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Outlook 2003 and Exchange 2010

Posted on 2011-09-05
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Last Modified: 2012-08-14
I have a small business client and they have some remote working staff. How do i setup outlook 2003 to access the exchange server remotely. They have access via the remote portal at the moment but dont want this. they want outlook to connect directly to the server.
Some of these workers use XP home.
Thanks in advance
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Question by:TrenchControl
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LVL 4

Expert Comment

by:Daelt
ID: 36483537
setup a VPN and that should work like it's being on local network
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Expert Comment

by:josrex
ID: 36483569
To configure Outlook 2003 to work with Exchange Server 2010 without need of an VPN, you can have a look on the article on below link.

http://exchangeserverpro.com/how-to-configure-exchange-server-2010-outlook-anywhere

Be ensure that you followed MS KB article while configuring Outlook to work with Exchange Server 2010

http://support.microsoft.com/kb/2006508/en-us
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Expert Comment

by:5g6tdcv4
ID: 36483890
The one thing that is not mentioned in article is the need for a server certificate.
http://blogs.catapultsystems.com/IT/archive/2010/02/17/exchange-2010-part-2-of-4-%E2%80%93-understanding-the-new-uc-san-certificate-requirement.aspx

Also if you run into  any problems with external clients accessing outlook anywhere or using mobile phones externally connected to exchange use www.testexchangeconnectivity.com to to troubleshoot problems
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LVL 4

Expert Comment

by:HostOne
ID: 36487478
Hi,

To enable Outlook 2003 to work with Outlook Anywhere (RPC over HTTPS in Exchange 2010), you only need to enable Outlook Anywhere on the Exchange server. If you don't know how to do that, please let me know.

Then on the Outlook 2003 client you need to do the following:
1. Start up a new exchange account.
2. When you set up the account, insert the server name (fully qualified) and the user name and then hit more settings *before* you test the user name.
3. Go to security and tick the box "encrypt data between office and exchange" (the actual text of that option is longer but you'll see it).
4. Go to connection tab and pick connect to exchange mailbox using http. Tick the proxy settings option.
5. the https:// server option at the top is your exchange server's public server name. No / or /owa or /exchange - just the server name.
6. tick on fast and on slow networks.
7. Tick the appropriate authentication for your server. Probably basic.

Assuming you don't have a real certificate but are instead using a self signed one:
Now, go to Internet Explorer (not firefox, or chrome). Go to https://your.server.
When the cert comes up in red, install it but don't just click next. Make sure you select the location and install it into the Trusted Root Certificates. It will ask if you're sure - you are. ;-)

Now go finish the Outlook set up.

I have dozens of machines running Outlook 2003 connected to Exchange 2010 in this fashion, so you should be fine.
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LVL 5

Expert Comment

by:lloydsystems
ID: 36487884
With regards to your question please see a quick guide on how to set-up Outlook anywhere without using a VPN client. The steps are very easy to follow.
http://office.microsoft.com/en-us/outlook-help/use-outlook-anywhere-to-connect-to-your-exchange-server-without-vpn-HP010102444.aspx

Hope this helps :)
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Author Comment

by:TrenchControl
ID: 36488085
Hi

I have made all the change as mentioned in the solution above but i keep getting the message
"The connections the the Exchange server is unavaible Outlook must be online or available to complete this action"

Any ideas ?

Thanks
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LVL 13

Expert Comment

by:5g6tdcv4
ID: 36488127
Www.testexchangeconnectivity.com
Do the outlook anywhere test. If it fails it will tell you where the problem is with your setup
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Expert Comment

by:HostOne
ID: 36488276
TrenchControl, if you're using Outlook 2003 you must manually tick the encrypt data between outlook and exchange option. This is required by Exchange 2010 and off by default on 2003. See my comment above.

If you don't do this, you will get the error you describe.
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Author Comment

by:TrenchControl
ID: 36489400
I have checked the encrypt data box, and outlook anywhere is enabled - i will run a test now
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Author Comment

by:TrenchControl
ID: 36537318
Testing RPC/HTTP connectivity.
 The RPC/HTTP test failed.
 
Test Steps
 

Attempting to resolve the host name remote.contessa.ie in DNS.
 
The host name resolved successfully.
 
Additional Details
 
IP addresses returned: x.x.x.120
 
Testing TCP port 443 on host remote.contessa.ie to ensure it's listening and open.
 
The port was opened successfully.
 
Testing the SSL certificate to make sure it's valid.
 
The SSL certificate failed one or more certificate validation checks.
 
Test Steps
 
ExRCA is attempting to obtain the SSL certificate from remote server remote.contessa.ie on port 443.
 
ExRCA successfully obtained the remote SSL certificate.
 
Additional Details
 
Remote Certificate Subject: CN=remote.contessa.ie, Issuer: CN=contessa-SERVERCENTRAL-CA.
 
Validating the certificate name.
 
The certificate name was validated successfully.
 Additional Details
 
Host name remote.contessa.ie was found in the Certificate Subject Common name.
 
Certificate trust is being validated.
 
Certificate trust validation failed.
 
Test Steps
 
ExRCA is attempting to build certificate chains for certificate CN=remote.contessa.ie.
 
A certificate chain couldn't be constructed for the certificate.
 Additional Details
 
The certificate chain couldn't be built. You may be missing required intermediate certificates.
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LVL 13

Expert Comment

by:5g6tdcv4
ID: 36537391
Is this a self-signed certificate?
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Author Comment

by:TrenchControl
ID: 36537544
Yes it is.
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LVL 13

Expert Comment

by:5g6tdcv4
ID: 36537564
so you need an actual certificate unless you want to install the certificate on all of the clients, including the intermediate certs,
here is a guide to creating and installing the 2010 cert from a certificate provider
http://blogs.catapultsystems.com/IT/archive/2010/02/17/exchange-2010-part-2-of-4-%E2%80%93-understanding-the-new-uc-san-certificate-requirement.aspx
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Author Comment

by:TrenchControl
ID: 36537605
Am i worng in assuming that the self signed cert will not work on outlook 2003 with 2010 ? I have only 3 clients that are remote workers and they are not added to the network. Outlook 2010 is working fine at the moment remotely on a machine that is on the network ?
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LVL 13

Expert Comment

by:5g6tdcv4
ID: 36537633
so you are saying the remote client (2010) who are domain joined are working, and outlook 2003 client who are not domain joined are not working?
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Author Comment

by:TrenchControl
ID: 36537664
That is correct. I made all the changes to the outlook 2003 etc after downloading the cert from the portal and installing it. Should it not work for any of the clients ?
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Accepted Solution

by:
5g6tdcv4 earned 500 total points
ID: 36537784
what version of Service pack is running on exchange/SBS?
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Author Comment

by:TrenchControl
ID: 36541658
version 14.01.0218.013
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Author Closing Comment

by:TrenchControl
ID: 36574400
Ta
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