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
    2015-08-21T11:44:29+00:00

    I got rid of passwords prompt using 15.13.1. However i notice that the status in lower right hand corner toggles frequently between "Connected" and "Not connected".

    I also noticed that outgoing mail will be stuck in Outbox and a Sync error is raised "An unknown error has occurred in Outlook. Mail could not be sent."

    Once Outlook for any reason get connected the mail is sent.

    Anyone having the same issue, any solution?

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  2. Anonymous
    2015-08-18T18:53:00+00:00

    Oh come on...lets not reduce this to a rantfest with contribute something of value or reconsider posting at all.

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  3. Anonymous
    2015-08-17T17:35:14+00:00

    I'm up to date on 15.13.1 and password prompts have stopped.  But, it wasn't without some work.  Keychain does still seem to be involved and it has not been fixed (still appending the wrong domain).  But, entering the username without domain of any kind was the only thing that worked for me.  Could not get domain\username to work and username@domain didn't work either.  This does not seem to be consistent for other users, so I would not call this clearly corrected yet.

    So far, no password prompts unless I delete all keychain entries. Then the prompts come back until I enter in proper format (no extra stuff).

    Let's hope this gets cleaner still in 15.13.2

    By the way...:

    Tested on two desktops, one laptop, different locations and different setups including VPN - all running 10.10.5 - same results

    I will reiterate that this was never a problem for one desktop inside organization network, so I still suspect this is roaming or offsite issue.  But, could be wrong on that.

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  4. Anonymous
    2015-08-17T16:57:04+00:00

    After upgrading to 15.13.1 I was getting password prompts more frequently than with any other version. In many cases, Outlook wouldn't reconnect to Exchange even after entering the correct password. 

    I tried these steps: delete keys, delete exchange account, reboot for good measure, restart outlook and add the exchange account. 

    Haven't had a password prompt yet since doing that, and my laptop was unattended (and in sleep mode) for a while. Normally, reviving my laptop after it was inactive & asleep was a password-prompting nightmare. This is an improvement, by far. Thanks for sharing your steps - they helped me out!

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  5. Anonymous
    2015-08-15T02:00:22+00:00

    You have to upgrade to 15.12.3 first and then check for updates again (if it doesn't happen auto-magically when the update finishes). You should see the 15.3.1 update after that.

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