Nmap Commands
Nmap Commands
Listen Share
Learn advanced techniques such as null, FIN, Xmas, and idle (zombie) scans,
spoofing, in addition to FW and IDS evasion.
TASK 1
This room is the third in the Nmap series (part of the Introduction to Network
Security module). In the first two rooms, we learned about live host discovery and
basic port scans.
In Nmap Basic Port Scans, we covered TCP flags and reviewed the TCP 3-way
handshake. To initiate a connection, TCP requires the first packet to have the SYN
flag set. Consequently, we can tell if a TCP port is open based on the response we
receive.
Security researchers and hackers contemplated the TCP flags, shown in the figure
below and explained in the previous room, and started to experiment. They wanted
to know what would happen if we send a TCP packet, which is not part of any
ongoing TCP connection, with one or more flags set.
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For instance, an ACK flag is set when you want to acknowledge received data. An
ACK scan is like trying to acknowledge data that was neither sent nor received in the
first place. Consider this simple analogy, someone coming to you out of nowhere to
tell you, “yes, I hear you, please continue.” when you haven’t said anything.
This room explains advanced types of scans and scan options. Some of these scan
types can be useful against specific systems, while others are useful in particular
network setups. We will cover the following types of port scans:
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Null Scan
Search
FIN Scan
Xmas Scan
Maimon Scan
ACK Scan
Window Scan
Custom Scan
Spoofing IP
Spoofing MAC
Decoy Scan
Fragmented Packets
Idle/Zombie Scan
We will discuss options and techniques to evade firewalls and IDS systems. We also
cover options to get more verbose details from Nmap.
Launch the AttackBox by using the Start AttackBox button and get ready to
experiment with different types of Nmap scans against different virtual machines.
No answer needed
Null Scan
FIN Scan
Xmas Scan
Null Scan
The null scan does not set any flag; all six flag bits are set to zero. You can choose
this scan using the -sN option. A TCP packet with no flags set will not trigger any
response when it reaches an open port, as shown in the figure below. Therefore,
from Nmap’s perspective, a lack of reply in a null scan indicates that either the port
is open or a firewall is blocking the packet.
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However, we expect the target server to respond with an RST packet if the port is
closed. Consequently, we can use the lack of RST response to figure out the ports
that are not closed: open or filtered.
Below is an example of a null scan against a Linux server. The null scan we carried
out has successfully identified the six open ports on the target system. Because the
null scan relies on the lack of a response to infer that the port is not closed, it cannot
indicate with certainty that these ports are open; there is a possibility that the ports
are not responding due to a firewall rule.
Pentester Terminal
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Note that many Nmap options require root privileges. Unless you are running Nmap
as root, you need to use sudo as in the example above using the -sN option.
FIN Scan
The FIN scan sends a TCP packet with the FIN flag set. You can choose this scan type
using the -sF option. Similarly, no response will be sent if the TCP port is open.
Again, Nmap cannot be sure if the port is open or if a firewall is blocking the traffic
related to this TCP port.
However, the target system should respond with an RST if the port is closed.
Consequently, we will be able to know which ports are closed and use this
knowledge to infer the ports that are open or filtered. It’s worth noting some
firewalls will ‘silently’ drop the traffic without sending an RST.
Below is an example of a FIN scan against a Linux server. The result is quite similar
to the result we obtained earlier using a null scan.
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Pentester Terminal
Xmas Scan
The Xmas scan gets its name after Christmas tree lights. An Xmas scan sets the FIN,
PSH, and URG flags simultaneously. You can select Xmas scan with the option -sX .
Like the Null scan and FIN scan, if an RST packet is received, it means that the port
is closed. Otherwise, it will be reported as open|filtered.
The following two figures show the case when the TCP port is open and the case
when the TCP port is closed.
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The console output below shows an example of a Xmas scan against a Linux server.
The obtained results are pretty similar to that of the null scan and the FIN scan.
Pentester Terminal
One scenario where these three scan types can be efficient is when scanning a
target behind a stateless (non-stateful) firewall. A stateless firewall will check if the
incoming packet has the SYN flag set to detect a connection attempt. Using a flag
combination that does not match the SYN packet makes it possible to deceive the
firewall and reach the system behind it. However, a stateful firewall will practically
block all such crafted packets and render this kind of scan useless.
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Start the VM and load the AttackBox. Once both are ready, open the terminal on the
AttackBox and use nmap to launch a FIN scan against the target VM. How many
ports appear as open|filtered?
