How To Test your Firewall Configuration with Nmap and Tcpdump
Introduction
Setting up a firewall for your infrastructure is a great way to provide some basic security for your services. Once you've developed a policy you are happy with, the next step is to test your firewall rules. It is important to get a good idea of whether your firewall rules are doing what you think they are doing and to get an impression of what your infrastructure looks like to the outside world.
In this guide, we'll go over some simple tools and techniques that you can use to validate your firewall rules. These are some of the same tools that malicious users may use, so you will be able to see what information they can find by making requests of your servers.
Prerequisites
In this guide, we will assume that you have a firewall configured on at least one server. You can get started building your firewall policy by following one or more of these guides:
- Iptables
- UFW
- FirewallD
In this guide, we will call the server containing the firewall policies you wish to test the target. In addition to your target, you will also need to have access to a server to test from, located outside of the network that your firewall protects. In this guide, we will use an Ubuntu 14.04 server as our auditing machine.
Once you have a server to test from and the targets you wish to evaluate, you can continue with this guide.
The Tools We Will Use to Test Firewall Policies
There are quite a few different tools that we can use to test our firewall policies. Some of them have overlapping functionality. We will not cover every possible tool. Instead, we will cover some general categories of auditing tools and go over the tools we will be using in this guide.
Packet Analyzers
Packet analyzers can be used to watch all of the network traffic that goes over an interface in great detail. Most packet analyzers have the option of operating in real time, displaying the packets as they are sent or received, or of writing packet information to a file and processing it at a later time. Packet analysis gives us the ability to see, at a granular level, what types of responses our target machines are sending back to hosts on the open network.
For the purposes of our guide, we will be using the tcpdump
tool. This is a good option because it is powerful, flexible, and rather ubiquitous on Linux systems. We will use it to capture the raw packets as we run our tests in case we need the transcript for later analysis. Some other popular options are Wireshark (or tshark
, its command line cousin) and tcpflow
which can piece together entire TCP conversations in an organized fashion.
Port Scanners
In order to generate the traffic and responses for our packet analyzer to capture, we will use a port scanner. Port scanners can be used to craft and send various types of packets to remote hosts in order to discover type of traffic the server accepts. Malicious users often use this as a discovery tool to try to find vulnerable services to exploit (part of the reason to use a firewall in the first place), so we will use this to try to see what an attacker could discover.
For this guide, we will use the nmap
network mapping and port scanning tool. We can use nmap
to send packets of different types to try to figure out which services are on our target machine and what firewall rules protect it.
Setting Up the Auditing Machine
Before we get started, we should make sure we have the tools discussed above. We can get tcpdump
from Ubuntu's repositories. We can also get nmap
with this method, but the repository version is likely out of date. Instead, we will install some packages to assist us in software compilation and then build it ourselves from source.
Update the local package index and install the software if it is not already available. We will also purge nmap
from our system if it is already installed to avoid conflicts:
- sudo apt-get update
- sudo apt-get purge nmap
- sudo apt-get install tcpdump build-essential libssl-dev
Now that we have our compilation tools and the SSL development library, we can get the latest version of nmap
from the download page on the official site. Open the page in your web browser.
Scroll down to the "Source Code Distribution" section. At the bottom, you will see a link to the source code for the latest version of nmap
. At the time of this writing, it looks like this:
Right-click on the link and copy the link address.
Back on your auditing machine, move into your home directory and use wget
to download the link you pasted. Make sure to update the link below to reflect the most recent version you copied from the site:
- cd ~
- wget https://nmap.org/dist/nmap-6.49BETA4.tar.bz2
Decompress the file you downloaded and move into the resulting directory by typing:
- tar xjvf nmap*
- cd nmap*
Configure and compile the source code by typing:
- ./configure
- make
Once the compilation is complete, you can install the resulting executables and supporting files on your system by typing:
- sudo make install
Confirm your installation by typing:
- nmap -V
The output should match the version you downloaded from the nmap
website:
OutputNmap version 6.49BETA4 ( https://nmap.org )
Platform: x86_64-unknown-linux-gnu
Compiled with: nmap-liblua-5.2.3 openssl-1.0.1f nmap-libpcre-7.6 nmap-libpcap-1.7.3 nmap-libdnet-1.12 ipv6
Compiled without:
Available nsock engines: epoll poll select
Next, we will create a directory where we can store our scan results:
- mkdir ~/scan_results
To make sure that you get clean results, exit out of any sessions you might have open between your auditing system and the target system. This includes SSH sessions, any HTTP(S) connections you may have established in a web browser, etc.
Scan your Target for Open TCP Ports
Now that we have our server and files ready, we will begin by scanning 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.
Setting Up the Packet Capture
Before we scan, we will set up tcpdump
to capture the traffic generated by the test. This will help us 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
Now, 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.
Run the 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 thatnmap
will perform if no scan type is given, but we will include it here to be explicit.-Pn
: This tellsnmap
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 tellsnmap
to check every available port.-T4
: This sets a timing profile fornmap
, 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 tellsnmap
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.
-6
flag to your commands. Because most of the prerequisite tutorials do not accept IPv6 traffic, we will be skipping IPv6 for this guide. 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 (my test run lasted about forty minutes). You will see results begin to print that look something like this:
OutputStarting 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)
. . .
Stop the tcpdump Packet Capture
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
Analyzing the Results
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
# 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
The highlighted area above contains the main results of the scan. We can see 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:
Outputreading 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.
Scan your Target for Open UDP Ports
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.
Setting Up the Packet Capture
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
Run the UDP Scan
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 connectionless 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 retransmit 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 tellsnmap
to perform a UDP scan.
Speeding up the UDP Test
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
Outputnet.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.
Running the 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
Stop the tcpdump Packet Capture
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
Analyzing the Results
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:
- less ~/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 -Q out -r ~/scan_results/udp_scan/packets 'udp and port 22'
You will likely see something that looks like this:
Outputreading 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 -Q out -r ~/scan_results/udp_scan/packets 'udp and port 53'
Outputreading 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 -Q 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 -Q 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).
Host and Service Discovery
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
Discovering the Versions of Services on the Server
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
# 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.
Discovering the Host Operating System
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
# 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.
Conclusion
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.
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