Janalent KB ISA LDAPS Configuration Guide

ISA Server 2006 Configuration Guide for:
Publishing SharePoint/OWA via Standalone ISA Server
Document Abstract:
This document provides a step-by-step guide to properly configure publish SharePoint through ISA using
LDAPS for authentication.
Author(s):
Elias Hill
Janalent
knowledge . wisdom . performance
Copyright Janalent North America LLC, All rights reserved
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Item Details
Document Title ISA Server 2006 Configuration Guide for: - Publishing SharePoint/OWA via Standalone ISA Server
Creation Date 12/13/08
Last Updated 07/09/09
Authors Elias Hill
Date 12/13/08
Version number 0.0.1
Janalent– Knowledge, Wisdom, Performance

Janalent North America, LLC
2 7251 W Lake Mead Blvd, Suite 300 | Las Vegas, NV 89128
Phone: +1.888.290.4870 | web: www.janalent.com | email: info@janalent.com
Copyright 2008 – Janalent North America LLC. All rights reserved
Table of Contents
Document Control & Sign-off ........................................................................................................................................2

About the Authors .....................................................................................................................................................4
Overview ........................................................................................................................................................................5
Document Scope .......................................................................................................................................................5
Assumptions ..............................................................................................................................................................5
High Level Processes .................................................................................................................................................6
Procedures .....................................................................................................................................................................7
Install an Enterprise Root CA in the Authenticating Domain ....................................................................................7
Configure ISA for LDAPS Authentication .................................................................................................................14
Publish the SharePoint Sites in ISA ..........................................................................................................................18
Test Connectivity to LDAPS Server (fail) ..................................................................................................................23
Enable Certificate Auto-Enrollment in the Domain .................................................................................................25
Export CA Root Certificate and Install on the ISA server .........................................................................................27
Test Connectivity to LDAPS Server (success) ...........................................................................................................37
Validate Site Access, SSO and File Upload Functionality .........................................................................................39
Janalent – Knowledge, Wisdom, Performance

Janalent North America LLC
About the Authors
Elias Hill, Manager of Solutions Architecture, Janalent North America
Eli is an Enterprise Solutions Architect and is a multi-disciplined expert in messaging & collaboration system
solutions and network engineering. He has over 10 years experience in designing, deploying, and maintaining
directory, messaging, and network systems in large, complex, global enterprises.

ISA S ERVER 2006 C ONFIGURATION G UIDE FOR :
Overview
In many deployments of SharePoint or OWA, it is common to publish sites using an ISA server that might be a
member of a domain. As a member of the domain, an ISA server can authenticate users without much
configuration. However, in most enterprise environments, it is atypical to have the perimeter network
infrastructure leveraging an ISA server; more frequently, appliance firewalls (Cisco, Juniper, Checkpoint, etc) are
deployed. In these scenarios, the ISA server would likely be deployed as a reverse proxy for published client access
for Microsoft applications, including Exchange, SharePoint, and Office Communication Server. In this context, the
reverse proxy is often located in a DMZ, where traffic is tightly managed. Here, not only would it likely violate the
security policy, but is also unsupported and impractical to open up all the necessary ports to support a domain
member across a firewall. A more desirable solution would have the ISA server authenticating users via LDAPS
(secure LDAP, tcp/636), which is characterized by two operational parameters:
1. The client and server establish TLS before any LDAP messages are transferred
2. Once TLS closes, the LDAPS connection must be closed
Furthermore, by leveraging HTTPS to client access applications and LDAPS to a designated domain controller, users
can change passwords and be informed of password expiration. In this way, one can approach enterprise clients
with a solution that not only achieves advertised features of Microsoft client access applications, but also satisfies
security policies (i.e. two (2) standards-based, encrypted ports: tcp/443 and tcp/636). Note: Although outside the
scope of this document, two-factor authentication mechanisms are also supported in this context.
Document Scope
This document provides a step-by-step guide to demonstrate and explain how to publish SharePoint sites, using
LDAPS as the authentication mechanism for domain users. There are a few sections that deviate from a “perfect”
installation to provide the reader with troubleshooting procedures. This content of this document is generic and
may not fit every scenario.
Assumptions
 Domain controllers are running Windows Server 2008.
 A wildcard certificate has been procured (e.g. *.genericcompany.com).

 The public-facing DNS zone file has been updated with host entries for all published sites.
 SharePoint is running on MOSS 2007; in this scenario, there are five (5) sites with distinct host headers
ending with the same domain suffix. Each site has been properly configured for SSL, including AAM
(Alternate Access Mapping). Note: SharePoint configuration is outside the scope of this document.
 The firewall, running ISA Server 2006, is not a member of the eApps domain; instead, it is member of the
Janalent production domain.
 All client-server/server-server interactions must be encrypted.
 SSO (single sign-on) and FBA (forms-based authentication) must be enabled. Note: SharePoint
configuration is outside the scope of this document.
 Users must be able to change passwords through the published web interface.

