Connecting the world…


Microsoft Outlook through Citrix Access Gateway SSL IP VPN

One of our customers wants you use their locally installed Microsoft Outlook through a Citrix Access Gateway (CAG). Sales people from that customer travel through the country and use the Outlook offline to read or prepare e-mail to send later. These people use UMTS technology to connect their laptops to the Internet. The customers wants these sales people to have the ability to use their Outlook offline and actually send/receive mail when connected to a network with Internet access.

The customer is using CAG’s to publish multiple services to the Internet, so together with my colleague Edwin Houben from DigiPulse, we started to look at a suitable solution. The CAG is located behind a CheckPoint firewall and traffic to the internal network needs to go through an ISA server firewall.

First we started to look at the ports Microsoft Outlook uses to connect to the Exchange server. Looking at the settings from a laptop, the connection is made by FQDN of the Exchange server. While performing a netstat -na we noticed that Outlook uses two ports to connect to the Exchange server.


The Outlook clients connects to the Exchange server on FQDN. So the laptop needs to have an IP connection to the Exchange server. So we decided to use the Citrix Secure Access Client to give the user the ability to establish an secure IP connection to the network.

Looking at the customers network, we had to configure access-lists on two locations to make the solution more secure. The first location is a Network Resource in the CAG. The Network Resource enables only the above ports to the Exchange server IP address. The second location is allowing the IP address of the CAG to connect to the Exchange server on the above port numbers through the ISA server.

After configuring both access-list, we did some testing and the solution works perfectly. You can now use the laptop on the internal network and externally with the Citrix Secure Access Client without making any changes in the Outlook configuration.

Later, the customer noticed that he couldn’t use Microsoft Outlook anymore in conjunction with the Citrix Secure Access Client. After digging a bit deeper in the traffic flow between Microsoft Outlook and the Exchange server, I noticed that, beside TCP/135, random ports above 1024 are used. So I changed the Network Resource  and the ISA servers to allow TCP/135 and the range TCP/1024-2000. I haven’t used the complete range of registered port numbers, so I hope Exchange doesn’t use a port above TCP/2000.


I didn’t some Googleing (or Googling or whatever) on TCP port 135 and I found some “funny” things:

Some well known Root kits also use this port to transmit data back to home base and download more malware. I also suspect may be an entry point for some root kit /malware for un patched systems or systems that did not patch correctly. Source 

Currently inbound scans are likely the Nachi or MSBlast worms. Source

The problem with port TCP 135 is that it is used for multiple services, which are listed below. So blocking port TCP 135 could affect communication between devices or the usage of services.


Client/Server Communication DCOM DHCP Manager
Exchange Administrator Microsoft Message Queue Server RPC User Manager
RPC Service Manager RPC Port Mapper SCM used by DCOM
SQL Session Mapper WINS Manager  

ISA 2006 Authentication over HTTP

I implemented different ISA 2006 Reverse Proxy servers in conjunction with Microsoft Exchange 2003 or Windows Exchange 2007.

Today I configured ISA 2006 with Exchange 2007. I configured the Reverse Proxy server as I did always. And the connection from outside the network works perfectly. On the internal Exchange server I configured Basic and Integrated Authentication on the OWA virtual directory. The problem is that internal users now automatically log in to their webmail box when entering the URL from the Exchange server.

This is not the desired configuration, because internal users should be able to open other people’s mailboxes by logging in as that user. The customer also has an ISA 2006 on the internal network for forwarding proxy purposes.

I decided to publish Exchange 2007 on the internal ISA 2006 server as well. The configuration should use Form Based Authentication (FBA) over HTTP. After configuring and trying the connection, the user can’t access the ISA logon page. In the logging you find that Authentication over HTTP isn’t allowed.

Error Code: 403 Forbidden. ISA Server is configured to block HTTP requests that require authentication. (12250)

This is a default setting in ISA 2006 which can be disable. To allow Authentication over HTTP go to the Listener configuration. Go to the Authentication tab and Select Advanced. In the next tab enable the option Allow client authentication over HTTP. This option enables the using FBA over HTTP.

Exchange 2007 with ISA 2006

Today I have be working on publishing Microsoft Exchange Outlook WebAccess and Active Sync to the Internet. We had some discussions with some Microsoft Consultants about a secure way to publish Outlook Web Access to the Internet, especially the authentication part of such a solution.

Some people are talking about publishing OWA directly to the Internet. In my opinion, this results in a major security thread, because you directly publish a TCP/80 and TCP/443 connection from the Exchange server to the Internet. An vulnerability or exploit in these services could end up in an hacker who takes over the Exchange server.

A second solution is placing a front-end server in a DMZ segment, but making the server a domain member for authentication. In my opinion still a security leak, because somebody who hacks the DMZ server has maybe the ability to hack or corrupt the Active Directory.

The third solution, and the solution we advise, is using a Microsoft ISA 2006 server as a front-end server in the DMZ. We configure a RADIUS or LDAPS (if you would like the option to change the password) connection to a RADIUS server or a domain member on the internal LAN segment. This ensures a secure way of authenticating users and even if somebody hacks the ISA server, he still hasn’t hacked a domain member server or a vulnerability in TCP/80 or TCP/443 of the Exchange server.

I have had a lot of help of an article on from Thomas Shinder while configuring the solution. I had some problems with publishing Active Sync. Ended up with enabling Basic Authentication on the Active Sync virtual directory (Microsoft-Server-ActiveSync).