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Outlook is asking for password

Posted on 2014-08-20
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Outlook is keep prompting for a password.
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Question by:Stelian Stan
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by:Adam Farage
ID: 40275199
What version of Exchange?  If you close Outlook and run the following what is the connection type into Exchange?

outlook.exe /rpcdiag

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Cheers!
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Expert Comment

by:David Paris Vicente
ID: 40275202
Try changing the profile first.

open control panel/mail/select the profile and click properties

select the mailbox and click the change button.

when inside the profile you will see tabs at top for connection and security.

Please make sure you have selected negotiate authentication, and have unchecked

the box that states Always prompt for login credentials....

then check if you are using http to connect with exchange, if so uncheck this and apply the changes. Close outlook if open and re-open outlook.

If this doesn't help you have check the authentication settings in your exchange server, OWA, Outlook Anywhere.

Let me know if this helps...
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Author Comment

by:Stelian Stan
ID: 40275209
Thank you guys for quick response.
David
Is not the profile because this happens even on a new computer / user / Outlook profile.
Adam
I will try that tomorrow morning and let you know.
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Expert Comment

by:Adam Farage
ID: 40275293
Stelian,

If its Exchange 2007-2013, I probably know the answer.. but before I write a paragraph on it I would rather like to confirm the connectivity method that Outlook is using (screen shot the /rpcdiag for me once Outlook is fully opened), the version of Outlook along with the exact version of Exchange.

Thanks bud!

**edit**

Spoiler alert: it is most likely the Outlook profile will show in the /rpcdiag that they are connecting over HTTP (or HTTPS), which is Outlook Anywhere. In Exchange 2007 / 2010 (they finally fixed this mess in 2013) Outlook Anywhere (RPC / HTTPS) default's authentication is basic. If you change the IISAuthenticationMechanism to NTLM for Outlook Anywhere, Autodiscover will update the clients and utilize the existing kerberos tokens on the client machines (e.g: basic cannot utilize the existing kerberos token on the machine from a domain joined client, thus the reason you are being prompted for a password).

I will give you more directions if we can reproduce the issue, and confirm that this is the cause.
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Author Comment

by:Stelian Stan
ID: 40276457
outlook
Hi Adam,

Attached you have a screenshot of "outlook.exe /rpcdiag".
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Expert Comment

by:Adam Farage
ID: 40276567
Did it ask for the password initially?
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Expert Comment

by:Mohammed Yusuf Panjri
ID: 40276571
Check if the outlook prompts in Online Mode and Cached Mode, if the Outlook is prompting only in cached mode then it could be OAB issue, if Outlook is prompting for password in both mode than check the IIS authentication set as per article  http://technet.microsoft.com/en-us/library/gg263433(v=exchg.80).aspx
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Expert Comment

by:Adam Farage
ID: 40276580
What version of Exchange is this? 2007?
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by:Mohammed Yusuf Panjri
ID: 40276587
Hi Adam,

if you check the Screen Shot Shared...The version is showing there.... :)
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Expert Comment

by:Adam Farage
ID: 40276609
Ah, there it is!

So back to the OP, I would check to make sure the permissions within IIS are set properly. Go ahead and check that out, as you are using MAPI.NET (RPC/TCP = TCP/MAPI for this test) and not RPC/HTTPS (it would have shown as HTTPS). If a virtual directory has the incorrect permissions, this would cause this error in a heartbeat, since it would need to authenticate to obtain access to it :)
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Author Comment

by:Stelian Stan
ID: 40278979
Sorry guys for late response, so:

Did it ask for the password initially?
- YES it ask for password right after I create a new profile.

Mohammed - it only prompts for password on cached mode. I will check that article later today.

Adam - i will check IIS permissions according to the article provided by Mohammed and will let you guys know the result.
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Accepted Solution

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Stelian Stan earned 0 total points
ID: 40340157
Found the issue eventually. It was a certificate mismatch.  Replaced the certificate and now life is good.

Thank you guys for all your help.
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Author Closing Comment

by:Stelian Stan
ID: 40348370
Found the solution myself .
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