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I will be using NMAP, Download here if you havent already: https://nmap.org/download

The goal of this project was to understand the difference between Footprinting & Fingerprinting with the knowledge on implementing them accordingly.

Footprinting is scanning the entire network topology while Fingerprinting is scanning a specific target to gain further service type info etc...

NOTE: Some options need superuser/admin priv.

WARNING: DO NOT USE IN LIVE ENVIRONMENTS WITHOUT EXPLICIT AUTHORITY. USER IS RESPONSIBLE FOR OWN ACTIONS. NMAP IS EASILY DETECTED. UNLAWFUL USE MAY RESULT UP TO FELONY CHARGES.

You can always pull up the manual by using 'man nmap' or 'nmap -h' depending on OS.

Once installed you can start scanning specific targets or do a whole network scan. -Targeted sweep: nmap 10.0.7.10
-Network sweep: nmap 10.0.7.1-254

TO DO A FOOTPRINT: Since this is used to obtain info about a network topology, you will be using the network sweep version. Use any additional options like -sV -Pn and even any other scripting tools. Ex: nmap -sV -O 10.0.7.1-254

TO DO A FINGERPRINT: Used along side enumeration, you are gathering specific information on a specific target. You can use the same options, however I do recommend for testing security try to use avoidance techniques to ensure blue team strength. Ex: nmap -Pn -sV -vvvv 10.0.7.6

ADDITIONAL OPTIONS I FOUND TO BE USEFUL: -Port Scanning techniques-

  • -sS (TCP SYN scan) SYN scan is the default and most popular scan option for good reasons. It can be performed quickly, scanning thousands of ports per second on a fast network not hampered by restrictive firewalls. It is also relatively unobtrusive and stealthy since it never completes TCP connections. SYN scan works against any compliant TCP stack rather than depending on idiosyncrasies of specific platforms as Nmap's FIN/NULL/Xmas, Maimon and idle scans do. It also allows clear, reliable differentiation between the open, closed, and filtered states.

This technique is often referred to as half-open scanning, because you don't open a full TCP connection. You send a SYN packet, as if you are going to open a real connection and then wait for a response. A SYN/ACK indicates the port is listening (open), while a RST (reset) is indicative of a non-listener. If no response is received after several retransmissions, the port is marked as filtered. The port is also marked filtered if an ICMP unreachable error (type 3, code 0, 1, 2, 3, 9, 10, or 13) is received. The port is also considered open if a SYN packet (without the ACK flag) is received in response. This can be due to an extremely rare TCP feature known as a simultaneous open or split handshake connection (see https://nmap.org/misc/split-handshake.pdf).

  • -sT (TCP connect scan) TCP connect scan is the default TCP scan type when SYN scan is not an option. This is the case when a user does not have raw packet privileges. Instead of writing raw packets as most other scan types do, Nmap asks the underlying operating system to establish a connection with the target machine and port by issuing the connect system call. This is the same high-level system call that web browsers, P2P clients, and most other network-enabled applications use to establish a connection. It is part of a programming interface known as the Berkeley Sockets API. Rather than read raw packet responses off the wire, Nmap uses this API to obtain status information on each connection attempt.

When SYN scan is available, it is usually a better choice. Nmap has less control over the high level connect call than with raw packets, making it less efficient. The system call completes connections to open target ports rather than performing the half-open reset that SYN scan does. Not only does this take longer and require more packets to obtain the same information, but target machines are more likely to log the connection. A decent IDS will catch either, but most machines have no such alarm system. Many services on your average Unix system will add a note to syslog, and sometimes a cryptic error message, when Nmap connects and then closes the connection without sending data. Truly pathetic services crash when this happens, though that is uncommon. An administrator who sees a bunch of connection attempts in her logs from a single system should know that she has been connect scanned.

  • -sU (UDP scans) While most popular services on the Internet run over the TCP protocol, UDP services are widely deployed. DNS, SNMP, and DHCP (registered ports 53, 161/162, and 67/68) are three of the most common. Because UDP scanning is generally slower and more difficult than TCP, some security auditors ignore these ports. This is a mistake, as exploitable UDP services are quite common and attackers certainly don't ignore the whole protocol. Fortunately, Nmap can help inventory UDP ports.

UDP scan is activated with the -sU option. It can be combined with a TCP scan type such as SYN scan (-sS) to check both protocols during the same run.

UDP scan works by sending a UDP packet to every targeted port. For some common ports such as 53 and 161, a protocol-specific payload is sent to increase response rate, but for most ports the packet is empty unless the --data, --data-string, or --data-length options are specified. If an ICMP port unreachable error (type 3, code 3) is returned, the port is closed. Other ICMP unreachable errors (type 3, codes 0, 1, 2, 9, 10, or 13) mark the port as filtered. Occasionally, a service will respond with a UDP packet, proving that it is open. If no response is received after retransmissions, the port is classified as open|filtered. This means that the port could be open, or perhaps packet filters are blocking the communication. Version detection (-sV) can be used to help differentiate the truly open ports from the filtered ones.

A big challenge with UDP scanning is doing it quickly. Open and filtered ports rarely send any response, leaving Nmap to time out and then conduct retransmissions just in case the probe or response were lost. Closed ports are often an even bigger problem. They usually send back an ICMP port unreachable error. But unlike the RST packets sent by closed TCP ports in response to a SYN or connect scan, many hosts rate limit ICMP port unreachable messages by default. Linux and Solaris are particularly strict about this. For example, the Linux 2.4.20 kernel limits destination unreachable messages to one per second (in net/ipv4/icmp.c).

