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ISA Server 2006 array – renew certificate

When configuring a Microsoft ISA Server 2006 array you have two options for authentication and communication between the Microsoft ISA 2006 Configuration Storage Server and the array members.

  • Windows Authentication: Choose this option if ISA server and the Configuration Storage server are in the same domain, or in different domains with a trust relationship between them. The connection will be encrypted (signed and sealed);
  • Authentication over SSL encrypted channel: Choose this option if ISA server is in a domain that does not have a trust relationship with the Configuration Storage server domain, or if it is part of a workgroup. The connection will be SSL encrypted.

I normally configure the array members within a DMZ environment en install the CSS server on the internal network.

To maximize the security the array members aren’t part of the Active Directory. So communication between the CSS and the array members is workgroup based and the authentication type used is Authentication over SSL encrypted channel. This option needs the configuration of SSL certificates to authenticate and secure the connection. The certificates have a certain validity period, after which the certificate needs to be renewed.

Normally I always ran the repair option from the installation and specified the new certificate. I discovered a new and simpler method by using the ISACertTool. This tool provides an easy way to renew the certificate on the Configuration Storage Server and the root CA certificate on the array members.

You just need to create a web server certificate in pfx format from a Windows CA server of any other CA server. If the CA server isn’t trusted by the array members, you need to install the CA certificate on the array members. If you use trusted CA server certificate, you can skip this step.

The syntax for the ISACertTool is very straightforward. On the Configuration Storage Server you need to run the following command:

ISACertTool.exe /st <pfx file> /pswd <password> /keepcerts

On the array member you run the following command to install the root CA certificate.

ISACertTool.exe /fw <root ca file>

IMPORTANT: for a correct usage of the tool you need to extract the tool to the Microsoft ISA Server install directory, which is by default C:\Program Files\Microsoft ISA Server.

VMware: upgrade VMware Tools and Virtual Hardware for Microsoft ISA array

Today I have been troubleshooting problems with a Microsoft ISA array. The array didn’t function anymore after moving the Configuration Storage Server and one array member from a VMware 3.5 environment to a VMware 4.0 environment. After moving the array member the VMware Tools were upgraded and also the Virtual Hardware was upgraded. After rebooting the moved array member the customer received multiple error messages, like duplicate IP addresses and users not able to access resource through the reverse proxy.

A Microsoft ISA array uses Network Load-Balancing and NLB was the cause of all problems. After upgrading the VMware Tools and the Virtual Hardware, NLB needs to be reconfigured. The complete configuration of NLB was lost. I reconfigured NLB (multicast with IGMP support) and the problem was resolved. The array members were functioning properly again.

Moving and upgrading the second array member resulted in the same problems with the same cause. Reconfiguring NLB on the second array member did the trick. So be careful when moving ISA array members with NLB configured from a VMware 3.5 to a VMware 4.0 environment, especially when upgrading VMware Tools and the Virtual Hardware.