Avatar of Paul-Anthony
Paul-Anthony
Flag for Australia asked on

Exchange 2010 - Outlook keeps popping up asking for credentials

Environment:
Server side:

Windows SBS 2011
Exchange 2010
Client Side:
Outlook 2010
Windows XP / 7 Pro


Problem:
Outlook users continually have user credentials pop up appear

I have tried doing some research
Some of the solutions was to disable Outlook Anywhere in Outlook
un-ticking "connect to Microsoft Exchange using HTTP"
When you restart outlook, Outlook Anywhere is re-enabled

I am wondering what do i have to change server side to fix this issue,

Thanks in advance
ExchangeOutlook

Avatar of undefined
Last Comment
Simon Butler (Sembee)

8/22/2022 - Mon
R--R

First run outlook.exe /rpcdiag and check if outlook is connecting using http.
In outlook check the test-email autoconfiguration if there is any error.
Is the outlook is in the local network then uncheck "On Fast networks, Connect using HTTP first, then connect using TCP/IP”
Paul-Anthony

ASKER
Thanks R-R for your feedback
To me it looks like that it's connecting via TCPIP  (see attached)
The setting is already unchecked "On Fast networks, Connect using HTTP first, then connect using TCP/IP”

....
screenshot.fw.png
dsnegi_25dec

it looks totally a certificate issue.

Is issue with both windows ?
Experts Exchange has (a) saved my job multiple times, (b) saved me hours, days, and even weeks of work, and often (c) makes me look like a superhero! This place is MAGIC!
Walt Forbes
Simon Butler (Sembee)

The Outlook Anywhere setting is NOT the cause of this.
People go after that for some reason, find that it seems to work, when it hasn't really, because Autodiscover just puts the setting back. Just because the client is configured to use Outlook Anywhere doesn't mean it will.

The primary reason for this problem is, as already mentioned - SSL certificates.
Exchange 2010 (which is in SBS 2011) uses SSL certificates for all client communications, not just Outlook Anywhere. If there is a problem with the SSL certificate then Outlook will often throw an authentication prompt - mainly because it doesn't know what else to do.

Therefore the first question has to be - do you have a trusted SSL certificate on the server?
If so, was it installed through IIS, SBS or Exchange?

Simon.
Md. Mojahid

Check your ssl certificate and discuss with your ssl certificate provider.
Paul-Anthony

ASKER
Thanks everyone for your reply!
The SSL Certificate was purchased through DigiCert Unified Communications Certificate
and was installed through  Exchange
Would you suggest removing and reinstalling the certificate?
⚡ FREE TRIAL OFFER
Try out a week of full access for free.
Find out why thousands trust the EE community with their toughest problems.
ASKER CERTIFIED SOLUTION
Simon Butler (Sembee)

THIS SOLUTION ONLY AVAILABLE TO MEMBERS.
View this solution by signing up for a free trial.
Members can start a 7-Day free trial and enjoy unlimited access to the platform.
See Pricing Options
Start Free Trial
GET A PERSONALIZED SOLUTION
Ask your own question & get feedback from real experts
Find out why thousands trust the EE community with their toughest problems.