Nmap detects rate limiting and slows down accordingly to avoid flooding the network with useless packets that the target machine will drop. Unfortunately, a Linux-style limit of one packet per second makes a 65,536-port scan take more than 18 hours. Ideas for speeding your UDP scans up include scanning more hosts in parallel, doing a quick scan of just the popular ports first, scanning from behind the firewall, and using --host-timeout to skip slow hosts.

  • -sY (SCTP INIT scan) SCTP is a relatively new alternative to the TCP and UDP protocols, combining most characteristics of TCP and UDP, and also adding new features like multi-homing and multi-streaming. It is mostly being used for SS7/SIGTRAN related services but has the potential to be used for other applications as well. SCTP INIT scan is the SCTP equivalent of a TCP SYN scan. It can be performed quickly, scanning thousands of ports per second on a fast network not hampered by restrictive firewalls. Like SYN scan, INIT scan is relatively unobtrusive and stealthy, since it never completes SCTP associations. It also allows clear, reliable differentiation between the open, closed, and filtered states.

This technique is often referred to as half-open scanning, because you don't open a full SCTP association. You send an INIT chunk, as if you are going to open a real association and then wait for a response. An INIT-ACK chunk indicates the port is listening (open), while an ABORT chunk is indicative of a non-listener. If no response is received after several retransmissions, the port is marked as filtered. The port is also marked filtered if an ICMP unreachable error (type 3, code 0, 1, 2, 3, 9, 10, or 13) is received.

-sN; -sF; -sX (TCP NULL, FIN, and Xmas scans) These three scan types (even more are possible with the --scanflags option described in the next section) exploit a subtle loophole in the TCP RFC to differentiate between open and closed ports. Page 65 of RFC 793 says that “if the [destination] port state is CLOSED .... an incoming segment not containing a RST causes a RST to be sent in response.” Then the next page discusses packets sent to open ports without the SYN, RST, or ACK bits set, stating that: “you are unlikely to get here, but if you do, drop the segment, and return.”

When scanning systems compliant with this RFC text, any packet not containing SYN, RST, or ACK bits will result in a returned RST if the port is closed and no response at all if the port is open. As long as none of those three bits are included, any combination of the other three (FIN, PSH, and URG) are OK. Nmap exploits this with three scan types:

Null scan (-sN) Does not set any bits (TCP flag header is 0)

FIN scan (-sF) Sets just the TCP FIN bit.

Xmas scan (-sX) Sets the FIN, PSH, and URG flags, lighting the packet up like a Christmas tree.

These three scan types are exactly the same in behavior except for the TCP flags set in probe packets. If a RST packet is received, the port is considered closed, while no response means it is open|filtered. The port is marked filtered if an ICMP unreachable error (type 3, code 0, 1, 2, 3, 9, 10, or 13) is received.

The key advantage to these scan types is that they can sneak through certain non-stateful firewalls and packet filtering routers. Another advantage is that these scan types are a little more stealthy than even a SYN scan. Don't count on this though—most modern IDS products can be configured to detect them. The big downside is that not all systems follow RFC 793 to the letter. A number of systems send RST responses to the probes regardless of whether the port is open or not. This causes all of the ports to be labeled closed. Major operating systems that do this are Microsoft Windows, many Cisco devices, BSDI, and IBM OS/400. This scan does work against most Unix-based systems though. Another downside of these scans is that they can't distinguish open ports from certain filtered ones, leaving you with the response open|filtered.

  • -sA (TCP ACK scan) This scan is different than the others discussed so far in that it never determines open (or even open|filtered) ports. It is used to map out firewall rulesets, determining whether they are stateful or not and which ports are filtered.

The ACK scan probe packet has only the ACK flag set (unless you use --scanflags). When scanning unfiltered systems, open and closed ports will both return a RST packet. Nmap then labels them as unfiltered, meaning that they are reachable by the ACK packet, but whether they are open or closed is undetermined. Ports that don't respond, or send certain ICMP error messages back (type 3, code 0, 1, 2, 3, 9, 10, or 13), are labeled filtered.

  • -sW (TCP Window scan) Window scan is exactly the same as ACK scan except that it exploits an implementation detail of certain systems to differentiate open ports from closed ones, rather than always printing unfiltered when a RST is returned. It does this by examining the TCP Window field of the RST packets returned. On some systems, open ports use a positive window size (even for RST packets) while closed ones have a zero window. So instead of always listing a port as unfiltered when it receives a RST back, Window scan lists the port as open or closed if the TCP Window value in that reset is positive or zero, respectively.

This scan relies on an implementation detail of a minority of systems out on the Internet, so you can't always trust it. Systems that don't support it will usually return all ports closed. Of course, it is possible that the machine really has no open ports. If most scanned ports are closed but a few common port numbers (such as 22, 25, 53) are filtered, the system is most likely susceptible. Occasionally, systems will even show the exact opposite behavior. If your scan shows 1,000 open ports and three closed or filtered ports, then those three may very well be the truly open ones.

  • -sM (TCP Maimon scan) The Maimon scan is named after its discoverer, Uriel Maimon. He described the technique in Phrack Magazine issue #49 (November 1996). Nmap, which included this technique, was released two issues later. This technique is exactly the same as NULL, FIN, and Xmas scans, except that the probe is FIN/ACK. According to RFC 793 (TCP), a RST packet should be generated in response to such a probe whether the port is open or closed. However, Uriel noticed that many BSD-derived systems simply drop the packet if the port is open.

--scanflags (Custom TCP scan) Truly advanced Nmap users need not limit themselves to the canned scan types offered. The --scanflags option allows you to design your own scan by specifying arbitrary TCP flags. Let your creative juices flow, while evading intrusion detection systems whose vendors simply paged through the Nmap man page adding specific rules!