Repeat your scan launching a null scan against the target VM. How many ports
appear as open|filtered?
Uriel Maimon first described this scan in 1996. In this scan, the FIN and ACK bits
are set. The target should send an RST packet as a response. However, certain BSD-
derived systems drop the packet if it is an open port exposing the open ports. This
scan won’t work on most targets encountered in modern networks; however, we
include it in this room to better understand the port scanning mechanism and the
hacking mindset. To select this scan type, use the -sM option.
Most target systems respond with an RST packet regardless of whether the TCP port
is open. In such a case, we won’t be able to discover the open ports. The figure
below shows the expected behaviour in the cases of both open and closed TCP ports.
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The console output below is an example of a TCP Maimon scan against a Linux
server. As mentioned, because open ports and closed ports are behaving the same
way, the Maimon scan could not discover any open ports on the target system.
Pentester Terminal
This type of scan is not the first scan one would pick to discover a system; however,
it is important to know about it as you don’t know when it could come in handy.
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This task will cover how to perform a TCP ACK scan, a TCP window scan, and how
to create your custom flag scan.
Pentester Terminal
This kind of scan would be helpful if there is a firewall in front of the target.
Consequently, based on which ACK packets resulted in responses, you will learn
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which ports were not blocked by the firewall. In other words, this type of scan is
more suitable to discover firewall rule sets and configuration.
After setting up the target VM MACHINE_IP with a firewall, we repeated the ACK scan.
This time, we received some interesting results. As seen in the console output
below, we have three ports that aren't being blocked by the firewall. This result
indicates that the firewall is blocking all other ports except for these three ports.
Pentester Terminal
Window Scan
Another similar scan is the TCP window scan. The TCP window scan is almost the
same as the ACK scan; however, it examines the TCP Window field of the RST
packets returned. On specific systems, this can reveal that the port is open. You can
select this scan type with the option -sW . As shown in the figure below, we expect to
get an RST packet in reply to our “uninvited” ACK packets, regardless of whether the
port is open or closed.
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Similarly, launching a TCP window scan against a Linux system with no firewall will
not provide much information. As we can see in the console output below, the
results of the window scan against a Linux server with no firewall didn’t give any
extra information compared to the ACK scan executed earlier.
Pentester Terminal
However, as you would expect, if we repeat our TCP window scan against a server
behind a firewall, we expect to get more satisfying results. In the console output
shown below, the TCP window scan pointed that three ports are detected as closed.
(This is in contrast with the ACK scan that labelled the same three ports as
unfiltered.) Although we know that these three ports are not closed, we realize they
responded differently, indicating that the firewall does not block them.
Pentester Terminal
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Custom Scan
If you want to experiment with a new TCP flag combination beyond the built-in TCP
scan types, you can do so using --scanflags . For instance, if you want to set SYN,
RST, and FIN simultaneously, you can do so using --scanflags RSTSYNFIN . As shown
in the figure below, if you develop your custom scan, you need to know how the
different ports will behave to interpret the results in different scenarios correctly.
Finally, it is essential to note that the ACK scan and the window scan were very
efficient at helping us map out the firewall rules. However, it is vital to remember
that just because a firewall is not blocking a specific port, it does not necessarily
mean that a service is listening on that port. For example, there is a possibility that
the firewall rules need to be updated to reflect recent service changes. Hence, ACK
and window scans are exposing the firewall rules, not the services.
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You decided to experiment with a custom TCP scan that has the reset flag set. What
would you add after --scanflags ?
RST
The VM received an update to its firewall ruleset. A new port is now allowed by the
firewall. After you make sure that you have terminated the VM from Task 2, start the
VM for this task. Launch the AttackBox if you haven’t done that already. Once both
are ready, open the terminal on the AttackBox and use Nmap to launch an ACK scan
against the target VM. How many ports appear unfiltered?
443
Is there any service behind the newly discovered port number? (Y/N)
In some network setups, you will be able to scan a target system using a spoofed IP
address and even a spoofed MAC address. Such a scan is only beneficial in a
situation where you can guarantee to capture the response. If you try to scan a target
from some random network using a spoofed IP address, chances are you won’t have
any response routed to you, and the scan results could be unreliable.
