How do those hacking tools work? The Art of Port Scanning

nmap
portscanning

(pico) #1

LEVEL: Beginner

Port scanning is the process of finding out which ports are open in a given machine. An open port usually means a program listening on that port, and a program means bugs, and bugs means exploits… roughly :).

OK, everybody in the world uses nmap for this task. It would be stupid to write your own port scanner when such an advanced and polished tool is available. However, knowing how nmap does its magic and also, why not?, write your own simple scanner just for fun, are two valuable learning activities.

In this paper we are going to explore the first one. To get to know how does nmap works. No, no. This is not the typical list of command line flags. We are going to dive into the TCP/IP protocols and understand what is going on under the hood.

Why port scanning is sometimes tricky?

Actually, it is not tricky when doing a legit scanning. Some times you have to scan your own network to debug some problem. In those cases, scanning is pretty simple, you can basically do it with netcat and its -z flag. The process becomes tricky when the scan happens in the frame of an illegal activity, or as part of a security audit of some system.

In this context there are two main reasons that makes the process complicated:

  1. The attacker does not want the victim machine administrator’s to know she is scanning the machine.
  2. The victim machine’s administrators want to minimise the chances of an attack and therefore they will set up firewalls and IDS/IPS systems to avoid such an attach… what includes the recognisance phase.

Because of these two reasons, tools like nmap provides multiple ways to check whether a port is open, and therefore find a potential vulnerable program behind that port.

So, let’s learn the Rules of Port Scanning

The Rules of Port Scanning

Despite of how sophisticated these scans may look, all of them follow some very basic rules and a few exception to those rules… There are always exceptions. So, the Rules of the Port Scanning are:

  • Rule 1. A packet sent to a machine that does not exist will produce as response an ICMP packet indicating that situation
  • Rule 2. A packet sent to a closed port will produce as response an ICMP packet indicating that (UDP) or a RST packet (TCP)
  • Rule 3. A malformed/illegal packet will produce as response a RST packet
  • Rule 4. A filtered port will produce as response an ICMP packet or no response at all (Usually the latest)

Yes, this is it. We will go through the main nmap scanning modes and we will check how all of them resolve to these rules (plus some exceptions to the rules :).

Note that, port scanning only makes sense on transport protocol… protocols with ports. So you can port scan a machine for TCP or UDP services… Therefore, to follow the rest of this paper we will have to take a look to the TCP protocol. In principle, it is not necessary to fiddle with IP, except for the idle scan. Discussing TCP scans will be long enough so I think we will leave UDP for later… or even better for you, dear reader, to research.

Furthermore, nmap provides quite some types of TCP scans. I’m not going to describe all of them, but I will try to provide you with the basic background to further explore those scans on your own.

A TCP Packet

The first thing you need to know, is that, the TCP protocol is described by RFC 793 (http://www.rfc-editor.org/rfc/rfc793.txt). Open the link and go to section 3.1 to see how a TCP packet looks like… OK, you lazy reader, here you go:

 0                   1                   2                   3   
    0 1 2 3 4 5 6 7 8 9 0 1 2 3 4 5 6 7 8 9 0 1 2 3 4 5 6 7 8 9 0 1 
   +-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+
   |          Source Port          |       Destination Port        |
   +-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+
   |                        Sequence Number                        |
   +-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+
   |                    Acknowledgment Number                      |
   +-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+
   |  Data |           |U|A|P|R|S|F|                               |
   | Offset| Reserved  |R|C|S|S|Y|I|            Window             |
   |       |           |G|K|H|T|N|N|                               |
   +-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+
   |           Checksum            |         Urgent Pointer        |
   +-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+
   |                    Options                    |    Padding    |
   +-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+
   |                             data                              |
   +-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+

This is it. Most of the scanning techniques will fiddle with the flags in the fourth row: URG, ACK, PSH, RST, SYN and FIN.

If you already know the basics about TCP internals, you can move on, otherwise, here are a couple of concepts that you need to know.