High Level Processes
The following procedures will be described:
1. Install an Enterprise Root CA in the Authenticating Domain

2. Configure ISA for LDAPS Authentication
3. Publish the SharePoint Sites in ISA
4. Test Connectivity to LDAPS Server (fail)
5. Enable Certificate Auto-Enrollment in the Domain (optional); just be sure that the CA has issued to the
domain controller used for LDAPS inquiries by the ISA server
6. Export CA Root certificate and Install on the ISA server
7. Test Connectivity to LDAPS Server (success)
8. Validate Site Access, SSO and File Upload Functionality
Internet
Client
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AP 36)
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Figure 1 Considered network topology for ISA using LDAPS for authentication
Procedures
Install an Enterprise Root CA in the Authenticating Domain
On the designated domain controller (used for LDAPS), launch computer management and add a new role. Check
Active Directory Certificate Services.

Click Next
Select Certification Authority and click Next

Select Enterprise and click Next
Select Root CA and click Next


Select Create a new private key and click Next
Accept the default cryptographic settings (RSA#Microsoft Software Key Storage Provide, sha1, 2048) and click Next

The default common name is acceptable, but note that the name cannot be altered in the future without
rebuilding the entire certificate chain. Click Next.
Set the validity period to an acceptable value (in this case, 10 years) and click Next

Select the locations for the certificate database and log files (here, defaults) and click Next
Review the configuration, noting the warning about changing the name of the server, and click Install

Note the successful installation and click Close

Configure ISA for LDAPS Authentication
On the ISA server, populate the HOSTS file referencing the LDAPS provider by its FQDN; later on, the certificate
auto-enrollment process on enterprise CA will issue a certificate to the domain controller (in this case, to itself)
using the FQDN so using any other name in the LDAPS authentication will result in an error.
In the ISA 2006 console, navigate to Configuration  General and select Specify RADIUS and LDAP Servers

Select the LDAP Servers tab and click Add…
Provide the FQDN of the domain controller that will server that will respond to LDAPS. Server description is
optional. The default timeout is 5 seconds. Click OK.

Provide the correct domain name for the authenticating domain, check Connect LDAP servers over secure
connection, provide a credential to access the directory (domain user is sufficient), and click OK
Provide login expressions to direct authentication query to the correct provider and click OK
In this case, EAPPS\* (NetBIOS) and *@eapps.local (UPN)

Click Apply, wait for the changes to commit and click OK

Publish the SharePoint Sites in ISA
Launch the ISA 2006 console and create a new Web Listener, provide a descriptive name, and click the Listener tab
Create a new listener with a descriptive name.

On the Authentication tab, select HTML Form Authentication, select LDAP (Active Directory), click Advanced…
Check Require all users to authenticate and click OK


On the Forms tab, check Allow users to change their passwords
On the SSO tab, check Enable Singe Sign On, click Add... and provide the appropriate URL suffix. Note the extra
pre-pended period.
.genericdomain.com
Click OK

On the Authentication Delegation tab, select NTLM authentication
Click OK

Click Apply, wait for the changes to commit and click OK

Test Connectivity to LDAPS Server (fail)
To use LDAPS, a server certificate must be installed on the LDAP server and the root certificate from the issuing CA
needs to be installed on the ISA Server computer. This section demonstrates what happens in the absence of the
proper certificates.
LDAPS functionality can be validated using LDP.
Select Connection  Connect…


Provide the FQDN of the designated domain controller, specify the LDAPS port (636), and check SSL.
Note that the LDAPS connection fails with a vague error.

Enable Certificate Auto-Enrollment in the Domain
To satisfy the appropriate requirements for LDAPS, a server certificate must be issued to the domain controller.
Later, the issuing CA root certificate will be installed on the ISA server as a trusted root authority.
In the domain, configure a GPO that automatically enrolls each domain controller with a certificate. Launch Group
Policy Management Editor and edit the Default Domain Controllers Policy. Navigate to Computer Configuration 
Policies  Windows Settings  Security Settings  Public Key Policies  Certificate Services Client – Auto-
Enrollment

Select Enable from the Configuration Model drop-down and check “Renew expired certificates, update pending
certificates, and remove revoked certificates”. Click OK.
Immediately apply the GPO to the domain controller by running gpupdate from the command line.