The --scanflags argument can be a numerical flag value such as 9 (PSH and FIN), but using symbolic names is easier. Just mash together any combination of URG, ACK, PSH, RST, SYN, and FIN. For example, --scanflags URGACKPSHRSTSYNFIN sets everything, though it's not very useful for scanning. The order these are specified in is irrelevant.

In addition to specifying the desired flags, you can specify a TCP scan type (such as -sA or -sF). That base type tells Nmap how to interpret responses. For example, a SYN scan considers no-response to indicate a filtered port, while a FIN scan treats the same as open|filtered. Nmap will behave the same way it does for the base scan type, except that it will use the TCP flags you specify instead. If you don't specify a base type, SYN scan is used.

  • -sZ (SCTP COOKIE ECHO scan) SCTP COOKIE ECHO scan is a more advanced SCTP scan. It takes advantage of the fact that SCTP implementations should silently drop packets containing COOKIE ECHO chunks on open ports, but send an ABORT if the port is closed. The advantage of this scan type is that it is not as obvious a port scan than an INIT scan. Also, there may be non-stateful firewall rulesets blocking INIT chunks, but not COOKIE ECHO chunks. Don't be fooled into thinking that this will make a port scan invisible; a good IDS will be able to detect SCTP COOKIE ECHO scans too. The downside is that SCTP COOKIE ECHO scans cannot differentiate between open and filtered ports, leaving you with the state open|filtered in both cases.

  • -sI [:] (idle scan) This advanced scan method allows for a truly blind TCP port scan of the target (meaning no packets are sent to the target from your real IP address). Instead, a unique side-channel attack exploits predictable IP fragmentation ID sequence generation on the zombie host to glean information about the open ports on the target. IDS systems will display the scan as coming from the zombie machine you specify (which must be up and meet certain criteria). Full details of this fascinating scan type are in the section called “TCP Idle Scan (-sI)”.

Besides being extraordinarily stealthy (due to its blind nature), this scan type permits mapping out IP-based trust relationships between machines. The port listing shows open ports from the perspective of the zombie host. So you can try scanning a target using various zombies that you think might be trusted (via router/packet filter rules).

You can add a colon followed by a port number to the zombie host if you wish to probe a particular port on the zombie for IP ID changes. Otherwise Nmap will use the port it uses by default for TCP pings (80).

  • -sO (IP protocol scan) IP protocol scan allows you to determine which IP protocols (TCP, ICMP, IGMP, etc.) are supported by target machines. This isn't technically a port scan, since it cycles through IP protocol numbers rather than TCP or UDP port numbers. Yet it still uses the -p option to select scanned protocol numbers, reports its results within the normal port table format, and even uses the same underlying scan engine as the true port scanning methods. So it is close enough to a port scan that it belongs here.

Besides being useful in its own right, protocol scan demonstrates the power of open-source software. While the fundamental idea is pretty simple, I had not thought to add it nor received any requests for such functionality. Then in the summer of 2000, Gerhard Rieger conceived the idea, wrote an excellent patch implementing it, and sent it to the announce mailing list (then called nmap-hackers). I incorporated that patch into the Nmap tree and released a new version the next day. Few pieces of commercial software have users enthusiastic enough to design and contribute their own improvements!

Protocol scan works in a similar fashion to UDP scan. Instead of iterating through the port number field of a UDP packet, it sends IP packet headers and iterates through the eight-bit IP protocol field. The headers are usually empty, containing no data and not even the proper header for the claimed protocol. The exceptions are TCP, UDP, ICMP, SCTP, and IGMP. A proper protocol header for those is included since some systems won't send them otherwise and because Nmap already has functions to create them. Instead of watching for ICMP port unreachable messages, protocol scan is on the lookout for ICMP protocol unreachable messages. If Nmap receives any response in any protocol from the target host, Nmap marks that protocol as open. An ICMP protocol unreachable error (type 3, code 2) causes the protocol to be marked as closed while port unreachable (type 3, code 3) marks the protocol open. Other ICMP unreachable errors (type 3, code 0, 1, 9, 10, or 13) cause the protocol to be marked filtered (though they prove that ICMP is open at the same time). If no response is received after retransmissions, the protocol is marked open|filtered

  • -b (FTP bounce scan) An interesting feature of the FTP protocol (RFC 959) is support for so-called proxy FTP connections. This allows a user to connect to one FTP server, then ask that files be sent to a third-party server. Such a feature is ripe for abuse on many levels, so most servers have ceased supporting it. One of the abuses this feature allows is causing the FTP server to port scan other hosts. Simply ask the FTP server to send a file to each interesting port of a target host in turn. The error message will describe whether the port is open or not. This is a good way to bypass firewalls because organizational FTP servers are often placed where they have more access to other internal hosts than any old Internet host would. Nmap supports FTP bounce scan with the -b option. It takes an argument of the form :@:. is the name or IP address of a vulnerable FTP server. As with a normal URL, you may omit :, in which case anonymous login credentials (user: anonymous password:-wwwuser@) are used. The port number (and preceding colon) may be omitted as well, in which case the default FTP port (21) on is used.

This vulnerability was widespread in 1997 when Nmap was released, but has largely been fixed. Vulnerable servers are still around, so it is worth trying when all else fails. If bypassing a firewall is your goal, scan the target network for port 21 (or even for any FTP services if you scan all ports with version detection) and use the ftp-bounce NSE script. Nmap will tell you whether the host is vulnerable or not. If you are just trying to cover your tracks, you don't need to (and, in fact, shouldn't) limit yourself to hosts on the target network. Before you go scanning random Internet addresses for vulnerable FTP servers, consider that sysadmins may not appreciate you abusing their servers in this way.

-Service Detection-

  • -sV (Version detection) Enables version detection, as discussed above. Alternatively, you can use -A, which enables version detection among other things.

