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Outlook anywhere issue with another site exchange 2010

Posted on 2014-01-29
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Last Modified: 2014-02-10
Hi,

I have the below setup

Site1:

2 AD servers
2 HUB/CAS server (2010)
2 Mailbox Server (2010)

Public name to configure outlook anywhere: mail.company.com Public IP eg: 86.86.86.100
Autodiscover.company.com 86.86.86.100

Site 2:

1 AD server
1 all in one exchange 2010 server

Public name to configure outlook anywhere: webmail.company.com, public IP:  eg 56.56.56.100




1. Users of site 1 having no issue in accessing mails via outlook anywhere
2. Users of site 2 having issue in accessing mails via outlook anywhere. password prompting continuously.

What might be the issue? How to resolve this.
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Question by:kolathaya123
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5 Comments
 
LVL 63

Assisted Solution

by:Simon Butler (Sembee)
Simon Butler (Sembee) earned 500 total points
ID: 39817691
Trusted certificate installed on both locations?
Has it ever worked?
Does Autodiscover work for the users in the second site?

Run a test account through the Microsoft test site http://exrca.com/

Simon.
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LVL 12

Expert Comment

by:Md. Mojahid
ID: 39820240
First check your ssl certificate and also check external DNS resolved properly.
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Author Comment

by:kolathaya123
ID: 39820423
yes.. SSL certificate has all the exchange servers in both site.

in the second site the webmail.company.com is resolving to one IP (site 2 exchange server) and autodiscover.company.com is resolving to site 1 exchnage. Will this setup work?
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LVL 12

Expert Comment

by:Md. Mojahid
ID: 39820449
did your check user authentication setting on exchange server.
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LVL 63

Accepted Solution

by:
Simon Butler (Sembee) earned 500 total points
ID: 39821515
Autodiscover going cross site is fine. However Autodiscover.example.com is not used internally unless you have configured Exchange to do so.

get-clientaccessserver | select identity, autodiscoverserviceinternaluri

Autodiscover is AD site aware, so you can have different values for that on different AD sites.

Run a test account through the Microsoft test site at http://exrca.com/ 

Simon.
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