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
    2015-08-12T16:01:16+00:00

    It has fixed it for me.

    No more password requests (it was driving me to despair).

    No more crashes.

    So I am back to where I was several versions ago, with a copy of OUTLOOK that is actually usable. At long last. 

    I'm not sure I can notice an positive improvements from the upgrade, but I'm so relieved to be back at "usable" who cares?

    It does seem to be something more complex: why some people suffer, others don't;  why the patch fixed it for me but not others

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  2. Anonymous
    2015-08-12T19:46:50+00:00

    So, very strange for me. I updated to 15.13.1 and now when I launch Outlook it says "Not Connected" at the bottom, but I am still receiving and sending emails with no problem... I tried deleting all outlook keychain entries, and the same thing, it takes my username and password but says "Not Connected" at the bottom, but seems to be working fine.

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  3. Anonymous
    2015-08-12T20:17:22+00:00

    For now this fixed my problem but I did do one thing before running the 15.13.1 update.

    • I removed the entries in keychain referencing our "Exchange" server (there were two)
    • I applied the update
    • I put in my credentials (username only) and password.
    • I did NOT check save in keychain.
    • The Account preferences have not wiped out the credentials after a shutdown and restart, quitting and restarting Outlook about 6 times over the last 12-16 hours.
    • I now have one keychain entry now, not two.

    So far, so good for this guy, let's see if I can make it through the week.

    -Stu

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  4. Anonymous
    2015-08-12T20:55:15+00:00

    Stu - you may be on to something here.  

    I followed your procedure, but I was still being asked for passwords.  I added a couple more steps, and everything appears to be working.  Here's my sequence:

    • I removed ALL entries in keychain referencing any "Exchange" server (I found four since I was using Outlook 2011)
    • I applied the update (i.e., I ran Outlook 15.13.1)
    • I DELETED my existing exchange account
    • I RE-ADDED my exchange account
    • I put in my credentials (username only) and password DURING the ADD ACCOUNT process.
    • I did NOT check save in keychain.

    So far, so good.

    Good luck, and thank you!

    Bill

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  5. Anonymous
    2015-08-12T21:37:45+00:00

    Hey guys,

    Are you removing just the "Exchange entries" which tie to your account or are you removing anything that has "Exchange" in it such as Private exchange key/Public exchange key etc..

    I've included a screenshot of what I've been removing within the Keychain.

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