Outlook for Mac 2016 - Repeated password prompts still an issue ...

Anonymous
2015-06-20T22:09:21+00:00

All-

As we know, one of the biggest bugs in Outlook for Mac 2016 is the ever-so-annoying repeated password prompt problem. This refers to the constant pop-ups that make it appear like Outlook is forgetting your password every few minutes, etc. The problem was much discussed during the Preview phase of Office for Mac 2016 but never corrected. I did some digging on the forums here and found other threads that covered this problem with slight variances, but the core issue is the same -- credentials are somehow not being stored properly or become corrupted during normal operation of the software. List of the relevant threads I found below. This list may not be comprehensive:

It seems odd that a major bug like this remained unresolved after the official release of Office for Mac 2016 ... and still hasn't been corrected! Per post responses on Microsoft's official Office Blog, they are looking into authentication issues with Exchange Server, but who knows what that means or how long that will take. Based on what I can gather:

  • Bug shows up in Outlook for Mac versions 15.9.x and up, therefore ...
  • Version 15.8 and earlier are not affected, but that is a super old preview version from 2015
  • Changing the way you present your credentials can sometimes help:

            e.g. username@DOMAIN vs. DOMAIN\username vs. username

  • Problems seem to affect Exchange Server authentication as well as IMAP or POP,
  • Deleting your account and setting up Outlook from scratch sometimes helps,
  • The issue seems to be intermittent, comes and goes.

A ticket submitted by forum member *Filip Herman* to Microsoft's technical support around early August 2015 indicated that Microsoft is aware of the problem and has a planned fix in progress. Obviously its been years since that. Others have submitted tickets to support since. Scroll to the end to read the most current progress.

I'd encourage everyone to mark this post, indicating that you "recommend this discussion." This thread has tens of thousands of views and hundreds of comments, so its clearly not an isolated issue. Unfortunately, my company abandoned the use of Outlook for Mac 2016 some while back because of this issue, so I don't have an active platform to test on anymore. However, keep trading ideas here as needed.

Best of luck-

Seattle_Expat

Outlook | MacOS | Legacy Outlook for Mac | For business

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  1. Anonymous
    2015-07-30T14:29:04+00:00

    Short luck... I got fewer prompt but still prompts. I soon give up :-(

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  2. Anonymous
    2015-07-30T14:23:02+00:00

    Hmm, i just tried this with some success on 15.12.3

    In Outlook Account i entered :

    Username: DOMAIN\Username

    Password: <mypassword>

    When Outlook start it soon prompt for password, username is picked up correctly as entered in Accunts. I enter password, select "Remember to keychain". Outlook connects nicely to Exchange.

    Before when Account was just using Username, I could easily stress a password prompt by clicking around on different e-mail and switch to calendar back and forth. Now it is steady, only prompt for password at startup. 

    Now I just want to get rid of the startup-prompt ;-)

    I give it some time to see if it is pure luck...

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  3. Anonymous
    2015-07-29T23:52:01+00:00

    I am not sure it is a keychain issue now...I shut down Outlook (quit) and then removed all entries in my password keychain that included my userID and Outlook/EWS etc. Restarted Mac then opened Outlook. It prompted for my password which I entered but did not check the "use keychain" checkbox.

    Checked my keychain and there was no new entry (so far so good).

    After about 10 min. Outlook again prompted for my password. I entered it but did not select the use keychain.

    Checked my keychain and there was no new entry. Outlook continues to prompt for password, it appears whenever it checks for new mail.

    *sigh*...so probably not the keychain...there must be something else in one of the many configuration files I guess.

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  4. Anonymous
    2015-07-29T21:31:29+00:00

    Everything was working fine for me prior to 15.12.3...I had never had this password prompting issue and was very happy...then came 15.12.3 and now it is unusable.

    Interesting that in the keychain it showed my account as <userid>@ews.<domain> which is not the format we use so I changed it to <AD>&lt;userID> and that seemed to work briefly...when I got prompted again, it created a new entry in the keychain of the <userid>@<domain> format. If I deleted that new entry while Outlook was running it seemed to reduce the prompts.

    Still hasn't really fixed it but it does seem a problem with the keychain and Outlook. Maybe there is an other key that is corrupt or something?

    Anyway, fed up and will just use Windows based Outlook through VM until MSFT fix this issue...

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  5. Anonymous
    2015-07-29T20:04:05+00:00

    Thanks Stu.

    I am currently traveling at the moment (vacation) so I won't have the updated Outlook for Mac in front of me for a couple more weeks. But I will be reading the feedback here until I get back. I'll see if I can mirror your experiment here. Thanks for posting your results.

    Cheers-

    SeattleExpat

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