  • -sR is an alias for -sV. Prior to March 2011, it was used to active the RPC grinder separately from version detection, but now these options are always combined.

--allports (Don't exclude any ports from version detection) By default, Nmap version detection skips TCP port 9100 because some printers simply print anything sent to that port, leading to dozens of pages of HTTP GET requests, binary SSL session requests, etc. This behavior can be changed by modifying or removing the Exclude directive in nmap-service-probes, or you can specify --allports to scan all ports regardless of any Exclude directive.

--version-intensity (Set version scan intensity) When performing a version scan (-sV), Nmap sends a series of probes, each of which is assigned a rarity value between one and nine. The lower-numbered probes are effective against a wide variety of common services, while the higher-numbered ones are rarely useful. The intensity level specifies which probes should be applied. The higher the number, the more likely it is the service will be correctly identified. However, high intensity scans take longer. The intensity must be between 0 and 9. The default is 7. When a probe is registered to the target port via the nmap-service-probes ports directive, that probe is tried regardless of intensity level. This ensures that the DNS probes will always be attempted against any open port 53, the SSL probe will be done against 443, etc.

--version-light (Enable light mode) This is a convenience alias for --version-intensity 2. This light mode makes version scanning much faster, but it is slightly less likely to identify services.

--version-all (Try every single probe) An alias for --version-intensity 9, ensuring that every single probe is attempted against each port.

--version-trace (Trace version scan activity) This causes Nmap to print out extensive debugging info about what version scanning is doing. It is a subset of what you get with --packet-trace.

-OS detection-

  • -O (Enable OS detection) Enables OS detection, as discussed above. Alternatively, you can use -A to enable OS detection along with other things.

--osscan-limit (Limit OS detection to promising targets) OS detection is far more effective if at least one open and one closed TCP port are found. Set this option and Nmap will not even try OS detection against hosts that do not meet this criteria. This can save substantial time, particularly on -Pn scans against many hosts. It only matters when OS detection is requested with -O or -A.

--osscan-guess; --fuzzy (Guess OS detection results) When Nmap is unable to detect a perfect OS match, it sometimes offers up near-matches as possibilities. The match has to be very close for Nmap to do this by default. Either of these (equivalent) options make Nmap guess more aggressively. Nmap will still tell you when an imperfect match is printed and display its confidence level (percentage) for each guess.

--max-os-tries (Set the maximum number of OS detection tries against a target) When Nmap performs OS detection against a target and fails to find a perfect match, it usually repeats the attempt. By default, Nmap tries five times if conditions are favorable for OS fingerprint submission, and twice when conditions aren't so good. Specifying a lower --max-os-tries value (such as 1) speeds Nmap up, though you miss out on retries which could potentially identify the OS. Alternatively, a high value may be set to allow even more retries when conditions are favorable. This is rarely done, except to generate better fingerprints for submission and integration into the Nmap OS database.

-Host discovery-

  • -sL (List Scan) The list scan is a degenerate form of host discovery that simply lists each host of the network(s) specified, without sending any packets to the target hosts. By default, Nmap still does reverse-DNS resolution on the hosts to learn their names. It is often surprising how much useful information simple hostnames give out. For example, fw.chi is the name of one company's Chicago firewall. Nmap also reports the total number of IP addresses at the end. The list scan is a good sanity check to ensure that you have proper IP addresses for your targets. If the hosts sport domain names you do not recognize, it is worth investigating further to prevent scanning the wrong company's network.

Since the idea is to simply print a list of target hosts, options for higher level functionality such as port scanning, OS detection, or host discovery cannot be combined with this. If you wish to disable host discovery while still performing such higher level functionality, read up on the -Pn (skip host discovery) option.

  • -sn (No port scan) This option tells Nmap not to do a port scan after host discovery, and only print out the available hosts that responded to the host discovery probes. This is often known as a “ping scan”, but you can also request that traceroute and NSE host scripts be run. This is by default one step more intrusive than the list scan, and can often be used for the same purposes. It allows light reconnaissance of a target network without attracting much attention. Knowing how many hosts are up is more valuable to attackers than the list provided by list scan of every single IP and host name.

Systems administrators often find this option valuable as well. It can easily be used to count available machines on a network or monitor server availability. This is often called a ping sweep, and is more reliable than pinging the broadcast address because many hosts do not reply to broadcast queries.

The default host discovery done with -sn consists of an ICMP echo request, TCP SYN to port 443, TCP ACK to port 80, and an ICMP timestamp request by default. When executed by an unprivileged user, only SYN packets are sent (using a connect call) to ports 80 and 443 on the target. When a privileged user tries to scan targets on a local ethernet network, ARP requests are used unless --send-ip was specified. The -sn option can be combined with any of the discovery probe types (the -P* options) for greater flexibility. If any of those probe type and port number options are used, the default probes are overridden. When strict firewalls are in place between the source host running Nmap and the target network, using those advanced techniques is recommended. Otherwise hosts could be missed when the firewall drops probes or their responses.

In previous releases of Nmap, -sn was known as -sP.

  • -Pn (No ping) This option skips the host discovery stage altogether. Normally, Nmap uses this stage to determine active machines for heavier scanning and to gauge the speed of the network. By default, Nmap only performs heavy probing such as port scans, version detection, or OS detection against hosts that are found to be up. Disabling host discovery with -Pn causes Nmap to attempt the requested scanning functions against every target IP address specified. So if a /16 sized network is specified on the command line, all 65,536 IP addresses are scanned. Proper host discovery is skipped as with the list scan, but instead of stopping and printing the target list, Nmap continues to perform requested functions as if each target IP is active. Default timing parameters are used, which may result in slower scans. To skip host discovery and port scan, while still allowing NSE to run, use the two options -Pn -sn together.

