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MCSE 70-227 Study Guide

Installing, Configuring, and Administering Microsoft® Internet Security and Acceleration (ISA) Server 2000, Enterprise Edition

This exam tests your ability to implement, administer, and troubleshoot information systems that incorporate the Enterprise Edition of Microsoft Internet Security and Acceleration Server 2000. The focus is on the Enterprise Edition, although in a standalone setup there is really no difference between the Enterprise edition and the Standard edition.

The characteristics of the expected scenario, according to Microsoft, are:

n          Between 200 and 26,000+ supported users

n          Multiple physical locations

n          Outbound access for typical client services and applications, such as Web access, e-mail, Telnet, FTP, virtual private networking (VPN), desktop management, and access control policies

n          Hosting of network services, such as internal and external Web hosting, messaging, and firewall

n          Connectivity needs that include connecting individual offices and users at remote locations to the corporate network and connecting corporate networks to the Internet

When you pass this exam, you can achieve Microsoft Certified Professional status. You also earn credit toward the following certifications:

n          Elective credit toward Microsoft Certified Systems Administrator on Microsoft Windows 2000 certification

n          Elective credit toward Microsoft Certified Systems Engineer on Microsoft Windows 2000 certification

Deployment Planning Considerations:

Before your Microsoft Internet Security and Acceleration (ISA) Server deployment, the factors below should be planned for:

n          Network size - how many ISA Server computers to deploy?

n          Array considerations - how to map your ISA servers into arrays?

n          ISA Server mode - firewall, cache, or integrated?

n          ISA Server installation options - whole package or specific options?

n          User needs - what applications and services do your users require?

n          Internet connectivity requirements - how you will physically connect your internal network to the Internet?

System Requirements and Capacity Planning

The minimum non-sense requirements to use ISA Server are:

n          300 MHz or higher Pentium II-compatible processor

n          256 MB of RAM

n          20 MB free hard-disk space

n          One network adapter (as a firewall, you better have at least 2)

The OS requirement:

n          Windows 2000 Server with Service Pack 1 or later, OR

n          Windows 2000 Advanced Server with Service Pack 1 or later, OR

n          Windows 2000 Datacenter Server

Other requirement:

n          For array and advanced policies, you need to have Windows 2000 Active Directory running on your network.

n          To remotely manage ISA Server, you only need to install ISA Management client.

The Microsoft suggested hardware capacity for providing caching:

User base



Disk space for caching

Up to 500 Pentium II, 300 MHz 256 MB 2-4 GB
500 - 1,000 Pentium III, 550 MHz 256 MB 10 GB
More than 1,000 Two ISA Server computers with Pentium III, 550 MHz 256 for each server. 10 Gigabytes for each server.

The Microsoft suggested hardware capacity for publishing your internal servers:



Less than 800 Pentium II, 300 Megahertz (MHz)
Approximately 800 Pentium III, 550 MHz
More than 800 Pentium III, 550 MHz. For each 800 hits per second, add an ISA Server computer or add more processors to the ISA Server computer.

ISA Server Operating Modes


Firewall Mode

Cache Mode

Integrated Mode

Enterprise policy Yes Yes YES
Access policy Yes HTTP only YES
Web publishing Yes Yes YES
Server publishing Yes No YES
Packet filtering Yes No YES
Cache configuration No Yes YES
Application filters Yes No YES
Web filters Yes Yes YES
Real-time monitoring Yes Yes YES
Alerts Yes Yes YES
Reports Yes Yes YES
Virtual private networking Yes No YES
SecureNAT client support Yes No YES
Firewall client support Yes No YES
Web Proxy client support Yes Yes YES

ISA Client Types

This information is provided by the ISA Server documentation:


SecureNAT client

Firewall client

Web Proxy client

Installation required Some network configuration changes are required Yes No, requires Web browser configuration
Operating system support Any operating system that supports TCP/IP Only Windows platforms All platforms, but by way of Web application
Protocol support Requires application filters for multi-connection protocols All Winsock applications HTTP



User-level authentication Some network configuration changes are required Yes Yes
Server applications No configuration or installation required Requires configuration file N/A

The following information is extracted from the author Michael Yu Chak Tin's SANS GCFW practical. His entire posted practical is available soon for download at

What is Microsoft ISA Server?