The following figure shows the attacker launching the command nmap -S SPOOFED_IP
MACHINE_IP . Consequently, Nmap will craft all the packets using the provided source
IP address SPOOFED_IP . The target machine will respond to the incoming packets
sending the replies to the destination IP address SPOOFED_IP . For this scan to work
and give accurate results, the attacker needs to monitor the network traffic to
analyze the replies.
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1. Attacker sends a packet with a spoofed source IP address to the target machine.
In general, you expect to specify the network interface using -e and to explicitly
disable ping scan -Pn . Therefore, instead of nmap -S SPOOFED_IP MACHINE_IP , you will
need to issue nmap -e NET_INTERFACE -Pn -S SPOOFED_IP MACHINE_IP to tell Nmap
explicitly which network interface to use and not to expect to receive a ping reply. It
is worth repeating that this scan will be useless if the attacker system cannot
monitor the network for responses.
When you are on the same subnet as the target machine, you would be able to spoof
your MAC address as well. You can specify the source MAC address using --spoof-
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mac SPOOFED_MAC . This address spoofing is only possible if the attacker and the target
machine are on the same Ethernet (802.3) network or same WiFi (802.11).
Spoofing only works in a minimal number of cases where certain conditions are
met. Therefore, the attacker might resort to using decoys to make it more
challenging to be pinpointed. The concept is simple, make the scan appear to be
coming from many IP addresses so that the attacker’s IP address would be lost
among them. As we see in the figure below, the scan of the target machine will
appear to be coming from 3 different sources, and consequently, the replies will go
the decoys as well.
You can launch a decoy scan by specifying a specific or random IP address after -D .
ME to indicate that your IP address should appear in the third order. Another
example command would be nmap -D 10.10.0.1,10.10.0.2,RND,RND,ME MACHINE_IP ,
where the third and fourth source IP addresses are assigned randomly, while the
fifth source is going to be the attacker’s IP address. In other words, each time you
execute the latter command, you would expect two new random IP addresses to be
the third and fourth decoy sources.
What do you need to add to the command sudo nmap MACHINE_IP to make the scan
appear as if coming from the source IP address 10.10.10.11 instead of your IP
address?
-S 10.10.10.11
What do you need to add to the command sudo nmap MACHINE_IP to make the scan
appear as if coming from the source IP addresses 10.10.20.21 and 10.10.20.28 in
addition to your IP address?
D 10.10.20.21,10.10.20.28,ME
Firewall
A firewall is a piece of software or hardware that permits packets to pass through or
blocks them. It functions based on firewall rules, summarized as blocking all traffic
with exceptions or allowing all traffic with exceptions. For instance, you might
block all traffic to your server except those coming to your web server. A traditional
firewall inspects, at least, the IP header and the transport layer header. A more
sophisticated firewall would also try to examine the data carried by the transport
layer.
IDS
An intrusion detection system (IDS) inspects network packets for select behavioural
patterns or specific content signatures. It raises an alert whenever a malicious rule
is met. In addition to the IP header and transport layer header, an IDS would inspect
the data contents in the transport layer and check if it matches any malicious
patterns. How can you make it less likely for a traditional firewall/IDS to detect your
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Nmap activity? It is not easy to answer this; however, depending on the type of
firewall/IDS, you might benefit from dividing the packet into smaller packets.
Fragmented Packets
Nmap provides the option -f to fragment packets. Once chosen, the IP data will be
divided into 8 bytes or less. Adding another -f ( -f -f or -ff ) will split the data into
16 byte-fragments instead of 8. You can change the default value by using the --mtu ;
Let’s compare running sudo nmap -sS -p80 10.20.30.144 and sudo nmap -sS -p80 -f
10.20.30.144 . As you know by now, this will use stealth TCP SYN scan on port 80;
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In the first two lines, we can see an ARP query and response. Nmap issued an ARP
query because the target is on the same Ethernet. The second two lines show a TCP
SYN ping and a reply. The fifth line is the beginning of the port scan; Nmap sends a
TCP SYN packet to port 80. In this case, the IP header is 20 bytes, and the TCP
header is 24 bytes. Note that the minimum size of the TCP header is 20 bytes.
With fragmentation requested via -f , the 24 bytes of the TCP header will be divided
into multiples of 8 bytes, with the last fragment containing 8 bytes or less of the TCP
header. Since 24 is divisible by 8, we got 3 IP fragments; each has 20 bytes of IP
header and 8 bytes of TCP header. We can see the three fragments between the fifth
and the seventh lines.
