Scan our target host for open TCP ports.

There are actually a few TCP scans that nmap knows how to do. The best one to usually start off with is a SYN scan, also known as a “half-open scan” because it never actually negotiates a full TCP connection. This is often used by attackers because it fails to register on some intrusion detection systems because it never completes a full handshake.

Use tcpdump to capture the traffic generated by the test. This will be used to analyze the packets sent and received in more depth later on if we need to. Let's create a directory within ~/scan_results so that we can keep the files related to our SYN scan together:

mkdir ~/scan_results/syn_scan

We can start a tcpdump capture and write the results to a file in our ~/scan_results/syn_scan directory with the following command:

sudo tcpdump host target_ip_addr -w ~/scan_results/syn_scan/packets

By default, tcpdump will run in the foreground. In order to run our nmap scan in the same window, we'll need to pause the tcpdump process and then restart it in the background.

We can pause the running process by hitting CTRL-Z:

CTRL-Z

This will pause the running process:

Output

^Z
[1]+  Stopped                 sudo tcpdump host target_ip_addr -w ~/scan_results/syn_scan/packets

NOTE: You can restart the job in the background by typing bg:

bg

You should see a similar line of output, this time without the “Stopped” label and with an ampersand at the end to indicate that the process will be run in the background:

Output

[1]+ sudo tcpdump host target_ip_addr -w ~/scan_results/syn_scan/packets &

The command is now running in the background, watching for any packets going between our audit and target machines. We can now run our SYN scan.

With tcpdump recording our traffic to the target machine, we are ready to run nmap. We will use the following flags to get nmap to perform the actions we require:

• -sS: This starts a SYN scan. This is technically the default scan that nmap will perform if no scan type is given, but we will include it here to be explicit.
• -Pn: This tells nmap to skip the host discovery step, which would abort the test early if the host doesn't respond to a ping. Since we know that the target is online, we can skip this.
• -p-: By default, SYN scans will only try the 1000 most commonly used ports. This tells nmap to check every available port.
• -T4: This sets a timing profile for nmap, telling it to speed up the test at the risk of slightly less accurate results. 0 is the slowest and 5 is the fastest. Since we're scanning every port, we can use this as our baseline and re-check any ports later that might have been reported incorrectly.
• -vv: This increases the verbosity of the output.
• –reason: This tells nmap to provide the reason that a port's state was reported a certain way.
• -oN: This writes the results to a file that we can use for later analysis.

NOTE: One thing to keep in mind is that in order to check IPv6, you will need to add the -6 flag to your commands. Add this flag if your firewall accepts IPv6 traffic.

Together, the command will look something like this:

sudo nmap -sS -Pn -p- -T4 -vv --reason -oN ~/scan_results/syn_scan/nmap.results target_ip_addr

Even with the timing template set at 4, the scan will likely take quite some time as it runs through 65,535 ports. (The test may run for an hour or more). You will see results begin to print that look something like this:

Output

Starting Nmap 6.49BETA4 ( https://nmap.org ) at 2015-08-26 16:54 EDT
Initiating Parallel DNS resolution of 1 host. at 16:54
Completed Parallel DNS resolution of 1 host. at 16:54, 0.12s elapsed
Initiating SYN Stealth Scan at 16:54
Scanning 198.51.100.15 [65535 ports]
Discovered open port 22/tcp on 198.51.100.15
Discovered open port 80/tcp on 198.51.100.15
SYN Stealth Scan Timing: About 6.16% done; ETC: 17:02 (0:07:52 remaining)
SYN Stealth Scan Timing: About 8.60% done; ETC: 17:06 (0:10:48 remaining)

. . .

Once the scan is complete, we can bring our tcpdump process back into the foreground and stop it.

Bring it out of the background by typing:

fg

Stop the process by holding the control key and hitting “c”:

CTRL-C

You should now have two files in your ~/scan_results/syn_scan directory. One called packets, generated by the tcpdump run, and one generated by nmap called nmap.results.