Three-way handshake

This is how the TCP connection process is usually named (check section 3.4 in the RFC). It requires the transmission of three packets (that’s the three-way in the name…). So, when you try to connect to a TCP server (and this is what the port scanner will be doing all the time), your program will call the connect syscall, and that will fire this process inside the kernel… actually in the TCP/IP stack implementation of the kernel.

  1. The machine that starts the connection will send a SYN packet. This is a packet with the SYN flag (find it in the 4th row in the figure above) set to 1, a random sequence number and proper values for the port fields…
  2. The target machine, supposing that there is a program that had run the listen and accept system calls, will receive the packet and send a SYN/ACK packet back (this is done by the kernel). This packet has the flags SYN and ACK set to 1, a new random sequence number and the sequence number received in the SYN packet copied in the field ACK number and increased by 1.
  3. To complete the process the machine that started the connection has to send another ACK packet to the remote machine with updated sequence numbers.

Let’s duplicate here the nice diagram with real numbers from the RFC

TCP A                                                TCP B

  1.  CLOSED                                               LISTEN

  2.  SYN-SENT    --> <SEQ=100><CTL=SYN>               --> SYN-RECEIVED

  3.  ESTABLISHED <-- <SEQ=300><ACK=101><CTL=SYN,ACK>  <-- SYN-RECEIVED

  4.  ESTABLISHED --> <SEQ=101><ACK=301><CTL=ACK>       --> ESTABLISHED

  5.  ESTABLISHED --> <SEQ=101><ACK=301><CTL=ACK><DATA> --> ESTABLISHED

Talking, Hanging up and Responding to the Unexpected

Once the connection is established, whenever the programs in both ends execute a write/send or read/recv system call, the TCP/IP stack in the kernel will put your data in the Data block (the last row in our TCP packet diagram), and update the sequence numbers accordingly.

The packet will be stored in the kernel (after sending it out), until the other end sends an ACK packet with an acknowledge number higher that the packet sequence number. In other words, the packet will be stored until the other ends indicates that it has received it. Well, this, together with other features (sliding windows algorithm, congestion control, etc…) is what give to TCP its ‘reliability’ feature.

Connection are finished using the FIN flag and here, again there are quite some different cases. You can read the RFC for further details, for our current discussion we just need to know that the FIN flag is used to close a connection.

This is how it works in the nominal case. However, if a strange or unexpected packet is received, the TCP/IP stack will drop that packet and, in general, send back a RST (reset) packet to let the other end know that its packet was discarded.

This is roughly it. Let’s go now into the scanning process.

Understanding ICMP

The other protocol involved in the port scanning process is ICMP, the Internet Control Message Protocol. This is a network protocol that sits besides IP intended to interchange control messages between machines. It is specified in RFC 792 (https://tools.ietf.org/html/rfc792). The format is shown below:

0                   1                   2                   3
0 1 2 3 4 5 6 7 8 9 0 1 2 3 4 5 6 7 8 9 0 1 2 3 4 5 6 7 8 9 0 1
   +-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+
   |     Type      |     Code      |          Checksum             |
   +-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+
   |                             unused                            |
   +-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+
   |      Internet Header + 64 bits of Original Data Datagram      |
   +-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+

ICMP can send messages of a specified Type and, for each type of message, you can also specify a code. There are many different types of messages, but the ones we are interested on are theType 3: Destination Unreachable.

This message can contain the following codes:

  0 = net unreachable;
  1 = host unreachable;
  2 = protocol unreachable;
  3 = port unreachable;
  4 = fragmentation needed and DF set;
  5 = source route failed.

You can see many interesting codes in this list. These messages are generated at different points in the network. Some examples

  • If you computer does not know how to send data to a given host or net (your network configuration is broken or your network is isolated), it will produce the ICMP packet.
  • If you host believe it can send the packet, but your router/gateway finds out it cannot, it may also generate a ICMP message for you. Our packet have not even leave our local network
  • If our make make it up to the remote network, but then the remote router/gateway/firewall determines that the machine does not exist (or is not up) it will produce the ICMP packet
  • If our packet make it up to the final host through the whole Internet, but the UDP port we are trying to reach does not have any program listening, the remote host will generate the ICMP packet. (For a TCP we will get a RST packet instead)

So, as you can see, the ICMP protocol really lives at the network level. Those messages can be generated at any point in the network. From the point of view of the port scanner, it does not really matter who has generated the message, it just needs to capture it and properly interpret it.

