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Before You Begin
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This chapter presents the skills and concepts related to publishing Exchange Server to the Internet. If you plan to complete the practices and lab in this chapter, you should prepare the following:
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A Microsoft Windows Server 2003 (Standard Edition or Enterprise Edition) computer installed as DC1 and configured as a domain controller in the cohovineyard.com domain. A second Windows Server 2003 computer installed as ISA1 and configured as a domain member in the cohovineyard.com domain. This server should have two network interfaces installed. A Windows Server 2003 server installed as MAIL1. This server needs to be a member of the cohovineyard.com domain and have a default installation of Exchange Server 2003 installed on it. The Exchange Server computer requires at least two mailboxes configured on it. A Microsoft Windows Server 2003 (Standard Edition or Enterprise Edition) computer installed as SERVER1. This computer should not be a member of the cohovineyard.com domain. This server should be located on the same network as the external interface of the ISA Server computer. This server should be running the Domain Name System (DNS) Server and the DNS client setting should be configured to use the server s Internet Protocol (IP) address as the DNS server. To complete the Outlook publishing practices, you also need to have a computer running Microsoft Outlook 2003 available on the same network as the external interface of the ISA Server computer. You can run Outlook 2003 on SERVER1 or, if you have Outlook 2003 installed on CLIENT1, you can configure the IP address for CLIENT1 so that it is on the external network.
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Lesson 1
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Configuring ISA Server to Secure SMTP Traffic
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Lesson 1: Configuring ISA Server to Secure SMTP Traffic
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One way that ISA Server can secure Exchange Server is by providing enhanced options for filtering all SMTP messages sent from the Internet to the computers running Exchange Server. This lesson explains how to publish SMTP servers and how to configure SMTP filtering.
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After this lesson, you will be able to
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Describe known SMTP messaging security issues Implement ISA Server to secure SMTP traffic Configure SMTP application filter Implement SMTP Message Screener Plan an SMTP Message Screener implementation
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Estimated lesson time: 40 minutes
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Known SMTP Security Issues
Virtually all e-mail sent on the Internet is sent using SMTP. To receive e-mail from the Internet, your organization must have an SMTP server that is accessible to other SMTP servers. However, SMTP has some security weaknesses, both at a protocol level and in terms of the content sent using SMTP messages.
SMTP Protocol-Level Exploits
SMTP servers are vulnerable to several protocol level exploits including buffer-overflow attacks and SMTP command attacks. Buffer-overflow attacks A buffer-overflow attack is triggered when a program or process tries to store more data in a memory buffer than the buffer s designed capacity. The extra information can spill into adjacent buffers, corrupting or overwriting the valid data that they hold. In buffer-overflow attacks, the extra data may contain code designed to trigger specific actions, in effect sending new instructions to the attacked computer. Buffer-overflow attacks can be mounted against an organization s SMTP server by sending large SMTP commands. The best deterrent to a buffer-overflow attack against the SMTP server is to stop the attacker at the network perimeter, before the exploit ever finds its way into the corporate network. Attackers use buffer-overflow exploits to disable specific server services with the intent of mounting a denial-of-service (DoS) attack, either by disabling a specific service on the target computer or by taking the entire machine offline. More elaborate bufferoverflow exploits can be used to disable key security features and allow the attacker to run commands of his choice on the targeted machine.
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Integrating ISA Server 2004 and Exchange Server
Important These SMTP vulnerabilities are well known, and most SMTP servers are either not vulnerable to the exploits or can be patched so that they are not vulnerable. However, ISA Server can block the attack at the network perimeter so that the attack does not reach the SMTP server.
SMTP command attacks SMTP servers must support a standard set of commands that are used to send and receive SMTP messages. Attackers can use the commands to mount buffer-overflow attacks or to send malformed commands that the system programmers did not anticipate. Command-manipulation attacks can lead to system compromise by giving an attacker access to key files, the ability to overwrite files, or to inject Trojan horse programs onto a mail server. Some SMTP commands are optional. Some commands, such as EXPN and VRFY, if configured incorrectly, can be used to find a list of recipients on the server. If these commands are not required, they can be disabled at the firewall so that the SMTP server does not receive them.
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