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Strange issue with Outlook in Hybrid Office 365 / Dirsync environment

Posted on 2014-04-09
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Last Modified: 2014-05-14
Hi,

I hope someone can help. We have been running a Hybrid Office 365 environment for almost a year now and are soon going to be moving to a cloud only setup. Around 2 months ago we upgraded Dirsync to Azure Dirsync to allow password synchronisation. This has been working fine but now, we have a strange issue.

If a users AD password expires, they change it. Once they change it, Outlook stops connecting to 365. This is either Outlook 2010 or Outlook 2007. I checked the event viewer and the miis client on the Dirsync server and can see the password sync was successful. Also verified this by logging onto webmail as one of the users in question, with the new password.

To get Outlook to work, I have tried everything I can think of like, clearing credential manager, creating a new Outlook profile etc. and nothing will work. I even tried (in the off-chance) using the old password but this also doesn't work.

What's interesting is, if I log on to a new machine (or one the user hasn't logged onto before) Outlook autodiscovers fine and works without a hitch.

Any idea what could cause that kind of behaviour?

Really need to get this one resolved because as you can imagine, as more and more passwords expire, the problem is going to snowball and I really don't want to set passwords not to expire, even temporarily.

Thanks in advance...
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Question by:ishamsi
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Expert Comment

by:Vasil Michev (MVP)
ID: 39988979
Try re-runing the desktop setup wizard on the affected machine. Also Outlook in safe mode.
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Author Comment

by:ishamsi
ID: 39991163
Hi Vasil,

Thanks but I don't think either of those are the fix. Here's some more info:

Right now, I can’t download the desktop setup wizard. When I click the link on the portal it goes to this url and I get a 404 from the page.

I had a laptop for a user who has the problem a moment ago. She has Office 2010. I patched it to the hilt. Every patch until today. Still the same. Reinstalled MS Office – same. Created new local profile for user – same. The fix was to remove every profile for Outlook (Control Panel > Mail) and rename C:\Users\<username>\AppData\Local\Microsoft\Outlook to Outlook.old. I then opened it Outlook. It autodiscovered, configured the mail account fine and worked.

As I say, Dirsync has been working and people have been changing passwords fine up until this weekend.

The symptoms are that, no matter what I do in Outlook or Mail in Control Panel it either cannot find the user or won’t accept their password.

Does anyone have any other ideas? Really need a fix ASAP.

Thanks again.
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LVL 14

Expert Comment

by:BlueCompute
ID: 40027254
You do know you get free support with Office 365 right?   What do MS have to say about it?  What methods do they use to reconnect the Outlook profile if you give them access to one of the broken machines?
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Accepted Solution

by:
ishamsi earned 0 total points
ID: 40053147
Our Office365 subscription is provided by a 3rd party so the support link goes to them. In any case, I've got it sorted...ish. The fix seems to have been patching. Updated Office 2007 to SP3 and 2010 to SP2. There are still some lingering issues but that seems to have ultimately been the fix. Thanks for all the suggestions.
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Author Closing Comment

by:ishamsi
ID: 40064011
Issue was lack of patching on Office installations.
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