User can't sync to Exchange Online

Tarkisal
Tarkisal used Ask the Experts™
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I have a user that recently changed their password for Office 365/Exchange Online. After doing so it won't let her sync her Outlook 2010 and keeps asking for a password. The password she is using is correct and we tested it by going through the Outlook portal online. Also, I was able to setup Outlook 2010 on a different computer using her credentials without issue. Further, I was able to setup Outlook on her computer using my credentials. So the problem doesn't appear to be Office 365 based as she can sign in online and she can sync with Outlook on a different computer. But the fact that I can setup Outlook 2010 on her computer using a different problem tells me it's not a computer issue either - unless there is something stuck somewhere on her computer that won't let her use the new password.

I have tried clearing out the whole mail profile (Start - Control Panel - Mail (32 bit) and try recreating the profile several times with no luck. Each time it finds her profile but then prompts her to put in the password she just put in. It won't get passed that "Windows Security" box that pops up looking for the new password.

I also tried clearing out any files within the c:\users\-username-\appdata\local\microsoft\Outlook folder but the problem remains.

Any help would be appreciated.
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Jon BrelieSystem Architect

Commented:
Assuming this is the only outlook profile you need on the client pc, delete everything under:
HKCU\Software\Microsoft\Windows NT\Current Version\Windows Messaging Subsystem\Profiles

http://netport.org/?p=1421

Author

Commented:
Thanks for the response!

I followed that path but found there were no sub-folders under the Profiles folder. I assumed it was because there was no mail profile set and, sure enough, when I went through the process of putting in the mail profile the new sub-folder with the name of that profile showed up. However, I can't finish the process because it starts prompting the user for a password again. The only other thing I see under profile is a REG_SZ file labeled (Default) and data with (value not set.) But it won't let me delete this anyway.
Jon BrelieSystem Architect

Commented:
Strange behavior.  Does the old password work?
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Author

Commented:
No, I tried that as well but no luck. I'm sure it's a something on the computer because the new password works on another machine and through the online portal. I'm hoping letting it sit overnight will help it sync...
Top Expert 2016

Commented:
check the credential manager in control panel.

Author

Commented:
David,

I really thought you had something there. I checked the credential manager and there were three entries for Outlook for that user. However, clearing them out still results in the same problem.

It's definitely something with her profile, though. When I sign in as myself on her computer but then try to connect to her e-mail address it works. I could just blow away her profile but that would be a last resort. I'm hoping I can zero in on the actual reason this is happening and fix it without going with the "nuclear option."
System Architect
Commented:
When I'm troubleshooting things like this, I usually dismantle the profile, rather than delete it entirely.

Start exporting and deleting keys from her reg hive.  I would start with HKEY_CURRENT_USER\Software\Microsoft\Office\Outlook

If that doesn't do it, export and remove
HKEY_CURRENT_USER\Software\Microsoft\Office\14.0\Outlook and try again.

then: HKEY_CURRENT_USER\Software\Microsoft\Office

Keep stripping away pieces until the issue goes away.  Then you can review the content of the exported files and compare them against functional users to see if you can isolate the issue.

If peeling the registry doesn't work, start in on profile folders and keep working your way up the tree.

Author

Commented:
I was able to get it to work. I took your advise and pulled out each registry file as I went but I couldn't seem to narrow down where it came from. Unfortunately, due to time constraints, I had to give up digging deeper and rebuilt the user's profile. This cleared up the problem. I'm still convinced it was something in the registry, though, so I'm giving you the credit for the solution. Thanks for your help!

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