outlook anywhere” within a Microsoft Exchange account. The only workaround is, to use a VPN connection – means the Outlook works fine in the office, but no chance to use it outside without vpn.
    I was searching for a solution in the past 2-3 years and its simply not working with all solutions I found.

    Reply
  9. When you open Keychain Access, make sure you click on show invisible items. Then you can delete all items listed above in this thread

    Reply
  10. Kimberly, thank you so much. It worked! I set (sudo defaults write com.microsoft.Outlook MsoHttpv2Outlook_override -bool NO) from the Terminal window, restarted the Mac and had to enter the passwords once. Worked like a charm. By the way, I have the most recent update installed – Ver 16.16 (180812).

    Then, I went back to really test this out… I moved the setting back to YES… (sudo defaults write com.microsoft.Outlook MsoHttpv2Outlook_override -bool YES). Then I restarted the Mac, brought up the Outlook application. No problems. It is still working after some 30 min of trying this. So… I assume this is a “setting reset” of some kind that fixed it. I don’t have any other explanations as to why it has started working now.

    That said, it MUST be the Mso setting Kimberly spoke about. Thanks!

    Reply
  11. Thanks for this thread. Had the same Login credentials problem on my Office 365. Here’s what worked for me. On the Keychain Access menu with “login”, search for “Microsoft”. The latest login appears on the list. double click it. It has a sub-menu called “attributes” and “access control”. On “Access Control”, you need to click the “allow all applications to access this item. The other option being “confirm before allowing access”. close any office365 apps and reopen them again. Right now everything is working fine on my Mac on office 365 apps. If I encounter further grief on this on my next login, I’ll update you! Hope this works.

    Reply
  12. I’m grateful for this thread! The problem started happening this AM completely out of the blue – there were no software updates (OS High Sierra, Outlook 2011 v 14.7.7) Deleting Keychain items did not fix the problem, but the ‘sudo defaults write com.microsoft.Outlook MsoHttpv2Outlook_override -bool NO’ solution mentioned by Kimberly & James above did solve the problem. Thank you!

    Reply
  13. I ran into a similar problem — Outlook “spontaneously” not accepting my correct Apple/iCloud password after an Office 365 update. For security reasons, Apple now requires two-factor authentication *and* an app-specific password for third-party apps (like Outlook) that use one’s Apple ID. The app-specific password did the trick, and now all’s well. For details, see: https://support.apple.com/en-us/ht204397.

    Reply
  14. This is ridiculous. Nothing seems to work and I hate Microsoft for it. I’m even on the latest Fast Insider beta build as I write this: 16.15 (180530)

    Thankfully with a site like this, I’m hopeful we will have this issue resolved by ourselves.

    Reply
    • Looks like the most recent Fast Insider version 16.15 (180602) may have solved the issue… though I’m not sure if it’s due to the combination of setting the machine to the following command noted by the user Kimberly above (“sudo defaults write com.microsoft.Outlook MsoHttpv2Outlook_override -bool NO”)

      I’m going to set it back to YES and see what happens after a reboot. I’ll post back IF the issue pops back up.

      Reply
  15. I’m a sole user – and consequently my own IT department. I’ve had this same problem for a couple of months. I’m trying the usual end-user response:- find the “solutions” on sites like this, try the ones I understand (not many of them – I get scared), find that they don’t work, try them again, find they still don’t work, and eventually decide to put up with it in the vain hope that someone somewhere releases an update to something which makes it all go away. The only good outcome is that I now know all my complicated passwords off by heart.

    Reply
  16. We’ve had a premier ticket open with Microsoft for weeks regarding this issue. On 5/24, they asked us to have folks manually disable MsoHTTPv2 which worked. On 5/25, we got an email from the MS engineer working our ticket. I assume this was a global fix: “Our PG has decided to pull the MsoHTTPv2 feature via flighting meaning that users will not have the feature enabled when they restart outlook. We no longer need to run the command to disable it.

    Please ask users who are experiencing this issue to restart their outlook clients to see if the issue is now resolved”

    Reply
    • Can I ask what steps you took to disable MsoHTTPv2 in your testing? I would like to replicate that test to confirm that it is part of the issue here.

      Reply
      • Sure, from a terminal window:

        sudo defaults write com.microsoft.Outlook MsoHttpv2Outlook_override -bool NO

        They recommended restarting the mac afterwards.