Note that if you added -ff (or -f -f ), the fragmentation of the data will be
multiples of 16. In other words, the 24 bytes of the TCP header, in this case, would
be divided over two IP fragments, the first containing 16 bytes and the second
containing 8 bytes of the TCP header.
On the other hand, if you prefer to increase the size of your packets to make them
look innocuous, you can use the option --data-length NUM , where num specifies the
number of bytes you want to append to your packets.
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If the TCP segment has a size of 64, and -ff option is being used, how many IP
fragments will you get?
The idle scan, or zombie scan, requires an idle system connected to the network
that you can communicate with. Practically, Nmap will make each probe appear as
if coming from the idle (zombie) host, then it will check for indicators whether the
idle (zombie) host received any response to the spoofed probe. This is accomplished
by checking the IP identification (IP ID) value in the IP header. You can run an idle
scan using nmap -sI ZOMBIE_IP MACHINE_IP , where ZOMBIE_IP is the IP address of the
idle host (zombie).
The idle (zombie) scan requires the following three steps to discover whether a port
is open:
1. Trigger the idle host to respond so that you can record the current IP ID on the
idle host.
2. Send a SYN packet to a TCP port on the target. The packet should be spoofed to
appear as if it was coming from the idle host (zombie) IP address.
3. Trigger the idle machine again to respond so that you can compare the new IP
ID with the one received earlier.
Let’s explain with figures. In the figure below, we have the attacker system probing
an idle machine, a multi-function printer. By sending a SYN/ACK, it responds with
an RST packet containing its newly incremented IP ID.
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The attacker will send a SYN packet to the TCP port they want to check on the target
machine in the next step. However, this packet will use the idle host (zombie) IP
address as the source. Three scenarios would arise. In the first scenario, shown in
the figure below, the TCP port is closed; therefore, the target machine responds to
the idle host with an RST packet. The idle host does not respond; hence its IP ID is
not incremented.
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In the second scenario, as shown below, the TCP port is open, so the target machine
responds with a SYN/ACK to the idle host (zombie). The idle host responds to this
unexpected packet with an RST packet, thus incrementing its IP ID.
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In the third scenario, the target machine does not respond at all due to firewall
rules. This lack of response will lead to the same result as with the closed port; the
idle host won’t increase the IP ID.
For the final step, the attacker sends another SYN/ACK to the idle host. The idle host
responds with an RST packet, incrementing the IP ID by one again. The attacker
needs to compare the IP ID of the RST packet received in the first step with the IP ID
of the RST packet received in this third step. If the difference is 1, it means the port
on the target machine was closed or filtered. However, if the difference is 2, it
means that the port on the target was open.
It is worth repeating that this scan is called an idle scan because choosing an idle
host is indispensable for the accuracy of the scan. If the “idle host” is busy, all the
returned IP IDs would be useless.
You discovered a rarely-used network printer with the IP address 10.10.5.5 , and
you decide to use it as a zombie in your idle scan. What argument should you add to
your Nmap command?
-sI 10.10.5.5
You might consider adding --reason if you want Nmap to provide more details
regarding its reasoning and conclusions. Consider the two scans below to the
system; however, the latter adds --reason .
Pentester Terminal
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Pentester Terminal
Providing the --reason flag gives us the explicit reason why Nmap concluded that
the system is up or a particular port is open. In this console output above, we can
see that this system is considered online because Nmap “received arp-response.” On
the other hand, we know that the SSH port is deemed to be open because Nmap
received a “syn-ack” packet back.
For more detailed output, you can consider using -v for verbose output or -vv for
even more verbosity.
Pentester Terminal
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If -vv does not satisfy your curiosity, you can use -d for debugging details or -dd
for even more details. You can guarantee that using -d will create an output that
extends beyond a single screen.
Launch the AttackBox if you haven’t done so already. After you make sure that you
have terminated the VM from Task 4, start the VM for this task. Wait for it to load
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completely, then open the terminal on the AttackBox and use Nmap with nmap -sS -
F --reason MACHINE_IP to scan the VM. What is the reason provided for the stated
port(s) being open?
SYN-ACK
Task 9 Summary
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Ensure you have taken note of all the Nmap options explained in this room. Please
join the Nmap Post Port Scans room, the last room in this Nmap series.
No answer needed
thankyou
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Cindy (Shunxian) Ou
12 1
Timlssnss
50
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