For machines on a local ethernet network, ARP scanning will still be performed (unless --disable-arp-ping or --send-ip is specified) because Nmap needs MAC addresses to further scan target hosts. In previous versions of Nmap, -Pn was -P0 and -PN.

  • -PS (TCP SYN Ping) This option sends an empty TCP packet with the SYN flag set. The default destination port is 80 (configurable at compile time by changing DEFAULT_TCP_PROBE_PORT_SPEC in nmap.h). Alternate ports can be specified as a parameter. The syntax is the same as for the -p except that port type specifiers like T: are not allowed. Examples are -PS22 and -PS22-25,80,113,1050,35000. Note that there can be no space between -PS and the port list. If multiple probes are specified they will be sent in parallel.

The SYN flag suggests to the remote system that you are attempting to establish a connection. Normally the destination port will be closed, and a RST (reset) packet sent back. If the port happens to be open, the target will take the second step of a TCP three-way-handshake by responding with a SYN/ACK TCP packet. The machine running Nmap then tears down the nascent connection by responding with a RST rather than sending an ACK packet which would complete the three-way-handshake and establish a full connection. The RST packet is sent by the kernel of the machine running Nmap in response to the unexpected SYN/ACK, not by Nmap itself.

Nmap does not care whether the port is open or closed. Either the RST or SYN/ACK response discussed previously tell Nmap that the host is available and responsive.

On Unix boxes, only the privileged user root is generally able to send and receive raw TCP packets. For unprivileged users, a workaround is automatically employed whereby the connect system call is initiated against each target port. This has the effect of sending a SYN packet to the target host, in an attempt to establish a connection. If connect returns with a quick success or an ECONNREFUSED failure, the underlying TCP stack must have received a SYN/ACK or RST and the host is marked available. If the connection attempt is left hanging until a timeout is reached, the host is marked as down.

  • -PA (TCP ACK Ping) The TCP ACK ping is quite similar to the just-discussed SYN ping. The difference, as you could likely guess, is that the TCP ACK flag is set instead of the SYN flag. Such an ACK packet purports to be acknowledging data over an established TCP connection, but no such connection exists. So remote hosts should always respond with a RST packet, disclosing their existence in the process.

The -PA option uses the same default port as the SYN probe (80) and can also take a list of destination ports in the same format. If an unprivileged user tries this, the connect workaround discussed previously is used. This workaround is imperfect because connect is actually sending a SYN packet rather than an ACK.

The reason for offering both SYN and ACK ping probes is to maximize the chances of bypassing firewalls. Many administrators configure routers and other simple firewalls to block incoming SYN packets except for those destined for public services like the company web site or mail server. This prevents other incoming connections to the organization, while allowing users to make unobstructed outgoing connections to the Internet. This non-stateful approach takes up few resources on the firewall/router and is widely supported by hardware and software filters. The Linux Netfilter/iptables firewall software offers the --syn convenience option to implement this stateless approach. When stateless firewall rules such as this are in place, SYN ping probes (-PS) are likely to be blocked when sent to closed target ports. In such cases, the ACK probe shines as it cuts right through these rules.

Another common type of firewall uses stateful rules that drop unexpected packets. This feature was initially found mostly on high-end firewalls, though it has become much more common over the years. The Linux Netfilter/iptables system supports this through the --state option, which categorizes packets based on connection state. A SYN probe is more likely to work against such a system, as unexpected ACK packets are generally recognized as bogus and dropped. A solution to this quandary is to send both SYN and ACK probes by specifying -PS and -PA.

  • -PU (UDP Ping) Another host discovery option is the UDP ping, which sends a UDP packet to the given ports. For most ports, the packet will be empty, though some use a protocol-specific payload that is more likely to elicit a response. The payloads are the same probes used in service and version detection and are defined in the nmap-service-probes file. Packet content can also be affected with the --data, --data-string, and --data-length options.

The port list takes the same format as with the previously discussed -PS and -PA options. If no ports are specified, the default is 40125. This default can be configured at compile-time by changing DEFAULT_UDP_PROBE_PORT_SPEC in nmap.h. A highly uncommon port is used by default because sending to open ports is often undesirable for this particular scan type.

Upon hitting a closed port on the target machine, the UDP probe should elicit an ICMP port unreachable packet in return. This signifies to Nmap that the machine is up and available. Many other types of ICMP errors, such as host/network unreachables or TTL exceeded are indicative of a down or unreachable host. A lack of response is also interpreted this way. If an open port is reached, most services simply ignore the empty packet and fail to return any response. This is why the default probe port is 40125, which is highly unlikely to be in use. A few services, such as the Character Generator (chargen) protocol, will respond to an empty UDP packet, and thus disclose to Nmap that the machine is available.

The primary advantage of this scan type is that it bypasses firewalls and filters that only screen TCP. For example, I once owned a Linksys BEFW11S4 wireless broadband router. The external interface of this device filtered all TCP ports by default, but UDP probes would still elicit port unreachable messages and thus give away the device.

  • -PY (SCTP INIT Ping) This option sends an SCTP packet containing a minimal INIT chunk. The default destination port is 80 (configurable at compile time by changing DEFAULT_SCTP_PROBE_PORT_SPEC in nmap.h). Alternate ports can be specified as a parameter. The syntax is the same as for the -p except that port type specifiers like S: are not allowed. Examples are -PY22 and -PY22,80,179,5060. Note that there can be no space between -PY and the port list. If multiple probes are specified they will be sent in parallel.

