Enumeration

When it comes to hacking, knowledge is power. The more knowledge you have about a target system or network, the more options you have available. This makes it imperative that proper enumeration is carried out before any exploitation attempts are made.

Say we have been given an IP (or multiple IP addresses) to perform a security audit on. Before we do anything else, we need to get an idea of the “landscape” we are attacking. What this means is that we need to establish which services are running on the targets. For example, perhaps one of them is running a webserver, and another is acting as a Windows Active Directory Domain Controller. The first stage in establishing this “map” of the landscape is something called port scanning. When a computer runs a network service, it opens a networking construct called a “port” to receive the connection. Ports are necessary for making multiple network requests or having multiple services available. For example, when you load several webpages at once in a web browser, the program must have some way of determining which tab is loading which web page. This is done by establishing connections to the remote webservers using different ports on your local machine. Equally, if you want a server to be able to run more than one service (for example, perhaps you want your webserver to run both HTTP and HTTPS versions of the site), then you need some way to direct the traffic to the appropriate service. Once again, ports are the solution to this. Network connections are made between two ports – an open port listening on the server and a randomly selected port on your own computer. For example, when you connect to a web page, your computer may open port 49534 to connect to the server’s port 443.

Your computer opens up a different, high-numbered port (at random), which it uses for all its communications with the remote server. You can have many separate ports and connections open at the same time.

Every computer has a total of 65535 available ports; however, many of these are registered as standard ports. For example, a HTTP Webservice can nearly always be found on port 80 of the server. A HTTPS Webservice can be found on port 443. Windows NETBIOS can be found on port 139 and SMB can be found on port 445. It is important to note; however, that especially in a CTF setting, it is not unheard of for even these standard ports to be altered, making it even more imperative that we perform appropriate enumeration on the target.

If we do not know which of these ports a server has open, then we do not have a hope of successfully attacking the target; thus, it is crucial that we begin any attack with a port scan. This can be accomplished in a variety of ways – usually using a tool called nmap.

nmap

Nmap can be used to perform many different kinds of port scan, but the basic theory is this: nmap will connect to each port of the target in turn. Depending on how the port responds, it can be determined as being open, closed, or filtered (usually by a firewall). Once we know which ports are open, we can then look at enumerating which services are running on each port – either manually, or more commonly using nmap.

So, why nmap? The short answer is that it's currently the industry standard for a reason: no other port scanning tool comes close to matching its functionality (although some newcomers are now matching it for speed). It is an extremely powerful tool – made even more powerful by its scripting engine which can be used to scan for vulnerabilities, and in some cases even perform the exploit directly.

Scan Type

When port scanning with Nmap, there are three basic scan types. These are:

• TCP Connect Scans (-sT)

  • Nmap sends a TCP request with the SYN flag set to a closed port, the target server will respond with a TCP packet with the RST (Reset) flag set. By this response, Nmap can establish that the port is closed.

  • If, however, the request is sent to an open port, the target will respond with a TCP packet with the SYN/ACK flags set. Nmap then marks this port as being open (and completes the handshake by sending back a TCP packet with ACK set).

  • What if the port is open, but hidden behind a firewall?

    Many firewalls are configured to simply drop incoming packets. Nmap sends a TCP SYN request, and receives nothing back. This indicates that the port is being protected by a firewall and thus the port is considered to be filtered. This can make it extremely difficult (if not impossible) to get an accurate reading of the target(s).

• SYN "Half-open" Scans (-sS)

• UDP Scans (-sU)

Additionally there are several less common port scan types, some of which we will also cover (albeit in less detail). These are:

• TCP Null Scans (-sN)

• TCP FIN Scans (-sF)

• TCP Xmas Scans (-sX)

Most of these (with the exception of UDP scans) are used for very similar purposes, however, the way that they work differs between each scan. This means that, whilst one of the first three scans are likely to be your go-to in most situations, it's worth bearing in mind that other scan types exist.