Export CA Root Certificate and Install on the ISA server
On the enterprise root certificate authority, run MMC.
Select, Add/Remove Snap-in…
Select Certificates and click Add >


Select Computer account and click Next
Select Local computer: (the computer this console is running on) and click Finish

Navigate to PersonalCertificates and be sure to select the root certificate, indicated by the Certificate Template
(Root Certification Authority). Right-click All Tasks  Export…
Click Next

Select No, do not export the private key. Exporting the private key would unnecessarily compromise the security
of the certificate.
Leave the default encoding and click Next

Provide a filename and click Save
Click Next

Note the settings and click Finish
Click OK
Copy the exported certificate file to the ISA server. Launch MMC, add the Certificates snap-in for the local
computer, and, under Trusted Root Certification Authorities, right-click  All Tasks  Import…


Click Next
Browse and locate the certificate file and click Next

Select Place all certificates in the following store, ensure that Trusted Root Certification Authorities is displayed,
and click Next
Note the settings and click Next

Click OK

Note that the root certificate is now listed under Trusted Root Certification Authorities

Test Connectivity to LDAPS Server (success)
LDAPS functionality can be validated using LDP.
Select Connection  Connect…
Provide the FQDN of the designated domain controller, specify the LDAPS port (636), and check SSL.

Note that the output indicates a successful connection; all error codes are zero.

Validate Site Access, SSO and File Upload Functionality
Launch IE on an external computer, browse to a published website and provide an appropriate credential. Note the
FBA interface.

Browse to Share Documents

Upload individual and multiple documents.

To test SSO functionality, manually type another site within the same domain suffix and MOSS instance (i.e.
https://extranet.genericdomain.com/default.aspx)


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ISA Server 2006 Configuration Guide for:

Publishing SharePoint/OWA via Standalone ISA Server

Janalent– Knowledge, Wisdom, Performance

Document Control & Sign-off ........................................................................................................................................2

Janalent – Knowledge, Wisdom, Performance

Elias Hill, Manager of Solutions Architecture, Janalent North America

Janalent– Knowledge, Wisdom, Performance

 A wildcard certificate has been procured (e.g. *.genericcompany.com).

Janalent – Knowledge, Wisdom, Performance

1. Install an Enterprise Root CA in the Authenticating Domain

Domain Controller MOSS or SharePoint

Janalent– Knowledge, Wisdom, Performance

Janalent – Knowledge, Wisdom, Performance

Select Certification Authority and click Next

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Select Root CA and click Next

Janalent – Knowledge, Wisdom, Performance

Janalent– Knowledge, Wisdom, Performance

Janalent – Knowledge, Wisdom, Performance

Janalent– Knowledge, Wisdom, Performance

Janalent – Knowledge, Wisdom, Performance

Janalent– Knowledge, Wisdom, Performance

Janalent – Knowledge, Wisdom, Performance

In this case, EAPPS\* (NetBIOS) and *@eapps.local (UPN)

Janalent– Knowledge, Wisdom, Performance

Janalent – Knowledge, Wisdom, Performance

Create a new listener with a descriptive name.

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Check Require all users to authenticate and click OK

Janalent – Knowledge, Wisdom, Performance

Janalent– Knowledge, Wisdom, Performance

Janalent – Knowledge, Wisdom, Performance

Janalent– Knowledge, Wisdom, Performance

LDAPS functionality can be validated using LDP.

Select Connection  Connect…

Janalent – Knowledge, Wisdom, Performance

Note that the LDAPS connection fails with a vague error.

Janalent– Knowledge, Wisdom, Performance

Janalent – Knowledge, Wisdom, Performance

Janalent– Knowledge, Wisdom, Performance

Select, Add/Remove Snap-in…

Select Certificates and click Add >

Janalent – Knowledge, Wisdom, Performance

Janalent– Knowledge, Wisdom, Performance

Janalent – Knowledge, Wisdom, Performance

Leave the default encoding and click Next

Janalent– Knowledge, Wisdom, Performance

Janalent – Knowledge, Wisdom, Performance

Janalent– Knowledge, Wisdom, Performance

Janalent – Knowledge, Wisdom, Performance

Browse and locate the certificate file and click Next

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Note the settings and click Next

Janalent – Knowledge, Wisdom, Performance

Janalent– Knowledge, Wisdom, Performance

Select Connection  Connect…

Janalent – Knowledge, Wisdom, Performance

Janalent– Knowledge, Wisdom, Performance

Janalent – Knowledge, Wisdom, Performance

Janalent– Knowledge, Wisdom, Performance

Janalent – Knowledge, Wisdom, Performance

Janalent– Knowledge, Wisdom, Performance

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