The INIT chunk suggests to the remote system that you are attempting to establish an association. Normally the destination port will be closed, and an ABORT chunk will be sent back. If the port happens to be open, the target will take the second step of an SCTP four-way-handshake by responding with an INIT-ACK chunk. If the machine running Nmap has a functional SCTP stack, then it tears down the nascent association by responding with an ABORT chunk rather than sending a COOKIE-ECHO chunk which would be the next step in the four-way-handshake. The ABORT packet is sent by the kernel of the machine running Nmap in response to the unexpected INIT-ACK, not by Nmap itself.

Nmap does not care whether the port is open or closed. Either the ABORT or INIT-ACK response discussed previously tell Nmap that the host is available and responsive.

On Unix boxes, only the privileged user root is generally able to send and receive raw SCTP packets. Using SCTP INIT Pings is currently not possible for unprivileged users.

  • PE; -PP; -PM (ICMP Ping Types) In addition to the unusual TCP, UDP and SCTP host discovery types discussed previously, Nmap can send the standard packets sent by the ubiquitous ping program. Nmap sends an ICMP type 8 (echo request) packet to the target IP addresses, expecting a type 0 (echo reply) in return from available hosts. Unfortunately for network explorers, many hosts and firewalls now block these packets, rather than responding as required by RFC 1122. For this reason, ICMP-only scans are rarely reliable enough against unknown targets over the Internet. But for system administrators monitoring an internal network, they can be a practical and efficient approach. Use the -PE option to enable this echo request behavior.

While echo request is the standard ICMP ping query, Nmap does not stop there. The ICMP standards (RFC 792 and RFC 950 ) also specify timestamp request, information request, and address mask request packets as codes 13, 15, and 17, respectively. While the ostensible purpose for these queries is to learn information such as address masks and current times, they can easily be used for host discovery. A system that replies is up and available. Nmap does not currently implement information request packets, as they are not widely supported. RFC 1122 insists that “a host SHOULD NOT implement these messages”. Timestamp and address mask queries can be sent with the -PP and -PM options, respectively. A timestamp reply (ICMP code 14) or address mask reply (code 18) discloses that the host is available. These two queries can be valuable when administrators specifically block echo request packets while forgetting that other ICMP queries can be used for the same purpose.

  • -PO (IP Protocol Ping) One of the newer host discovery options is the IP protocol ping, which sends IP packets with the specified protocol number set in their IP header. The protocol list takes the same format as do port lists in the previously discussed TCP, UDP and SCTP host discovery options. If no protocols are specified, the default is to send multiple IP packets for ICMP (protocol 1), IGMP (protocol 2), and IP-in-IP (protocol 4). The default protocols can be configured at compile-time by changing DEFAULT_PROTO_PROBE_PORT_SPEC in nmap.h. Note that for the ICMP, IGMP, TCP (protocol 6), UDP (protocol 17) and SCTP (protocol 132), the packets are sent with the proper protocol headers while other protocols are sent with no additional data beyond the IP header (unless any of --data, --data-string, or --data-length options are specified).

This host discovery method looks for either responses using the same protocol as a probe, or ICMP protocol unreachable messages which signify that the given protocol isn't supported on the destination host. Either type of response signifies that the target host is alive.

--disable-arp-ping (No ARP or ND Ping) Nmap normally does ARP or IPv6 Neighbor Discovery (ND) discovery of locally connected ethernet hosts, even if other host discovery options such as -Pn or -PE are used. To disable this implicit behavior, use the --disable-arp-ping option.

The default behavior is normally faster, but this option is useful on networks using proxy ARP, in which a router speculatively replies to all ARP requests, making every target appear to be up according to ARP scan.

--discovery-ignore-rst In some cases, firewalls may spoof TCP reset (RST) replies in response to probes to unoccupied or disallowed addresses. Since Nmap ordinarily considers RST replies to be proof that the target is up, this can lead to wasted time scanning targets that aren't there. Using the --discovery-ignore-rst will prevent Nmap from considering these replies during host discovery. You may need to select extra host discovery options to ensure you don't miss targets in this case.

--traceroute (Trace path to host) Traceroutes are performed post-scan using information from the scan results to determine the port and protocol most likely to reach the target. It works with all scan types except connect scans (-sT) and idle scans (-sI). All traces use Nmap's dynamic timing model and are performed in parallel.

Traceroute works by sending packets with a low TTL (time-to-live) in an attempt to elicit ICMP Time Exceeded messages from intermediate hops between the scanner and the target host. Standard traceroute implementations start with a TTL of 1 and increment the TTL until the destination host is reached. Nmap's traceroute starts with a high TTL and then decrements the TTL until it reaches zero. Doing it backwards lets Nmap employ clever caching algorithms to speed up traces over multiple hosts. On average Nmap sends 5–10 fewer packets per host, depending on network conditions. If a single subnet is being scanned (i.e. 192.168.0.0/24) Nmap may only have to send two packets to most hosts.

-Evasion-

  • -f (fragment packets); --mtu (using the specified MTU) The -f option causes the requested scan (including host discovery scans) to use tiny fragmented IP packets. The idea is to split up the TCP header over several packets to make it harder for packet filters, intrusion detection systems, and other annoyances to detect what you are doing. Be careful with this! Some programs have trouble handling these tiny packets. The old-school sniffer named Sniffit segmentation faulted immediately upon receiving the first fragment. Specify this option once, and Nmap splits the packets into eight bytes or less after the IP header. So a 20-byte TCP header would be split into three packets. Two with eight bytes of the TCP header, and one with the final four. Of course each fragment also has an IP header. Specify -f again to use 16 bytes per fragment (reducing the number of fragments). Or you can specify your own offset size with the --mtu option. Don't also specify -f if you use --mtu. The offset must be a multiple of eight. While fragmented packets won't get by packet filters and firewalls that queue all IP fragments, such as the CONFIG_IP_ALWAYS_DEFRAG option in the Linux kernel, some networks can't afford the performance hit this causes and thus leave it disabled. Others can't enable this because fragments may take different routes into their networks. Some source systems defragment outgoing packets in the kernel. Linux with the iptables connection tracking module is one such example. Do a scan while a sniffer such as Wireshark is running to ensure that sent packets are fragmented. If your host OS is causing problems, try the --send-eth option to bypass the IP layer and send raw ethernet frames.