According to Microsoft,

"Microsoft Internet Security and Acceleration (ISA) Server 2000 is an extensible enterprise firewall and Web cache server that integrates with the Microsoft Windows 2000 operating system for policy-based security, as well as accelerating and managing internetworking. ISA Server provides two tightly integrated modes-a multilayer firewall and a high-performance Web cache server. The firewall provides filtering at the packet, circuit, and application layer, stateful inspection to examine data crossing the firewall, control of access policy, and routing of traffic. The cache improves network performance and enhances the end-user experience by storing frequently requested Web content. The firewall and cache can be deployed separately on dedicated servers or integrated on the same computer."

The reason ISA Server is deployed in a network can include:

n          enhance performance - it can act as a proxy caching server for the internal clients, thus enhancing the client's internet browsing performance

n          protect - it has advanced stateful inspection technology for protecting the network

n          publish - reverse proxying and protection for the internal servers

Windows 2000 Installation for ISA Server

First of all, install the latest service pack. At the time of this writing, SP2 is the latest available version. In fact, ISA will not install unless you have applied SP1 at the least.

Microsoft offers Windows 2000 service packs via this URL:

Additionally, the security updates available at should be applied.

Hardening the Configuration

ISA Server includes a Security Configuration Wizard for hardening the Windows 2000 installation. Before invoking ISA for this purpose, apply all the available service packs and updates.

Available at,

"Internet Security and Acceleration (ISA) Server 2000 Service Pack 1 (SP1) provides the latest updates to ISA Server and provides an even higher level of reliability and stability to customers. Microsoft strongly encourages customers to install SP1 on all computers running ISA Server."

According to Microsoft, ISA Server SP1 includes all hot fixes issued since ISA Server was released to manufacturing, fixes for common issues reported by customers through Microsoft Product Support Services (PSS) as well as fixes recommended through an audit by third-party security experts.

Once the service pack is applied, we can invoke the Security Configuration Wizard and start hardening Windows 2000 Server. Of the three different security levels, choose "Dedicated" to produce the most secure firewall system.

The Proxy and Caching functions

A proxy server is a server that sits between a client application and a real server that intercepts all requests to the real server to see if it can fulfill the requests itself. As described by, proxy servers have two main purposes:

"Improve Performance: Proxy servers can dramatically improve performance for groups of users. This is because it saves the results of all requests for a certain amount of time. Consider the case where both user X and user Y access the World Wide Web through a proxy server. First user X requests a certain Web page, which we'll call Page 1. Sometime later, user Y requests the same page. Instead of forwarding the request to the Web server where Page 1 resides, which can be a time-consuming operation, the proxy server simply returns the Page 1 that it already fetched for user X. Since the proxy server is often on the same network as the user, this is a much faster operation. Real proxy servers support hundreds or thousands of users. The major online services such as Compuserve and America Online, for example, employ an array of proxy servers.

Filter Requests: Proxy servers can also be used to filter requests. For example, a company might use a proxy server to prevent its employees from accessing a specific set of Web sites."   

Policy Confusion

ISA Server supports dynamic filtering, meaning ports are opened and closed on an on-demand basis. At the same time, ISA Server supports packet filtering, which is static in nature. So, what is the difference? Somehow most ISA Server documentations out there fail to clearly explain the difference.

In fact, ISA Server provides security via the following means:

n          Access Policy -> Protocol Rules - allow internal client access to the Internet. This is dynamic in nature.

n          Access Policy -> Packet filtering rules - open or close port statically.

n          Publishing Rules - allow external clients access to internal servers. This is dynamic in nature as well.

Basic Caching Options

The default cache size is 100MB. This may not be enough. The factors to consider include the number of users and the frequency of use.


Keep in mind, the construction of this LAT (Local Address table) is very important, as ISA Server relies solely on it to distinguish between trusted nodes and untrusted nodes. If there are changes to the IP address settings, this LAT must be reconstructed. And since the construction of LAT relies heavily on information provided by the routing table, you must ensure that there is no invalid routing entry. Using automatic mechanism like RIP eliminates the need for manually changing the routing table.