Let's look at the nmap.results file first:

less ~/scan_results/syn_scan/nmap.results
~/scan_results/syn_scan/nmap.results
# Nmap 6.49BETA4 scan initiated Wed Aug 26 17:05:13 2015 as: nmap -sS -Pn -p- -T4 -vv --reason -oN /home/user/scan_results/syn_scan/nmap.results 198.51.100.15
Increasing send delay for 198.51.100.15 from 0 to 5 due to 9226 out of 23064 dropped probes since last increase.
Increasing send delay for 198.51.100.15 from 5 to 10 due to 14 out of 34 dropped probes since last increase.
Nmap scan report for 198.51.100.15
Host is up, received user-set (0.00097s latency).
Scanned at 2015-08-26 17:05:13 EDT for 2337s
Not shown: 65533 closed ports
Reason: 65533 resets
PORT   STATE SERVICE REASON
22/tcp open  ssh     syn-ack ttl 63
80/tcp open  http    syn-ack ttl 63
 
Read data files from: /usr/local/bin/../share/nmap
# Nmap done at Wed Aug 26 17:44:10 2015 -- 1 IP address (1 host up) scanned in 2336.85 seconds

This shows that port 22 and port 80 are open on the scanned host in order to allow SSH and HTTP traffic. We can also see that 65,533 ports were closed. Another possible result would be “filtered”. Filtered means that these ports were identified as being stopped by something along the network path. It could be a firewall on the target, but it could also be filtering rules on any of the intermediate hosts between the audit and target machines.

If we want to see the actual packet traffic that was sent to and received from the target, we can read the packets file back into tcpdump, like this:

sudo tcpdump -nn -r ~/scan_results/syn_scan/packets | less

This file contains the entire conversation that took place between the two hosts. You can filter in a number of ways.

For instance, to view only the traffic sent to the target, you can type:

sudo tcpdump -nn -r ~/scan_results/syn_scan/packets 'dst target_ip_addr' | less

Likewise, to view only the response traffic, you can change the “dst” to “src”:

sudo tcpdump -nn -r ~/scan_results/syn_scan/packets 'src target_ip_addr' | less

Open TCP ports would respond to these requests with a SYN packet. We can search directly for responses for this type with a filter like this:

sudo tcpdump -nn -r ~/scan_results/syn_scan/packets 'src target_ip_addr and tcp[tcpflags] & tcp-syn != 0' | less

This will show you only the successful SYN responses, and should match the ports that you saw in the nmap run:

Output

reading from file packets, link-type EN10MB (Ethernet)
17:05:13.557597 IP 198.51.100.15.22 > 198.51.100.2.63872: Flags [S.], seq 2144564104, ack 4206039348, win 29200, options [mss 1460], length 0
17:05:13.558085 IP 198.51.100.15.80 > 198.51.100.2.63872: Flags [S.], seq 3550723926, ack 4206039348, win 29200, options [mss 1460], length 0

You can do more analysis of the data as you see fit. It has all been captured for asynchronous processing and analysis.

Now that you have a good handle on how to run these tests, we can complete a similar process to scan for open UDP ports.

Once again, let's create a directory to hold our results:

mkdir ~/scan_results/udp_scan

Start a tcpdump capture again. This time, write the file to the new ~/scan_results/udp_scan directory:

sudo tcpdump host target_ip_addr -w ~/scan_results/udp_scan/packets

Pause the process and put it into the background:

CTRL-Z
bg

Now, we are ready to run the UDP scan. Due to the nature of the UDP protocol, this scan will typically take significantly longer than the SYN scan. In fact, it could take over a day if you are scanning every port on the system. UDP is a connection-less protocol, so receiving no response could mean that the target's port is blocked, that it was accepted, or that the packet was lost. To try to distinguish between these, nmap must re-transmit additional packets to try to get a response.

Most of the flags will be the same as we used for the SYN scan. In fact, the only new flag is:

• -sU: This tells nmap to perform a UDP scan.

If you are worried about the amount of time this test takes, you may only want to test a subset of your UDP ports at first. You can test only the 1000 most common ports by leaving out the -p- flag. This can shorten your scan time considerably. If you want a complete picture though, you'll have to go back later and scan your entire port range.