Fragmentation is only supported for Nmap's raw packet features, which includes TCP and UDP port scans (except connect scan and FTP bounce scan) and OS detection. Features such as version detection and the Nmap Scripting Engine generally don't support fragmentation because they rely on your host's TCP stack to communicate with target services.

  • -D [,][,ME][,...] (Cloak a scan with decoys) Causes a decoy scan to be performed, which makes it appear to the remote host that the host(s) you specify as decoys are scanning the target network too. Thus their IDS might report 5–10 port scans from unique IP addresses, but they won't know which IP was scanning them and which were innocent decoys. While this can be defeated through router path tracing, response-dropping, and other active mechanisms, it is generally an effective technique for hiding your IP address.

Separate each decoy host with commas, and you can optionally use ME as one of the decoys to represent the position for your real IP address. If you put ME in the sixth position or later, some common port scan detectors (such as Solar Designer's excellent Scanlogd) are unlikely to show your IP address at all. If you don't use ME, Nmap will put you in a random position. You can also use RND to generate a random, non-reserved IP address, or RND: to generate addresses.

Note that the hosts you use as decoys should be up or you might accidentally SYN flood your targets. Also it will be pretty easy to determine which host is scanning if only one is actually up on the network. You might want to use IP addresses instead of names (so the decoy networks don't see you in their nameserver logs). Right now random IP address generation is only supported with IPv4

Decoys are used both in the initial host discovery scan (using ICMP, SYN, ACK, or whatever) and during the actual port scanning phase. Decoys are also used during remote OS detection (-O). Decoys do not work with version detection or TCP connect scan. When a scan delay is in effect, the delay is enforced between each batch of spoofed probes, not between each individual probe. Because decoys are sent as a batch all at once, they may temporarily violate congestion control limits.

It is worth noting that using too many decoys may slow your scan and potentially even make it less accurate. Also, some ISPs will filter out your spoofed packets, but many do not restrict spoofed IP packets at all.

  • -S <IP_Address> (Spoof source address) In some circumstances, Nmap may not be able to determine your source address (Nmap will tell you if this is the case). In this situation, use -S with the IP address of the interface you wish to send packets through.

Another possible use of this flag is to spoof the scan to make the targets think that someone else is scanning them. Imagine a company being repeatedly port scanned by a competitor! The -e option and -Pn are generally required for this sort of usage. Note that you usually won't receive reply packets back (they will be addressed to the IP you are spoofing), so Nmap won't produce useful reports.

  • -e (Use specified interface) Tells Nmap what interface to send and receive packets on. Nmap should be able to detect this automatically, but it will tell you if it cannot.

--source-port ; -g (Spoof source port number) One surprisingly common misconfiguration is to trust traffic based only on the source port number. It is easy to understand how this comes about. An administrator will set up a shiny new firewall, only to be flooded with complaints from ungrateful users whose applications stopped working. In particular, DNS may be broken because the UDP DNS replies from external servers can no longer enter the network. FTP is another common example. In active FTP transfers, the remote server tries to establish a connection back to the client to transfer the requested file.

Secure solutions to these problems exist, often in the form of application-level proxies or protocol-parsing firewall modules. Unfortunately there are also easier, insecure solutions. Noting that DNS replies come from port 53 and active FTP from port 20, many administrators have fallen into the trap of simply allowing incoming traffic from those ports. They often assume that no attacker would notice and exploit such firewall holes. In other cases, administrators consider this a short-term stop-gap measure until they can implement a more secure solution. Then they forget the security upgrade.

Overworked network administrators are not the only ones to fall into this trap. Numerous products have shipped with these insecure rules. Even Microsoft has been guilty. The IPsec filters that shipped with Windows 2000 and Windows XP contain an implicit rule that allows all TCP or UDP traffic from port 88 (Kerberos). In another well-known case, versions of the Zone Alarm personal firewall up to 2.1.25 allowed any incoming UDP packets with the source port 53 (DNS) or 67 (DHCP).

Nmap offers the -g and --source-port options (they are equivalent) to exploit these weaknesses. Simply provide a port number and Nmap will send packets from that port where possible. Most scanning operations that use raw sockets, including SYN and UDP scans, support the option completely. The option notably doesn't have an effect for any operations that use normal operating system sockets, including DNS requests, TCP connect scan, version detection, and script scanning. Setting the source port also doesn't work for OS detection, because Nmap must use different port numbers for certain OS detection tests to work properly.

--data (Append custom binary data to sent packets) This option lets you include binary data as payload in sent packets. may be specified in any of the following formats: 0xAABBCCDDEEFF<...>, AABBCCDDEEFF<...> or \xAA\xBB\xCC\xDD\xEE\xFF<...>. Examples of use are --data 0xdeadbeef and --data \xCA\xFE\x09. Note that if you specify a number like 0x00ff no byte-order conversion is performed. Make sure you specify the information in the byte order expected by the receiver.

--data-string (Append custom string to sent packets) This option lets you include a regular string as payload in sent packets. can contain any string. However, note that some characters may depend on your system's locale and the receiver may not see the same information. Also, make sure you enclose the string in double quotes and escape any special characters from the shell. Examples: --data-string "Scan conducted by Security Ops, extension 7192" or --data-string "Ph34r my l33t skills". Keep in mind that nobody is likely to actually see any comments left by this option unless they are carefully monitoring the network with a sniffer or custom IDS rules.