Only include the local interface in the LAT. Do not include the internet interface, or ISA will mis-behave.

The internal clients should be properly defined as client sets.

Protocol Rules

Protocol rules in ISA Server determine which protocols clients can use to access the internet. The protocols that the users use must be carefully selected. Rules are applied to allow outbound requests only on these protocols. 

These protocols are application specific. For example, AOL Messenger and ICQ use different protocols. Whether or not these applications are allowed is a matter of company policy.

Firewall Configuration Options

ISA Server relies on packet filtering for its firewall functionalities. Packet filtering, intrusion detection and IP routing can be enabled. To be secure, all packet filtering and intrusion detection related options should be enabled as well.

For packet filtering, the single most important setting is to deny any requests towards the internal network made by any outside parties. Absolutely no connection initiated from the outside! This can be done by creating "block filter" that stop the external hosts from sending packets to all ports on the ISA Server computer.

Since your internal clients may be acting as remote VPN clients for accessing the partners' VPN servers, outgoing PPTP traffic should be allowed to pass through the firewall.

Advanced Caching Options

To allow room for scalability, multiple ISA servers can be chained to form a larger caching mechanism. You can determine if you should ensure that all requests are immediately routed to the destinations rather than to any upstream cache servers, and whether the HTTP / SSL protocols should be transformed into another format when the requests are processed by ISA server.

ISA Server supports two major types of caching: HTTP and FTP. There is always a tradeoff between network traffic and content updates. If the cached objects are to be kept in the cache for a longer period of time, performance will increase because less outgoing traffic is required. However, the cached objects may become outdated. The settings can be adjusted in the form of TTL. As described by,

"Short for Time to Live, (TTL is) a field in the Internet Protocol (IP) that specifies how many more hops a packet can travel before being discarded or returned."

As mentioned before, cached objects may be outdated. For certain objects that involve dynamic contents, caching can be a bad idea. Therefore, do not enable the option "Cache Dynamic Content" for very dynamic contents.

A default configured ISA server will listen on TCP port 8080 as well as SSL port 8443 (SSL port listener must be manually enabled) for outgoing requests. The clients must be configured to forward requests to these ports of the ISA Server's internal interface.

Proxy Filters

You may prevent unauthorized users to access your proxy ports by configuring input filters to allow connections to be made to TCP 8080 and 8443 only from you're your internal clients. You do want to ensure that no one from the outside can make use of your proxy functions.

Web Publishing

Web publishing rules

n          determine how ISA Server should intercept incoming requests for HTTP objects on an internal Web server

n          determine how ISA Server should respond on behalf of the Web server

n          all requests are forwarded downstream to the internal Web server behind the ISA Server

n          internal Web server cannot require digest or basic authentication or the internal name and IP address of the Web server may be exposed

Destination sets and client sets

n          destination sets usually include the external name of your ISA Server computer

n          client address sets should include IP addresses of clients located on the Internet


n          request can be:

u        honored

u        discarded

u        redirected to an alternate site


n          determine how SSL requests should be redirected:

u        as HTTP requests

u        as SSL requests

n          when requests are redirected as SSL requests, the redirection is referred to as SSL bridging

n          You can secure HTTP communication by having it redirected using SSL

n          You can configure HTTP or SSL requests to be passed on as an FTP request to the internal Web server

Rule processing

n          Web publishing rules are processed in order

n          If no rule matches, ISA Server processes the default rule

n          The default rule is configured to discard all requests

n          The default rule is last in the order


Port Settings

To be able to properly protect the network without restricting the functionality, you must know the types of traffic in the network.

You must be able to tell what port to block or allow when the exam question asks you to watch out for a particular problematic application.