Because you are scanning your own infrastructure, perhaps the best option to speed up the UDP scans is to temporarily disable ICMP rate limiting on the target system. Typically, Linux hosts limit ICMP responses to 1 per second (this is typically a good thing, but not for our auditing), which means that a full UDP scan would take over 18 hours. You can check this setting on your target machine by typing:

sudo sysctl net.ipv4.icmp_ratelimit

Output

net.ipv4.icmp_ratelimit = 1000

The “1000” is the number of milliseconds between responses. We can temporarily disable this rate limiting on the target system by typing:

sudo sysctl -w net.ipv4.icmp_ratelimit=0

It is very important to revert this value after your test.

Be sure to write the results to the ~/scan_results/udp_scan directory. All together, the command should look like this:

sudo nmap -sU -Pn -p- -T4 -vv --reason -oN ~/scan_results/udp_scan/nmap.results target_ip_addr

Even with disabling ICMP rate limiting on the target, this scan took about 2 hours and 45 minutes during our test run. After the scan is complete, you should revert your ICMP rate limit (if you modified it) on the target machine:

sudo sysctl -w net.ipv4.icmp_ratelimit=1000

Bring the tcpdump process back into the foreground on your audit machine by typing:

fg

Stop the packet capture by holding control and hitting “c”:

CTRL-c

Now, we can take a look at the generated files.

The resulting nmap.results file should look fairly similar to the one we saw before:

~/scan_results/udp_scan/nmap.results

less ~/scan_results/udp_scan/nmap.results
~/scan_results/udp_scan/nmap.results
# Nmap 6.49BETA4 scan initiated Thu Aug 27 12:42:42 2015 as: nmap -sU -Pn -p- -T4 -vv --reason -oN /home/user/scan_results/udp_scan/nmap.results 198.51.100.15
Increasing send delay for 198.51.100.15 from 0 to 50 due to 10445 out of 26111 dropped probes since last increase.
Increasing send delay for 198.51.100.15 from 50 to 100 due to 11 out of 23 dropped probes since last increase.
Increasing send delay for 198.51.100.15 from 100 to 200 due to 3427 out of 8567 dropped probes since last increase.
Nmap scan report for 198.51.100.15
Host is up, received user-set (0.0010s latency).
Scanned at 2015-08-27 12:42:42 EDT for 9956s
Not shown: 65532 closed ports
Reason: 65532 port-unreaches
PORT    STATE         SERVICE REASON
22/udp  open|filtered ssh     no-response
80/udp  open|filtered http    no-response
443/udp open|filtered https   no-response
 
Read data files from: /usr/local/bin/../share/nmap
# Nmap done at Thu Aug 27 15:28:39 2015 -- 1 IP address (1 host up) scanned in 9956.97 seconds

A key difference between this result and the SYN result earlier will likely be the amount of ports marked open|filtered. This means that nmap couldn't determine whether the lack of a response meant that a service accepted the traffic or whether it was dropped by some firewall or filtering mechanism along the delivery path.

Analyzing the tcpdump output is also significantly more difficult because there are no connection flags and because we must match up ICMP responses to UDP requests.

We can see how nmap had to send out many packets to the ports that were reported as open|filtered by asking to see the UDP traffic to one of the reported ports:

sudo tcpdump -nn -P out -r ~/scan_results/udp_scan/packets 'udp and port 22'

You will likely see something that looks like this:

Output

reading from file /home/user/scan_results/udp_scan/packets, link-type EN10MB (Ethernet)
14:57:40.801956 IP 198.51.100.2.60181 > 198.51.100.15.22: UDP, length 0
14:57:41.002364 IP 198.51.100.2.60182 > 198.51.100.15.22: UDP, length 0
14:57:41.202702 IP 198.51.100.2.60183 > 198.51.100.15.22: UDP, length 0
14:57:41.403099 IP 198.51.100.2.60184 > 198.51.100.15.22: UDP, length 0
14:57:41.603431 IP 198.51.100.2.60185 > 198.51.100.15.22: UDP, length 0
14:57:41.803885 IP 198.51.100.2.60186 > 198.51.100.15.22: UDP, length 0

Compare this to the results we see from one of the scanned ports that was marked as “closed”:

sudo tcpdump -nn -P out -r ~/scan_results/udp_scan/packets 'udp and port 53'