Now that we know the low level details, let’s see what happens every time you run nmap.

TCP Connect Scanning

The TCP connect scanning is the simplest one. The scanner just tries to establish a normal connection, calling connect. If connect succeeds (the three-way handshake is completed) the port is open, otherwise the port is closed. The advantage of this scanning technique is that you do not need root privileges to perform it. We are trying to establish normal connection and that does not require special privileges.

The downside is that it is very noisy. Any decent firewall out there will log the connection attempt and, if many connections attempts happens in a short period of time, it will also know that the machine is being scanned.

TCP SYN Scan

If we look to the three-way handshake process, we will notice that it is possible to know if the port is open before the handshake is completed. We just need to send a SYN packet (that gives the name to this scan) and check what we get back:

  • If we get back a normal SYN/ACK packet, then the port is open and we are done
  • If we get back a RST packet, that means the port is closed (Rule 2)
  • If no response or a ICMP unreachable (type 3) port is received then the port is filtered. A firewall is dropping our SYN packet and we are not getting any response back at all (Rule 1, Rule 4)

This scan is also easily detected but usually not by default. On top of that, this is a lot faster that a connect scan as only one packet has to be sent.

This scan does not help when the target is behind a firewall. Usually firewalls block any connection attempt (SYN packets) from outside (unless it is against one of the publicly provided services), that means that a scan against a machine behind a firewall will result in a quite slow scan reporting all ports as filtered. This means that no reply whatsoever was received for the sent packet and our scanner time-out expired for each connection try.

NULL, FIN and Xmas Scans

All these scans are basically the same, the only difference between them is the set of TCP flags in the packet being sent by the scanner. A NULL scan, sets all flags to 0, a FIN scan just sets the FIN flag, and a Xmas (tree) scan set all the TCP flags. nmap actually allows you to provide your own flag pattern if you want to.

All those scans work based on a TCP behaviour described in the RFC. According to the RFC, if a packet reaches a closed port and the packet does not contain a RST, a RST response has to be sent back. In the same section, it is also explained that any packet without the SYN, RST or ACK flags set, send to an open port will force the machine to drop the packet.

So, these scans are intended to differentiate between open and close ports.

This is a very stealthy scan (no connection attempt) but, as usual, modern IDS/IPS can be configured to detect them. The main drawback is that some systems are not compliant with the TCP RFC (RFC 793) and therefore, the scan does not work (the RST packet is not sent back).

These scans are useful to get information on services behind some firewall or packet filter in the target network. This scan can be used to determine which ones of the filtered ports (reported by, for instance, a SYN scan) are actually closed and which ones are open.

ACK Scan

The ACK scan is the latest we are going to describe. This one is special as it is not intended to find open ports but to map firewall rules.

Firewalls are quite complex nowadays and they can work at different levels. A traditional classification of firewalls is stateful and non-stateful. A stateful firewall keeps track of the connections taking place through it. When a connection is established, the firewall note that down and, from that point on, it will drop any packet that does not belong to one of those connections.

This means that, if we send an ACK packet to a port behind a stateful firewall, the packet will be dropped or an ICMP packet type 3 will be generated, because that packet does not belong to any on-going connection. For non-stateful firewalls, the packet will pass through and the remote machine will respond with an RST as the ACK packet will not contain a valid sequence number and it will be identified as not belonging to an existing connection.

So, an ACK scan is intended to figure out if the firewall protecting the victim machine is behind a stateful firewall or not. Well, it can be used for that.

Other Scans

nmap provides other scan types, namely TCP Window scan, Maimon scan, Idle scan,… You can check the man page for nmap to check the complete list and a very comprehensive explanation of how they work. I hope that with our discussion so far you have now the tools to figure out how those scans works. Otherwise, do not hesitate to ask in the comments.

