CompTIA Certifications

CompTIA Network+ 2009 Domain 5: Network Tools

Port Scanner

A port scanner is a tool to scan a server or networking device for open ports. It typically has two uses: for a network administrator to ensure a security policy is properly executed on and for an attacker to probe for an open port to take advantage of.

TCP/IP offers 65536 potential ports for services and applications to communicate on. Typically, an application uses a series of known ports for communication (for example, http uses port 80). A port scanner could examine a series of known ports or just scan a range of ports to discover open ports. A scan on a port generally gives one of three responses:

  1. Open: the host sent a reply indicating it’s listening on that port.
  2. Closed/Denied: the host responded indicating connections on that port will be denied.
  3. Dropped/Blocked: no reply from the host.

Security administrators are most concerned with open ports on applications as there could be a vulnerability and closed ports on operating systems where there could be an exploitation available. Typically, blocked (also known as filtered) ports do not present a security problem.

There are several port scanning types (from Wikipedia):

TCP Scanning

The simplest port scanners use the operating system’s network functions and is generally the next option to go to when SYN is not a feasible option (described next). Nmap calls this mode connect scan, named after the Unix connect() system call. If a port is open, the operating system completes the TCP three-way handshake, and the port scanner immediately closes the connection to avoid performing a kind of Denial-of-service attack. Otherwise an error code is returned. This scan mode has the advantage that the user does not require special privileges. However, using the OS network functions prevents low-level control, so this scan type is less common. This method is “noisy”, particularly if it is a “portsweep“: the services can log the sender IP address and Intrusion detection systems can rise an alarm.

SYN Scanning

SYN scan is another form of TCP scanning. Rather than use the operating system’s network functions, the port scanner generates raw IP packets itself, and monitors for responses. This scan type is also known as “half-open scanning”, because it never actually opens a full TCP connection. The port scanner generates a SYN packet. If the target port is open, it will respond with a SYN-ACK packet. The scanner host responds with a RST packet, closing the connection before the handshake is completed.

The use of raw networking has several advantages, giving the scanner full control of the packets sent and the timeout for responses, and allowing detailed reporting of the responses. There is debate over which scan is less intrusive on the target host. SYN scan has the advantage that the individual services never actually receive a connection while some services can be crashed with a connect scan. However, the RST during the handshake can cause problems for some network stacks, in particular simple devices like printers. There are no conclusive arguments either way.

UDP Scanning

UDP scanning is also possible, although there are technical challenges. UDP is a connectionless protocol so there is no equivalent to a TCP SYN packet. However, if a UDP packet is sent to a port that is not open, the system will respond with an ICMP port unreachable message. Most UDP port scanners use this scanning method, and use the absence of a response to infer that a port is open. However, if a port is blocked by a firewall, this method will falsely report that the port is open. If the port unreachable message is blocked, all ports will appear open. This method is also affected by ICMP rate limiting.

An alternative approach is to send application-specific UDP packets, hoping to generate an application layer response. For example, sending a DNS query to port 53 will result in a response, if a DNS server is present. This method is much more reliable at identifying open ports. However, it is limited to scanning ports for which an application specific probe packet is available. Some tools (e.g., nmap) generally have probes for less than 20 UDP services, while some commercial tools (e.g., nessus) have as many as 70. In some cases, a service may be listening on the port, but configured not to respond to the particular probe packet.

To cope with the different limitations of each approach, some scanners offer a hybrid method. For example, using nmap with the -sUV option will start by using the ICMP port unreachable method, marking all ports as either “closed” or “open|filtered”. The open|filtered ports are then probed for application responses and marked as “open” if one is received.

ACK Scanning

ACK scanning is one of the more unique scan types, as it does not exactly determine whether the port is open or closed, but whether the port is filtered or unfiltered. This is especially good when attempting to probe for the existence of a firewall and its rulesets. Simple packet filtering will allow established connections (packets with the ACK bit set), whereas a more sophisticated stateful firewall might not.

Window Scanning

Rarely used because of its outdated nature, window scanning is fairly untrustworthy in determining whether a port is opened or closed. It generates the same packet as an ACK scan, but checks whether the window field of the packet has been modified. When the packet reaches its destination, a design flaw attempts to create a window size for the packet if the port is open, flagging the window field of the packet with 1’s before it returns to the sender. Using this scanning technique with systems that no longer support this implementation returns 0’s for the window field, labeling open ports as closed.

FIN Scanning

Since SYN scans are not surreptitious enough, firewalls are, in general, scanning for and blocking packets in the form of SYN packets. FIN packets are able to pass by firewalls with no modification to its purpose. Closed ports reply to a FIN packet with the appropriate RST packet, whereas open ports ignore the packet on hand. This is typical behavior due to the nature of TCP, and is in some ways an inescapable downfall. Systems vulnerable to this type of scan are most Unix and NT systems. Microsoft is immune in that it is not bias in the port state and will send a RST packet regardless of the port being open or closed.

On the Network+ Exam

The Network+ exam focuses on the situations you will use a port scanner in the act of troubleshooting your network and in securing your network. For example, if you’re having a problem with your web server serving http traffic, you might use a port scanner to check to see if port 80 is open.