Output

reading from file /home/user/scan_results/udp_scan/packets, link-type EN10MB (Ethernet)
13:37:24.219270 IP 198.51.100.2.60181 > 198.51.100.15.53: 0 stat [0q] (12)

We can try to manually reconstruct the process that nmap goes through by first compiling a list of all of the ports that we're sending UDP packets to using something like this:

sudo tcpdump -nn -P out -r ~/scan_results/udp_scan/packets "udp" | awk '{print $5;}' | awk 'BEGIN { FS = "." } ; { print $5 +0}' | sort -u | tee outgoing

Then, we can see which ICMP packets we received back saying the port was unreachable:

sudo tcpdump -nn -P in -r ~/scan_results/udp_scan/packets "icmp" |  awk '{print $10,$11}' | grep unreachable | awk '{print $1}' | sort -u | tee response

We can see then take these two responses and see which UDP packets never received an ICMP response back by typing:

comm -3 outgoing response

This should mostly match the list of ports that nmap reported (it may contain some false positives from lost return packets).

We can run some additional tests on our target to see if it is possible for nmap to identify the operating system running or any of the service versions.

Let's make a directory to hold our versioning results:

mkdir ~/scan_results/versions

We can attempt to guess the versions of services running on the target through a process known as fingerprinting. We retrieve information from the server and compare it to known versions in our database.

A tcpdump wouldn't be too useful in this scenario, so we can skip it. If you want to capture it anyways, follow the process we used last time.

The nmap scan we need to use is triggered by the -sV flag. Since we already did SYN and UDP scans, we can pass in the exact ports we want to look at with the -p flag. Here, we'll look at 22 and 80 (the ports that were shown in our SYN scan):

sudo nmap -sV -Pn -p 22,80 -vv --reason -oN ~/scan_results/versions/service_versions.nmap target_ip_addr

If you view the file that results, you may get information about the service running, depending on how “chatty” or even how unique the service's response is:

less ~/scan_results/versions/service_versions.nmap

shows:

~/scan_results/versions/service_versions.nmap

# Nmap 6.49BETA4 scan initiated Thu Aug 27 15:46:12 2015 as: nmap -sV -Pn -p 22,80 -vv --reason -oN /home/user/scan_results/versions/service_versions.nmap 198.51.100.15
Nmap scan report for 198.51.100.15
Host is up, received user-set (0.0011s latency).
Scanned at 2015-08-27 15:46:13 EDT for 8s
PORT   STATE SERVICE REASON         VERSION
22/tcp open  ssh     syn-ack ttl 63 OpenSSH 6.6.1p1 Ubuntu 2ubuntu2 (Ubuntu Linux; protocol 2.0)
80/tcp open  http    syn-ack ttl 63 nginx 1.4.6 (Ubuntu)
Service Info: OS: Linux; CPE: cpe:/o:linux:linux_kernel
 
Read data files from: /usr/local/bin/../share/nmap
Service detection performed. Please report any incorrect results at https://nmap.org/submit/ .
# Nmap done at Thu Aug 27 15:46:21 2015 -- 1 IP address (1 host up) scanned in 8.81 seconds

Here, you can see that the test was able to identify the SSH server version and the Linux distribution that packaged it as well as the SSH protocol version accepted. It also recognized the version of Nginx and again identified it as matching an Ubuntu package.

We can try to have nmap guess the host operating system based on characteristics of its software and responses as well. This works much in the same way as service versioning. Once again, we will omit the tcpdump run from this test, but you can perform it if you'd like.

