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
    2016-07-17T14:50:21+00:00

    Why would he do that if the issue still exists on the latest version? We're not having issues updating, we choose use an old version because they actually work.

    --

    I've actually found that 15.19.1 works great - no errors whatsoever. I tried the Insider Fast branch (15.25) and the issue is present on that. Looks like I'll be staying on 15.19.1 for a while...the constant Autoupdate prompt is annoying though.

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  2. Jim G 134K Reputation points MVP
    2016-07-17T14:28:40+00:00

    15.17 is considerably out of date.

    The first thing to do is install the recent updates. Make sure your Mac has a working internet connection, then:

    Update Mac OS X. Open the App store and click on the Updates button. Install the updates.

    After, in any Office application go to the Help menu and choose Check for Updates to launch the AutoUpdate app. Let AutoUpdate install updates and then restart your Mac.

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  3. Anonymous
    2016-07-12T14:45:33+00:00

    Same issue here for every single update after 15.17. I went as far as to restore my Macbook back to April 2016 before this ever happened, HOPING that was the issue. Nope; still happens.

    Recently when I VPN into my work environment I get the typical random authentication pop-up, only this time it will NOT accept it and immediately locks me out of every application associated with my AD account, even attempting to connect to Outlook webmail without VPN. After multiple calls to my corporate help desk, they persisted that I was not locked out. So I just decided to wait it out. Sure enough, after 15 minutes I am good again. This has been going on every day, all day, randomly, causing me to lose a lot of productivity. Oddly this only happens with VPN. Otherwise it is just the repeated prompts to log in which will get me in for a while before the next prompt. However, my Note 5 never stops receiving email... 

    It's absolutely atrocious, that M$ would allow this to continue for as long as it has. You'd think that they would want Mac users to buy their software not run from it. I have attempted every work-around that could be found through a web search and none have stopped it from happening... The only resolution for me was going back to 15.17. I have no issues whatsoever now, but lack all of the updated security and other functional enhancements!

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  4. Anonymous
    2016-07-12T13:48:28+00:00

    same issue here. It's mostly the Outlook prompt, but occasionally the modern auth comes up with the organisation logo. 

    Oddly, the built-in OS X Mail app works without a hiccup, but I shouldn't have to resort to that when using Microsoft software with a Microsoft platform.

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  5. Anonymous
    2016-06-30T15:15:33+00:00

    OSX login password matching Exchange password didn't resolve the issue for me. Within my own wifi everything is fine, but other WiFi (remote) keep on asking for PW. Sometimes it works for 10 minutes, sometimes just a few seconds before it asks again.

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