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Nmap Network Scanning

Detecting Packet Forgery by Firewall and Intrusion Detection Systems

Previous sections mentioned that some firewall and intrusion detection systems can be configured to forge packets as if they came from one of the protected systems behind the device. TCP RST packets are a frequent example. Load balancers, SSL accelerators, network address translation devices, and certain honeynets can also lead to confusing or inconsistent results. Understanding how Nmap interprets responses helps a great deal in piecing together complex remote network topologies. When Nmap reports unusual or unexpected results, you can add the --packet-trace option to see the raw packets upon which Nmap based its conclusions. In perplexing situations, you may have to go even further and launch custom probes and analyze packets with other tools such as Nping and Wireshark. The goal is often to find inconsistencies that help you understand the actual network setup. The following sections describe several useful techniques for doing so. While most of these tests do not involve Nmap directly, they can be useful for interpreting unexpected Nmap results.

Look for TTL Consistency

Firewalls, load balancers, NAT gateways, and similar devices are usually located one or more hops in front of the machines they are protecting. In this case, packets can be created with a TTL such that they reach the network device but not the end host. If a RST is received from such a probe, it must have been sent by the device.

During one informal assessment, I scanned the network of a large magazine publisher over the Internet (you may remember them from the section called “SOLUTION: Scan a Large Network for a Certain Open TCP Port”). Almost every IP address showed port 113 closed. Suspecting RST forgery by a firewall, I dug a bit deeper. Because it contained open, closed, and filtered ports, I decided to focus on this host in particular:

# nmap -sS -Pn -T4 mx.chi.playboy.com
Starting Nmap ( http://nmap.org )
Nmap scan report for mx.chi.playboy.com (216.163.143.4)
Not shown: 998 filtered ports
PORT    STATE  SERVICE
25/tcp  open   smtp
113/tcp closed auth

Nmap done: 1 IP address (1 host up) scanned in 53.20 seconds

Is port 113 really closed, or is the firewall spoofing RST packets? I counted the distance (in network hops) to ports 25 and 113 using the custom traceroute mode of the free hping2 utility, as shown in Example 10.22. I could have used the faster Nmap --traceroute option to do this, but that option did not exist at the time.

Example 10.22. Detection of closed and filtered TCP ports

# hping2 -t 5 --traceroute -p 25 -S mx.chi.playboy.com
[combined with results from hping2 -i 1 --ttl \* -p 25 -S mx.chi.playboy.com]
5->TTL 0 during transit from 64.159.2.97 (ae0-54.mp2.SanJose1.Level3.net)
6->TTL 0 during transit from 64.159.1.34 (so-3-0-0.mp2.Chicago1.Level3.net)
7->TTL 0 during transit from 200.247.10.170 (pos9-0.core1.Chicago1.level3.net)
8->TTL 0 during transit from 200.244.8.42 (gige6-0.ipcolo1.Chicago1.Level3.net)
9->TTL 0 during transit from 166.90.73.205 (ge1-0.br1.ord.playboy.net)
10->TTL 0 during transit from 216.163.228.247 (f0-0.b1.chi.playboy.com)
11->No response
12->TTL 0 during transit from 216.163.143.130 (fw.chi.playboy.com)
13->46 bytes from 216.163.143.4: flags=SA seq=0 ttl=52 id=48957 rtt=75.8 ms

# hping2 -t 5 --traceroute -p 113 -S mx.chi.playboy.com
[ results augmented again ]
5->TTL 0 during transit from 64.159.2.97 (ae0-54.mp2.SanJose1.Level3.net)
6->TTL 0 during transit from 64.159.1.34 (so-3-0-0.mp2.Chicago1.Level3.net)
7->TTL 0 during transit from 200.247.10.170 (pos9-0.core1.Chicago1.level3.net)
8->TTL 0 during transit from 200.244.8.42 (gige6-0.ipcolo1.Chicago1.Level3.net)
9->TTL 0 during transit from 166.90.73.205 (ge1-0.br1.ord.playboy.net)
10->TTL 0 during transit from 216.163.228.247 (f0-0.b1.chi.playboy.com)
11->Nothing
12->46 bytes from 216.163.143.4: flags=RA seq=0 ttl=48 id=53414 rtt=75.0 ms

This custom traceroute shows that reaching open port 25 requires 13 hops. 12 hops away is a firewall in Chicago, helpfully named fw.chi.playboy.com. One would expect different ports on the same machine to be the same hop-distance away. Yet port 113 responds with a RST after only 12 hops. That RST is being forged by fw.chi.playboy.com. Since the firewall is known to forge port 113 responses, those packets should not be taken as an indicator that a host is available at a given IP address. I found available hosts by ping scanning the network again, using common probe types such as ICMP echo requests (-PE) and SYN packets to ports 22 and 80 (-PS22,80), but omitting any ping probes involving TCP port 113.