        Reply
  17. We only had 1 person report this in our organization (Exchange 2010 on premise) but it was fixed when she upgraded to 16.13.1 (18052304). She was affected for a week or so since it appeared for her in 16.13.0 (Build 18051301)

    Reply
  18. The issue is related to High Sierra and Outlook 16.11+

    We are not seeing the issue with SierraOS.

    High Sierra seems to be the issue. We’re also facing issues with MacOS 10.13.x always renaming itself under sharing, i.e. “Laptop”, after reboot, “Laptop (1)” and so on. Called Apple and opened a support case and they just blamed the network which makes zero sense and kept pointing fingers at everyone but themselves which they seem to be good at.

    Reply
  19. Hi, we’re facing the same issue here.
    Mac OS High Sierra, Outlook 16.11 thru 16.13, Exchange 2010 on premises.
    Although I’m extremely grateful to have found this post, neither workaround worked 100% as the issue comes back.

    Downgrading to Outlook 15.37 solves the problem but don’t want to do that with end users just yet.

    Extremely annoying situation and it’s rather disapointing that Microsoft hasn’t addressed it yet.

    Reply
  20. Hello,
    I tried all your solutions, but it is still not working for me. We as well do have the Exchange on prem. installed and the newest version of Outlook for mac 16.14., but the script you posted does not work for me and I’m getting the following error message:
    „Microsoft Outlook“ received an error: „exchange account “your-mail-adress”“ cannot be set to „false“.
    Any further ideas?

    Reply
    • Hi Christoph,

      Try the name instead of the e-mailaddress. That did the trick for me. It didn’t solve the problem, but it made the script work.

      Reply
      • Hi,
        yes the script is working as long, as I am logged in to our company network, or the client vpn is running – but sadly not within outlook anywhere and in our environment we only do have this issue when the client tries to connect the server through outlook anywhere.

        Reply
  21. I’m posting this possible solution here as this post has provided more info than the MS support site. I tried all of the solutions posted here, removed accounts, re-added, etc… I’m running OS 10.13.3 and Outlook 16.13.

    1) quit all MS products
    2) launch Outlook
    3) When it asks you for an account password, click “cancel”
    4) Go Tools->Accounts and enter your password
    5) Keep the Accounts window open (!!!)
    6) Go back to main window (cmd+1) [keep accounts window open!]
    7) Click on the tilde symbol next your mailbox that indicates the account is offline
    8) In the pop-up window, enter your password, check the “save password” checkbox, and click “OK”
    9) Close the accounts window
    10) Quit Outlook and relaunch

    Hope this works for others……

    Reply
  22. 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 :-)

    Reply
  23. 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.

    Reply
  24. 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.

    Reply
  25. 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.

    Reply
  26. 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.

    Reply
    • 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,

      Reply
  27. 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.”

    Reply
  28. 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!

    Reply
  29. @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.

    Reply
  30. 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.

    Reply
  31. 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. :(

    Reply
  32. 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.

    Reply
  33. 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!!

    Reply
  34. 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

    Reply
  35. 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?

    Reply
  36. 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!

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

    Reply
    • 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.

      Reply
  38. 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!

    Reply
  39. 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?

    Reply
    • 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”.

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

    Reply
  41. 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.

    Reply
  42. 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!

    Reply
  43. 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!

    Reply
  44. 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!

    Reply
  45. 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

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

    Reply
  47. I deleted my profile and created a new one – it worked.

    https://support.office.com/en-us/article/Manage-profiles-in-Outlook-2016-for-Mac-fed2a955-74df-4a24-bef6-78a426958c4c?ui=en-US&rs=en-US&ad=US

    Reply
  48. 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?!!

    Reply
  49. 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.

    Reply
    • 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.

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

      Reply
      • 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.

        Reply
  50. 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.

    Reply
    • 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.

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

        Reply
        • 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”

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

  51. 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.

    Reply
    • 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.

      Reply
      • 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.

        Reply
    • 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.

      Reply
      • 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.

        Reply
  52. 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] Web login required..” Your username/password or security settings may be incorrect. Would you like to try re-entering your password?

    Reply
    • Hi Kenneth, unfortunately I have no experience with Outlook 2011 or Gmail. But given the age of Outlook, I’d give the latest version of Outlook a shot.

      Reply
  53. 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

    Reply
    • 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

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

    Reply
    • 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

      Reply

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