smtp
Last updated
Last updated
What is SMTP?
SMTP stands for "Simple Mail Transfer Protocol". It is utilised to handle the sending of emails. In order to support email services, a protocol pair is required, comprising of SMTP and POP/IMAP. Together they allow the user to send outgoing mail and retrieve incoming mail, respectively.
The SMTP server performs three basic functions:
It verifies who is sending emails through the SMTP server.
It sends the outgoing mail
If the outgoing mail can't be delivered it sends the message back to the sender
POP and IMAP
POP, or "Post Office Protocol" and IMAP, "Internet Message Access Protocol" are both email protocols who are responsible for the transfer of email between a client and a mail server. The main differences is in POP's more simplistic approach of downloading the inbox from the mail server, to the client. Where IMAP will synchronise the current inbox, with new mail on the server, downloading anything new. This means that changes to the inbox made on one computer, over IMAP, will persist if you then synchronise the inbox from another computer. The POP/IMAP server is responsible for fulfiling this process.
How does SMTP work?
Email delivery functions much the same as the physical mail delivery system. The user will supply the email (a letter) and a service (the postal delivery service), and through a series of steps- will deliver it to the recipients inbox (postbox). The role of the SMTP server in this service, is to act as the sorting office, the email (letter) is picked up and sent to this server, which then directs it to the recipient.
We can map the journey of an email from your computer to the recipient’s like this:
1. The mail user agent, which is either your email client or an external program. connects to the SMTP server of your domain, e.g. smtp.google.com. This initiates the SMTP handshake. This connection works over the SMTP port- which is usually 25. Once these connections have been made and validated, the SMTP session starts.
2. The process of sending mail can now begin. The client first submits the sender, and recipient's email address- the body of the email and any attachments, to the server.
3. The SMTP server then checks whether the domain name of the recipient and the sender is the same.
4. The SMTP server of the sender will make a connection to the recipient's SMTP server before relaying the email. If the recipient's server can't be accessed, or is not available- the Email gets put into an SMTP queue.
5. Then, the recipient's SMTP server will verify the incoming email. It does this by checking if the domain and user name have been recognised. The server will then forward the email to the POP or IMAP server, as shown in the diagram above.
6. The E-Mail will then show up in the recipient's inbox.
Poorly configured or vulnerable mail servers can often provide an initial foothold into a network, but prior to launching an attack, we want to fingerprint the server to make our targeting as precise as possible. We're going to use the "smtp_version" module in MetaSploit to do this. As its name implies, it will scan a range of IP addresses and determine the version of any mail servers it encounters.
The SMTP service has two internal commands that allow the enumeration of users: VRFY (confirming the names of valid users) and EXPN (which reveals the actual address of user’s aliases and lists of e-mail (mailing lists). Using these SMTP commands, we can reveal a list of valid users.
It's worth noting that this enumeration technique will work for the majority of SMTP configurations; however there are other, non-metasploit tools such as smtp-user-enum that work even better for enumerating OS-level user accounts on Solaris via the SMTP service. Enumeration is performed by inspecting the responses to VRFY, EXPN, and RCPT TO commands.
we first use smtp_version module of metasploit to find about the mail name and the mail server. then we use smtp_enum to enumerate the smtp server and collect info.
(in this case we got a username and used it to bruteforce the ssh password and gain access to the machine)