Look for IP ID and Sequence Number Consistency

Every IP packet contains a 16-bit identification field that is used for defragmentation. It can also be exploited to gain a surprising amount of information on remote hosts. This includes port scanning using the Nmap idle scan technique, traffic estimation, host alias detection, and much more. It can also help to detect many network devices, such as load balancers. I once noticed strange OS detection results when scanning beta.search.microsoft.com. So I launched hping2 SYN probes against TCP port 80 to learn what was going on. Example 10.23 shows the results.

Example 10.23. Testing IP ID sequence number consistency

# hping2 -c 10 -i 1 -p 80 -S beta.search.microsoft.com
HPING beta.search.microsoft.com. (eth0 207.46.197.115): S set, 40 headers
46 bytes from 207.46.197.115: flags=SA seq=0 ttl=56 id=57645 win=16616
46 bytes from 207.46.197.115: flags=SA seq=1 ttl=56 id=57650 win=16616
46 bytes from 207.46.197.115: flags=RA seq=2 ttl=56 id=18574 win=0
46 bytes from 207.46.197.115: flags=RA seq=3 ttl=56 id=18587 win=0
46 bytes from 207.46.197.115: flags=RA seq=4 ttl=56 id=18588 win=0
46 bytes from 207.46.197.115: flags=SA seq=5 ttl=56 id=57741 win=16616
46 bytes from 207.46.197.115: flags=RA seq=6 ttl=56 id=18589 win=0
46 bytes from 207.46.197.115: flags=SA seq=7 ttl=56 id=57742 win=16616
46 bytes from 207.46.197.115: flags=SA seq=8 ttl=56 id=57743 win=16616
46 bytes from 207.46.197.115: flags=SA seq=9 ttl=56 id=57744 win=16616

Looking at the sequence of IP ID numbers (in bold), it is clear that there are really two machines sharing this IP address through some sort of load balancer. One has IP ID sequences in the range of 57K, while the other is using 18K. Given this information, it is no wonder that Nmap had trouble settling on a single operating system guess. They may be running on very different systems.

Similar tests can be performed on other numeric fields, such as the TCP timestamp option or the initial sequence number returned by open ports. In this particular case, you can see that the TCP window size and TCP flags also give the hosts away.

The Bogus TCP Checksum Trick

Another handy trick for determining whether an IDS or firewall is spoofing response packets is to send probes with a bogus TCP checksum. Essentially all end hosts check the checksum before further processing and will not respond to these corrupt packets. Firewalls, on the other hand, often omit this check for performance reasons. We can detect this behavior with the --badsum option, as shown in Example 10.24.

Example 10.24. Finding a firewall with bad TCP checksums

# nmap -sS -p 113 -Pn --badsum google.com

Starting Nmap ( http://nmap.org )
Warning: Hostname google.com resolves to 3 IPs. Using 64.233.187.99.
Nmap scan report for jc-in-f99.google.com (64.233.187.99)
PORT    STATE  SERVICE
113/tcp closed auth

Nmap done: 1 IP address (1 host up) scanned in 0.44 seconds

From Example 10.24 we can infer that there is some sort of network device, perhaps a firewall, that is handling packets destined to google.com on port 113 without verifying TCP checksums. Normally, an end host will silently drop packets with bad TCP checksums and we will see a filtered port instead of a closed one. --badsum will also use bad checksums for other protocols on top of IP, including UDP, ICMP, and IGMP.

This technique, along with other reasons for deliberately sending packets with malformed checksums, is further described in Phrack 60, article 12 by Ed3f. While this is sometimes a useful technique, there are several caveats to consider:

  1. Many modern firewalls now verify TCP checksums (at least when determining whether to respond to a packet) to avoid leaking this information. So this technique is more useful for proving that a --badsum probe response was sent by a firewall (or other device with an incomplete TCP stack) than for proving that a filtered --badsum probe was dropped by an end host.