The list below is provided by Microsoft at :

Service Name



Browsing datagram responses of NetBIOS over TCP/IP 138  
Browsing requests of NetBIOS over TCP/IP 137  
Client/Server Communication   135
Common Internet File System (CIFS) 445 139, 445
Content Replication Service   560
Cybercash Administration   8001
Cybercash Coin Gateway   8002
Cybercash Credit Gateway   8000
DCOM (SCM uses udp/tcp to dynamically assign ports for DCOM) 135 135
DHCP client   67
DHCP server   68
DHCP Manager   135
DNS Administration   139
DNS client to server lookup (varies) 53 53
Exchange Server 5.0    
   Client Server Communication      135
   Exchange Administrator      135
   IMAP      143
   IMAP (SSL)      993
   LDAP      389
   LDAP (SSL)      636
   MTA - X.400 over TCP/IP      102
   POP3      110
   POP3 (SSL)      995
   RPC      135
   SMTP      25
   NNTP      119
   NNTP (SSL)      563
File shares name lookup 137  
File shares session   139
FTP   21
FTP-data   20
HTTP   80
HTTP-Secure Sockets Layer (SSL)   443
Internet Information Services (IIS)   80
IMAP   143
IMAP (SSL)   993
IKE (For more information, see Table C.4) 500  
IPSec Authentication Header (AH) (For more information, see Table C.4)    
IPSec Encapsulation Security Payload (ESP) (For more information, see Table C.4)    
IRC   531
ISPMOD (SBS 2nd tier DNS registration wizard)   1234
Kerberos de-multiplexer   2053
Kerberos klogin   543
Kerberos kpasswd (v5) 464 464
Kerberos krb5 88 88
Kerberos kshell   544
L2TP 1701  
LDAP   389
LDAP (SSL)   636
Login Sequence 137, 138 139
Macintosh, File Services (AFP/IP)   548
Membership DPA   568
Membership MSN   569
Microsoft Chat client to server   6667
Microsoft Chat server to server   6665
Microsoft Message Queue Server 1801 1801
Microsoft Message Queue Server 3527 135, 2101
Microsoft Message Queue Server   2103, 2105
MTA - X.400 over TCP/IP   102
NetBT datagrams 138  
NetBT name lookups 137  
NetBT service sessions   139
NetLogon 138  
NetMeeting Audio Call Control   1731
NetMeeting H.323 call setup   1720
NetMeeting H.323 streaming RTP over UDP Dynamic  
NetMeeting Internet Locator Server ILS   389
NetMeeting RTP audio stream Dynamic  
NetMeeting T.120   1503
NetMeeting User Location Service   522
NetMeeting user location service ULS   522
Network Load Balancing 2504  
NNTP   119
NNTP (SSL)   563
Outlook (see for ports)    
Pass Through Verification 137, 138 139
POP3   110
POP3 (SSL)   995
PPTP control   1723
PPTP data (see Table C.4)    
Printer sharing name lookup 137  
Printer sharing session   139
Radius accounting (Routing and Remote Access) 1646 or 1813  
Radius authentication (Routing and Remote Access) 1645 or 1812  
Remote Install TFTP   69
RPC client fixed port session queries   1500
RPC client using a fixed port session replication   2500
RPC session ports   Dynamic
RPC user manager, service manager, port mapper   135
SCM used by DCOM 135 135
SMTP   25
SNMP 161  
SNMP Trap 162  
SQL Named Pipes encryption over other protocols name lookup 137  
SQL RPC encryption over other protocols name lookup 137  
SQL session   139
SQL session   1433
SQL session   1024 - 5000
SQL session mapper   135
SQL TCP client name lookup 53 53
Telnet   23
Terminal Server   3389
UNIX Printing   515
WINS Manager   135
WINS NetBios over TCP/IP name service 137  
WINS Proxy 137  
WINS Registration   137
WINS Replication   42
X400   102

Reference Books

MCSE Training Guide (70-227): Installing, Configuring, and Administering Microsoft Internet Security and Acceleration (ISA) Server 2000

By Roberta Bragg; Hardcover

MCSE ISA Server 2000 Exam Cram (Exam: 70-227)

By Diana Bartley, Gregory Smith; Paperback

MCSE: ISA Server 2000 Administration Study Guide: Exam 70 227 with CDROM

By William Heldman; Hardcover

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