Cyber Security

How To Manage Email Security

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Email is one of the most widely and commonly used Internet services. The email infrastructure employed on the Internet primarily consists of email servers using Simple Mail Transfer Protocol (SMTP) to accept messages from clients, transport those messages to other servers, and deposit them into a user’s server-based inbox.

In addition to email servers, the infrastructure includes email clients. Clients retrieve email from their serverbased inboxes using Post Office Protocol version 3 (POP3) or Internet Message Access Protocol (IMAP). Clients communicate with email servers using SMTP. Many Internetcompatible email systems rely on the X.400 standard for addressing and message handling. Sendmail is the most common SMTP server for Unix systems and Exchange is the most common SMTP server for Microsoft systems. In addition to these three popular products, numerous alternatives exist, but they all share the same basic functionality and compliance with Internet email standards.

If you deploy an SMTP server, it is imperative that you properly configure authentication for both inbound and outbound mail. SMTP is designed to be a mail relay system. This means it relays mail from sender to intended recipient. However, you want to avoid turning your SMTP server into an open relay (also known as an open relay agent or relay agent), which is an STMP server that does not authenticate senders before accepting and relaying mail. Open relays are prime targets for spammers because they allow spammers to send out floods of emails by piggybacking on an insecure email infrastructure. As open relays are locked down, becoming closed or authentication relays, a growing number of SMTP attacks are occurring through hijacked authenticated user accounts.

Email Security Goals

For email, the basic mechanism in use on the Internet offers the efficient delivery of messages but lacks controls to provide for confidentiality, integrity, or even availability. In other words, basic email is not secure. However, you can add security to email in many ways. Adding security to email may satisfy one or more of the following objectives:

Provide for nonrepudiation
Restrict access to messages to their intended recipients (i.e., privacy and confidentiality)
Maintain the integrity of messages
Authenticate and verify the source of messages
Verify the delivery of messages
Classify sensitive content within or attached to messages

Acceptable use policies for email
Access control Privacy
Email management
Email backup and retention policies

Acceptable use policies define what activities can and cannot be performed over an organization’s email infrastructure. It is often stipulated that professional, businessoriented email and a limited amount of personal email can be sent and received. Specific restrictions are usually placed on performing personal business (that is, work for another organization, including self-employment) and sending or receiving illegal, immoral, or offensive communications as well as on engaging in any other activities that would have a detrimental effect on productivity, profitability, or public relations.

Access control over email should be maintained so that users have access only to their specific inbox and email archive databases. An extension of this rule implies that no other user, authorized or not, can gain access to an individual’s email. Access control should provide for both legitimate access and some level of privacy, at least from other employees and unauthorized intruders.

The mechanisms and processes used to implement, maintain, and administer email for an organization should be clarified. End users may not need to know the specifics of email management, but they do need to know whether email is considered private communication. Email has recently been the focus of numerous court cases in which archived messages were used as evidence—often to the chagrin of the author or recipient of those messages. If email is to be retained (that is, backed up and stored in archives for future use), users need to be made aware of this. If email is to be reviewed for violations by an auditor, users need to be informed of this as well. Some companies have elected to retain only the last three months of email archives before they are destroyed, whereas others have opted to retain email for years. Depending upon your country and industry, there are often regulations that dictate retention policies.

Understand Email Security Issues

The first step in deploying email security is to recognize the vulnerabilities specific to email. The protocols used to support email do not employ encryption. Thus, all messages are transmitted in the form in which they are submitted to the email server, which is often plain text. This makes interception and eavesdropping easy. However, the lack of native encryption is one of the least important security issues related to email.

Email is a common delivery mechanism for viruses, worms, Trojan horses, documents with destructive macros, and other malicious code. The proliferation of support for various scripting languages, autodownload capabilities, and autoexecute features has transformed hyperlinks within the content of email and attachments into a serious threat to every system.

Email offers little in the way of source verification. Spoofing the source address of email is a simple process for even a novice attacker. Email headers can be modified at their source or at any point during transit. Furthermore, it is also possible to deliver email directly to a user’s inbox on an email server by directly connecting to the email server’s SMTP port. And speaking of in-transit modification, there are no native integrity checks to ensure that a message was not altered between its source and destination.

In addition, email itself can be used as an attack mechanism. When sufficient numbers of messages are directed to a single user’s inbox or through a specific STMP server, a denialof-service (DoS) attack can result. This attack is often called mail-bombing and is simply a DoS performed by inundating a system with messages. The DoS can be the result of storage capacity consumption or processing capability utilization. Either way, the result is the same: Legitimate messages cannot be delivered.

Like email flooding and malicious code attachments, unwanted email can be considered an attack. Sending unwanted, inappropriate, or irrelevant messages is called spamming. Spamming is often little more than a nuisance, but it does waste system resources both locally and over the Internet. It is often difficult to stop spam because the source of the messages is usually spoofed.

Email Security Solutions

Imposing security on email is possible, but the efforts should be in tune with the value and confidentiality of the messages being exchanged. You can use several protocols, services, and solutions to add security to email without requiring a complete overhaul of the entire Internet-based SMTP infrastructure. These include S/MIME, MOSS, PEM, and PGP. We’ll discuss S/MIME further in Chapter 7, “PKI and Cryptographic Applications.”


Secure Multipurpose Internet Mail Extensions (S/MIME)
Secure Multipurpose Internet Mail Extensions is an email security standard that offers authentication and confidentiality to email through public key encryption and digital signatures. Authentication is provided through X.509 digital certificates. Privacy is provided through the use of Public Key Cryptography Standard (PKCS) encryption. Two types of messages can be formed using S/MIME: signed messages and secured enveloped messages. A signed message provides integrity, sender authentication, and nonrepudiation. An enveloped message provides integrity, sender authentication, and confidentiality.

MIME Object Security Services (MOSS) MIME Object Security Services can provide authentication, confidentiality, integrity, and nonrepudiation for email messages. MOSS employs Message Digest 2 (MD2) and MD5 algorithms; Rivest, Shamir, and Adelman (RSA) public key; and Data Encryption Standard (DES) to provide authentication and encryption services.

Privacy Enhanced Mail (PEM) Privacy Enhanced Mail is an email encryption mechanism that provides authentication, integrity, confidentiality, and nonrepudiation. PEM uses RSA, DES, and X.509.

Pretty Good Privacy (PGP) Pretty Good Privacy (PGP) is a public-private key system that uses a variety of encryption algorithms to encrypt files and email messages. The first version of PGP used RSA, the second version, International Data Encryption Algorithm (IDEA), but later versions offered a spectrum of algorithm options. PGP is not a standard but rather an independently developed product that has wide Internet grassroots support.

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