  2. Using --badsum does not guarantee that packets will be sent with bad checksums on all platforms. On a few systems, the kernel or the network card performs the checksum calculation and insert the correct value, overwriting the desired bad value. One way to make sure this isn't happening to you is to use a remote machine to sniff the packets you are sending. For example, when sniffing with tcpdump, packets with bad TCP checksums will be indicated like [bad tcp cksum aa79 (->ab79)!]. Another approach is to do a normal SYN scan against one of your hosts (with at least one open port). Then do the same scan with --badsum. If the same ports are still shown as open, then --badsum probably isn't working for you. Please report the problem as described in the section called “Bugs”.

Round Trip Times

When a firewall forges a probe response, that response usually returns slightly sooner than a response from the true destination host would. After all, the firewall is usually at least one hop closer. It is also optimized for quickly parsing and processing packets, and does little else. The destination host, on the other hand, may be so busy running applications that it takes several milliseconds longer to respond to a probe. Thus, a close comparison of round trip times can often give away firewall shenanigans.

A challenge with this technique is that the time discrepancy between a firewall response and a true target response may be a fraction of a millisecond. Normal round trip time variances may be greater than that, so sending just two probes (one that solicits a response known to be from the target host, and one suspect response that may be from the firewall) is rarely enough. Sending a thousand of each probe type cancels out most of the RTT variance so that fundamental differences can be discerned. This doesn't need to take all that long—nping with the options -c 1000 --rate 20 sends a thousand probes in less than a minute. From those results, calculate the median rather than using the average it gives you. This prevents enormous times (such as from a lost response that is retransmitted two seconds later) from skewing the data. Do the thousand probes once or twice more to determine how consistent the results are. Then try the same with the suspect probe and compare the two. If the times are exactly the same to the last significant digit, the same host is likely sending both responses. If you consistently see that one probe type responds more quickly than the other, packet forgery may be responsible.

This method isn't perfect. A time discrepancy could be caused by any number of other factors than a firewall. It is still a valuable technique, as detecting network anomalies such as packet forgery is like proving a court case. Every little bit of evidence helps toward reaching a conclusion. The discrepancy may even lead to more interesting discoveries than firewall forgery. Maybe certain ports on the target are being redirected to a honeynet to better study attacks.

Close Analysis of Packet Headers and Contents

It is surprising how many elements can differ in even a small TCP header. Refer to Chapter 8, Remote OS Detection for dozens of subtle details that can be indicative of a different OS. For example, different systems respond with different TCP options, RST packet text, type of service values, etc. If there are several systems behind a load balancer, or the packets are being sent by firewall or intrusion detection systems, the packets will rarely match exactly.

An excellent tool for dissecting packet headers is Wireshark because it can break the header out into individual fields and provide textual descriptions of the binary contents of the packet. The trick to comparing packets is to collect one packet you think may be from a firewall and another packet of the same type from the target host or target operating system. Two packet types you are likely to be able to collect are TCP reset packets and ICMP error packets. By using Nping or the --scanflags Nmap option it should be possible to elicit responses with different IP, TCP, or ICMP headers.

Unusual Network Uniformity

When response packets are sent by a firewall, they are often more uniform than would be expected from clusters of individual machines. While scanning the magazine company discussed in the previous TTL-checking section, I found that hundreds of sequential-IP machines responded with a RST to port 113. In a real cluster of machines, you would expect at least a couple to be offline at a given time. Additionally, I was unable to elicit any other type of response from most of these addresses. This suspicious result led me to do the TTL tests which showed that the fw.chi host was actually spoofing the RST packets.

A firewall doesn't even have to spoof packets to give itself away. Another common firewall configuration is to drop packets to specific ports. Many ISPs filter Windows ports 135, 139, and 445 to reduce the spread of worms. If a large number of adjacent live hosts show up with the same set of filtered ports, a network firewall is the likely culprit. After determining which ports are being filtered by a firewall, you can often map out how many hosts are protected by those firewall rules by scanning many netblocks for those filtered ports. This can lead to the discovery of any accidental holes or the organization's DMZ (demilitarized zone) which typically hosts public services and has far looser firewall rules.

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