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
    2016-12-27T16:17:23+00:00

    It is now Dec 27th 2016 and we are experiencing this issue, after deleting the Keychain for Exchange it will prompt for normal login which it accepts but after a couple seconds we get the ADFS login prompt like loging in from home to Office 365 on Chrome or FireFox which we have never seen before for any Outlook whether MAC or Windows in native Outlook, usually once we login with the normal login it works fine unless account is locked or expire which still never shows a ADFS login - Very odd!!

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  2. Anonymous
    2016-12-21T22:18:00+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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  3. Anonymous
    2016-12-21T22:17:15+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

    Was this answer helpful?

    0 comments
  4. 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

    Was this answer helpful?

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  5. Anonymous
    2016-12-20T16:09:39+00:00

    This problem is annoying at best.  The curious issue for me is that I have a repeated prompt through the day when at the office.  Strangely, however, I have no issues when connected to the same exchange server through VPN from home.

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