--data-length (Append random data to sent packets) Normally Nmap sends minimalist packets containing only a header. So its TCP packets are generally 40 bytes and ICMP echo requests are just 28. Some UDP ports and IP protocols get a custom payload by default. This option tells Nmap to append the given number of random bytes to most of the packets it sends, and not to use any protocol-specific payloads. (Use --data-length 0 for no random or protocol-specific payloads. OS detection (-O) packets are not affected because accuracy there requires probe consistency, but most pinging and portscan packets support this. It slows things down a little, but can make a scan slightly less conspicuous.

--ip-options <R|S [route]|L [route]|T|U ... >; --ip-options (Send packets with specified ip options) The IP protocol offers several options which may be placed in packet headers. Unlike the ubiquitous TCP options, IP options are rarely seen due to practicality and security concerns. In fact, many Internet routers block the most dangerous options such as source routing. Yet options can still be useful in some cases for determining and manipulating the network route to target machines. For example, you may be able to use the record route option to determine a path to a target even when more traditional traceroute-style approaches fail. Or if your packets are being dropped by a certain firewall, you may be able to specify a different route with the strict or loose source routing options.

The most powerful way to specify IP options is to simply pass in values as the argument to --ip-options. Precede each hex number with \x then the two digits. You may repeat certain characters by following them with an asterisk and then the number of times you wish them to repeat. For example, \x01\x07\x04\x00*36\x01 is a hex string containing 36 NUL bytes.

Nmap also offers a shortcut mechanism for specifying options. Simply pass the letter R, T, or U to request record-route, record-timestamp, or both options together, respectively. Loose or strict source routing may be specified with an L or S followed by a space and then a space-separated list of IP addresses.

If you wish to see the options in packets sent and received, specify --packet-trace. For more information and examples of using IP options with Nmap, see https://seclists.org/nmap-dev/2006/q3/52.

--ttl (Set IP time-to-live field) Sets the IPv4 time-to-live field in sent packets to the given value.

--randomize-hosts (Randomize target host order) Tells Nmap to shuffle each group of up to 16384 hosts before it scans them. This can make the scans less obvious to various network monitoring systems, especially when you combine it with slow timing options. If you want to randomize over larger group sizes, increase PING_GROUP_SZ in nmap.h and recompile. An alternative solution is to generate the target IP list with a list scan (-sL -n -oN ), randomize it with a Perl script, then provide the whole list to Nmap with -iL.

--spoof-mac <MAC address, prefix, or vendor name> (Spoof MAC address) Asks Nmap to use the given MAC address for all of the raw ethernet frames it sends. This option implies --send-eth to ensure that Nmap actually sends ethernet-level packets. The MAC given can take several formats. If it is simply the number 0, Nmap chooses a completely random MAC address for the session. If the given string is an even number of hex digits (with the pairs optionally separated by a colon), Nmap will use those as the MAC. If fewer than 12 hex digits are provided, Nmap fills in the remainder of the six bytes with random values. If the argument isn't a zero or hex string, Nmap looks through nmap-mac-prefixes to find a vendor name containing the given string (it is case insensitive). If a match is found, Nmap uses the vendor's OUI (three-byte prefix) and fills out the remaining three bytes randomly. Valid --spoof-mac argument examples are Apple, 0, 01:02:03:04:05:06, deadbeefcafe, 0020F2, and Cisco. This option only affects raw packet scans such as SYN scan or OS detection, not connection-oriented features such as version detection or the Nmap Scripting Engine.

--proxies (Relay TCP connections through a chain of proxies) Asks Nmap to establish TCP connections with a final target through supplied chain of one or more HTTP or SOCKS4 proxies. Proxies can help hide the true source of a scan or evade certain firewall restrictions, but they can hamper scan performance by increasing latency. Users may need to adjust Nmap timeouts and other scan parameters accordingly. In particular, a lower --max-parallelism may help because some proxies refuse to handle as many concurrent connections as Nmap opens by default.

This option takes a list of proxies as argument, expressed as URLs in the format proto://host:port. Use commas to separate node URLs in a chain. No authentication is supported yet. Valid protocols are HTTP and SOCKS4.

Warning: this feature is still under development and has limitations. It is implemented within the nsock library and thus has no effect on the ping, port scanning and OS discovery phases of a scan. Only NSE and version scan benefit from this option so far—other features may disclose your true address. SSL connections are not yet supported, nor is proxy-side DNS resolution (hostnames are always resolved by Nmap).

--badsum (Send packets with bogus TCP/UDP checksums) Asks Nmap to use an invalid TCP, UDP or SCTP checksum for packets sent to target hosts. Since virtually all host IP stacks properly drop these packets, any responses received are likely coming from a firewall or IDS that didn't bother to verify the checksum. For more details on this technique, see https://nmap.org/p60-12.html

--adler32 (Use deprecated Adler32 instead of CRC32C for SCTP checksums) Asks Nmap to use the deprecated Adler32 algorithm for calculating the SCTP checksum. If --adler32 is not given, CRC-32C (Castagnoli) is used. RFC 2960 originally defined Adler32 as checksum algorithm for SCTP; RFC 4960 later redefined the SCTP checksums to use CRC-32C. Current SCTP implementations should be using CRC-32C, but in order to elicit responses from old, legacy SCTP implementations, it may be preferable to use Adler32.

-Searching for NSE scripts with 'ls | grep ftp' I found to be helpful. (cd into proper directory before grep command, for kali thats '/usr/share/nmap/scripts')

Said additional info can be found here: https://nmap.org/book/man.html