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
    2016-12-21T22:16:07+00:00

    I was experiencing the exact same problem, the solution is below, no more pain....

    When logging into Exchange or Office 365 using Outlook 2016 for Mac. You receive the error “Authentication failed. Check your account information and try again” or the client simply stops syncing.

    I looked around various forums without any response but found that the cause for me  was due to invalid KeyChain entries. You need to fix the KeyChain on your Mac by trying one of the following:

    Test 1: Reset your iCloud Keychain password

    If you are syncing Keychain Access to iCloud then try resetting the iCloud key by

    1. Opening iCloud under the System Preferences pane
    2. Click Options under Keychain
    3. Click Change Security Code and follow the instructions

    Test 2: Reset default keychain

    If this should not work then you may need to reset your Keychain

    1. Start the app Keychain Access
    2. Open Preferences and select Reset My Default Keychain

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  2. Anonymous
    2016-05-06T13:39:36+00:00

    I stumbled across this thread today as it seems that the bug is back (again). I'm running Mac OSX 10.11.3 with Outlook version 15.21.1.  Just thought I'd throw this back out there in the case that anyone else is running into this again this year and has found a solution.

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  3. Anonymous
    2015-09-11T08:26:34+00:00

    Hello all-

    As the originator of this post - apologies for not updating the content of the main page for a while. In the midst of all these issues, my employer changed the way that remote users connect to corporate Exchange Servers, which now prevents me from using Outlook for Mac at all. Therefore, I haven't had the ability to do my own testing on releases after 15.12.x. That said, it appears that issues related to logon still persist -- which is disappointing. I'll do my best to keep updating that main thread if we find a breakthrough.

    Cheers-

     Seattle_Expat

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  4. Anonymous
    2015-08-17T15:12:44+00:00

    Okay, I had four Exchange entries in KeyChain. Two were private/public keys, and I left those in place. The other two were related to my Exchange account. I deleted both of those.

    I started Outlook, went into Preferences, and deleted my Exchange account. That took a while to run. Once it finished, I quit Outlook and, for good measure, rebooted my system.

    Once back online, I started Outlook, added my Exchange account, and I haven't had a password prompt since. It's only been running for about an hour, but I was getting password prompts every 2-3 seconds before. This is, at a minimum, a huge improvement. I'm keeping my fingers crossed.

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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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