The flag we need in order to perform operating system detection is -O (the capitalized letter “O”). A full command may look something like this:

sudo nmap -O -Pn -vv --reason -oN ~/scan_results/versions/os_version.nmap target_ip_addr

If you view the output file, you might see something that looks like this:

less ~/scan_results/versions/os_version.nmap

shows:

~/scan_results/versions/os_versions.nmap

# Nmap 6.49BETA4 scan initiated Thu Aug 27 15:53:54 2015 as: nmap -O -Pn -vv --reason -oN /home/user/scan_results/versions/os_version.nmap 198.51.100.15
Increasing send delay for 198.51.100.15 from 0 to 5 due to 65 out of 215 dropped probes since last increase.
Increasing send delay for 198.51.100.15 from 5 to 10 due to 11 out of 36 dropped probes since last increase.
Increasing send delay for 198.51.100.15 from 10 to 20 due to 11 out of 35 dropped probes since last increase.
Increasing send delay for 198.51.100.15 from 20 to 40 due to 11 out of 29 dropped probes since last increase.
Increasing send delay for 198.51.100.15 from 40 to 80 due to 11 out of 31 dropped probes since last increase.
Nmap scan report for 198.51.100.15
Host is up, received user-set (0.0012s latency).
Scanned at 2015-08-27 15:53:54 EDT for 30s
Not shown: 998 closed ports
Reason: 998 resets
PORT   STATE SERVICE REASON
22/tcp open  ssh     syn-ack ttl 63
80/tcp open  http    syn-ack ttl 63
No exact OS matches for host (If you know what OS is running on it, see https://nmap.org/submit/ ).
TCP/IP fingerprint:
OS:SCAN(V=6.49BETA4%E=4%D=8/27%OT=22%CT=1%CU=40800%PV=N%DS=2%DC=I%G=Y%TM=55
OS:DF6AF0%P=x86_64-unknown-linux-gnu)SEQ(SP=F5%GCD=1%ISR=106%TI=Z%CI=Z%TS=8
OS:)OPS(O1=M5B4ST11NW8%O2=M5B4ST11NW8%O3=M5B4NNT11NW8%O4=M5B4ST11NW8%O5=M5B
OS:4ST11NW8%O6=M5B4ST11)WIN(W1=7120%W2=7120%W3=7120%W4=7120%W5=7120%W6=7120
OS:)ECN(R=Y%DF=Y%T=40%W=7210%O=M5B4NNSNW8%CC=Y%Q=)T1(R=Y%DF=Y%T=40%S=O%A=S+
OS:%F=AS%RD=0%Q=)T2(R=N)T3(R=N)T4(R=Y%DF=Y%T=40%W=0%S=A%A=Z%F=R%O=%RD=0%Q=)
OS:T5(R=Y%DF=Y%T=40%W=0%S=Z%A=S+%F=AR%O=%RD=0%Q=)T6(R=Y%DF=Y%T=40%W=0%S=A%A
OS:=Z%F=R%O=%RD=0%Q=)T7(R=N)U1(R=Y%DF=N%T=40%IPL=164%UN=0%RIPL=G%RID=G%RIPC
OS:K=G%RUCK=G%RUD=G)U1(R=N)IE(R=N)
 
Uptime guess: 1.057 days (since Wed Aug 26 14:32:23 2015)
Network Distance: 2 hops
TCP Sequence Prediction: Difficulty=245 (Good luck!)
IP ID Sequence Generation: All zeros
 
Read data files from: /usr/local/bin/../share/nmap
OS detection performed. Please report any incorrect results at https://nmap.org/submit/ .
# Nmap done at Thu Aug 27 15:54:24 2015 -- 1 IP address (1 host up) scanned in 30.94 seconds

We can see that in this case, nmap has no guesses for the operating system based on the signature it saw. If it had received more information, it would likely show various percentages which indicate how the target machine's signature matches the operating system signatures in its databases. You can see the fingerprint signature that nmap received from the target below the TCP/IP fingerprint: line.

Operating system identification can help an attacker determine which exploits may be useful on the system. Configuring your firewall to respond to fewer inquiries can help to hinder the accuracy of some of these detection methods.

Testing your firewall and building an awareness of what your internal network looks like to an outside attacker can help minimize your risk. The information you find from probing your own infrastructure may open up a conversation about whether any of your policy decisions need to be revisited in order to increase security. It may also illuminate any gaps in your security that may have occurred due to incorrect rule ordering or forgotten test policies. It is recommended that you test your policies with the latest scanning databases regularity in order improve, or at least maintain, your current level of security.

To get an idea of some policy improvements for your firewall, check out this guide.

https://www.digitalocean.com/community/tutorials/how-to-test-your-firewall-configuration-with-nmap-and-tcpdump