Hands on Hacking

Chapter 6Electronic Mail

You have gathered intelligence on your target and investigated DNS services. You will now investigate and hack your way into a mail server, eventually obtaining access to the root user account. Companies may use managed service providers (MSPs), such as Google and Microsoft, or they may use a self-hosted solution. Understanding how a mail server works and how it can be compromised will be invaluable to you as a hacker. Email is one of the primary capabilities of computers, and people have been using computers to send and receive messages ever since they started using them on a network.

The Email Chain

The basic concept of email is simple. First, you write your email using your email client. This could be Google Mail in your web browser, Microsoft Outlook, or another email client, such as Mozilla Thunderbird. These are all mail user agents (MUAs), and this is where the journey of an email begins.

When you hit Send, your email client connects to a mail transfer agent (MTA), which is a different piece of software—for example, Sendmail or Exim—and it usually runs on a remote mail server. Your email is transferred using the Simple Mail Transfer Protocol (SMTP), which we will explore soon. Once the MTA running on the mail server has received your message, it will send it to another MTA, which will eventually pass the email to a message delivery agent (MDA). An MDA is yet another piece of software with the job of actually delivering your email to the recipient's ...