By now, you may know that the scanning process is not that straight forward. It is not just about running a program that will tell you which ports are open, sometimes it becomes more sophisticated and you have to do some thinking on what is going on.

To finish with this paper, I will just describe the general programming elements you may need to build your own Port Scanner. As I said at the beginning if you have a chance to use nmap it is not wise to use your own tool, but, you never know when you may need to write some small tool for a very specific case for which nmap is not an option… (maybe running a scan from a small router??)

Programming a Scanner

Programming a scanner is a very interesting topic because it implies hooking deep into the TCP/IP stack and learn a lot on how the stack really works. Basically you need to do two things:

  1. Craft special packets. You cannot generate this packets using a normal socket
  2. Capture the returned traffic to determine the outcome of the sent packet.

Both tasks requires root privileges, because both tasks requires the use of sockets RAW (man 7 raw). Actually, it is a nice exercise to write your port scanner using sockets RAW directly as that is the lower level you can reach at user space… Then, only the kernel is left. However, tools like nmap does not do that, they use well-known libraries as libpcap for capturing packets and libdnet for crafting packets.

Are you curious why those libraries are used?. Grab the code and take a look. You will see a lot of conditional blocks for different system. Each operating systems, when working at this level, has its own peculiarities and it is quite a work to write code that works on all of them. When you target a specific platform you can write shorter code for it but such a code will not be the most portable in the world. On top of that, a lot of very smart people have worked on these libraries for years and, let’s face it, you think you can do better?..

The libdnet library provides a convenient interface to build any kind of packet. You can easily build any of the packets we had discussed in previous sections, setting flags, ports and sequence numbers.

The libpcap library provides a convenient interface to capture packets. The scanner will have to capture TCP/UDP packets as response from the remote system (RST packets mainly) but it will also have to capture the ICMP messages that will come as response to those packets and that contains valuable information about the state of the port.

Conclusions

Hope this text have given you a more clear understanding of what a port scanner does and how does it work, and how the process itself is not as simple as running a tool, and what are all those scan types for.

I also hope you have grasped what is happening under the hood every time you send some data through the Internet.

Finally, I strongly recommend to read the nmap man page (or the web pages, they contain the same information). It contains a lot of details and a very good description on how this amazing tool does its work.


Remote Shells Part IV. The Invisible Remote Shell
Wannabe Tutorials: Section 2 Part 1
Whats the most anonymous active scanning technique?
#2

Loved the article! Thanks for the info!


#3

Someone has to check your passport because you are from another planet mate.


(Command-Line Ninja) #4

Oh man Pico! You are killing it with content lately! Nice job!


(Not a N00b, but still learning) #5

I think Wireshark would also be a good fit in your series :slight_smile:


(pico) #6

Sure, sniffers will come… actually in two different flavors


(The Defalt) #7

What language do you plan on building these scanners in. If I may suggest, Python has an excellent packet crafting library named Scapy.

-Defalt


(oaktree) #8

@Defalt: @0x00pf likes Lua a lot.


(pico) #9

@Defalt, I know. I have read your great posts.

I think it would depend on how much time I can spend of this. I will definitely talk about libpcap as all my post are C related. Let me know if you have plans to write something on that line so we do not duplicate efforts. I think it will be nice to have different views of the same topic.


(The Defalt) #10

I’ve been studying Java recently, so there shouldn’t be any duplicate content.


#11

Hell Yeah!! I wasnt probably here when this was submitted, but its great, i think i gotta spider the site a bit :wink:.


(Command-Line Ninja) #12

Use Pupper! You can modify it to download the whole site if you so wish :wink:

If anything; the pupper script is better than straight up scraping. Theres a discourse api.


(Valentine) #13

Nice paper. Mind if I reference this paper in my Wannabe Series?

All in all, nice.

Cheers.


#14

Four words : In RFC we trust

Good job mate !


(pico) #15

Sure, use it as it better suits you


(system) #16

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