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
    2015-07-15T21:23:58+00:00

    I can't say that this will fix the situation for everyone, or ever be an option for many. When I installed the preview, I kept my 2011 installation active. I would use them interchangeably. I started having issues with the password prompt a few minor versions ago (I think as others have mentioned 15.8 was the last one that worked). I've tried a bunch of things to fix this and none of them worked. Yesterday I took the atomic option. I AppZapped Outlook.app, and then removed everything in the Group Container folders. I emptied the trash (some items were still in use and couldn't be emptied). Restarted the machine, emptied the trash again to make it squeaky clean, and then I reinstalled just the Outlook installer. With AppZapping the Outlook.app there were some configuration files that has to be regenerated by Outlook 2011 when I restarted that, but everything worked fine. So far, Outlook 2016 hasn't asked me for a password all day, even through multiple reboots. Now ... I have all my "On My Computer" archived email in 2011, so I could blow away all the content in the Group Containers. Your mileage might vary. Will report back if this issues comes back. I'm guessing this is one of the reasons why MS is finding it so hard to find the issue. Not sure of their test scenarios but maybe they're not testing update upon update (actually I'm sure they are) but 'in the wild' with all our different accounts, environments, etc, it can be a nightmare to track down the issue.

    Good luck, hope this was of help to some of you.

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  2. Anonymous
    2015-07-14T22:15:04+00:00

    Thanks for posting the screenshots, I was also wondering if this was solely related to exchange or if had to do with the Keychain entry and it appears to be the latter.

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  3. Anonymous
    2015-07-14T12:55:14+00:00

    Some news-

    Moderators of the official Microsoft Office Blog say they are looking into this issue and testing authentication with Exchange Servers. See the thread here. Apparently posts between there and here are being read by Redmond.

    Seattle Expat

    Thanks a lot Seattle Expat. Atleast some one is watching it. I hope there will be a fix. I tried IMAP instead of Exchange for Office 365 and still the same. Looks like some one screwed up the OFFICE 365.

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  4. Anonymous
    2015-07-14T07:20:28+00:00

    Ok-

    I had the patience today to look at this a bit more today. When I first opened up Outlook for Mac (15.11.2), connections to my Exchange Server seemed to be working. When I opened the Keychain App, I found the appropriate entry and my password was stored as it should be:

    A few mins later, Outlook gave me one of it's "need password" prompts, and I checked the KeyChain entry again to see what had changed:

    As you can see, the password field is completely blank. Somehow this magically gets wiped out at random, periodic intervals. Obviously, if no password is stored, then Outlook will prompt the user again. Since Outlook is the only app with access to this key entry:

    What else could be wiping the passwords?

    Hope this helps.

    Seattle Expat

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  5. Anonymous
    2015-07-14T06:13:03+00:00

    Some news-

    Moderators of the official Microsoft Office Blog say they are looking into this issue and testing authentication with Exchange Servers. See the thread here. Apparently posts between there and here are being read by Redmond.

    Seattle Expat

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