Most operating systems employ a TCP timestamp behavior where the sender’s value reflects the number of clock ticks since the last reboot. A clock tick is a vague concept described in RFC 1323 as “The timestamp value to be sent is to be obtained from a (virtual) clock that we call the "timestamp clock". Its values must be at least approximately proportional to real time…”. Now, think about this in terms of security. A high TCP timestamp divulges that the host has not been rebooted in a while. Now, let’s say there is a patch released on MS Tuesday for a new Windows remote exploit. Further, installation of this patch requires a reboot. An attacker searching for victim hosts could gain some valuable reconnaissance just from a TCP timestamp if he/she could communicate with a potential target host via TCP.
OpenBSD must have seen the possible leakage of information from the TCP timestamp so they now randomize the first timestamp on every new TCP/IP session. They increment the timestamp in subsequent segments in the session to meet the standard of approximating the passage of time for accurate round trip time measurement (RTTM). But, they eliminate the possibility for the TCP timestamp to be used to reflect the uptime since last reboot.
Let’s take a look at the difference between the more conventional incremental Windows TCP timestamp and the randomized OpenBSD timestamp. I sent five SYNs in rapid succession to a Windows host first and then to an OpenBSD host to examine the TCP timestamp values in the returned SYN/ACK. I’ve edited the tcpdump output to contain only the pertinent information to save space. As you can see the Windows host 184.108.40.206 generates incremental TCP timestamp values.
Now, look at the OpenBSD random timestamp values from host 220.127.116.11.
While this is impressive in itself, I believe OpenBSD has relegated the use of TCP timestamps exclusively for RTTM and not for the almost useless Protection of Wrapped Sequence Numbers (PAWS) that distinguishes between old and new timestamps. As far as I’m concerned the RTTM is the only reason to support TCP timestamps so I’m pleased if this is the case. I say “if this is the case” since I don’t have an accessible OpenBSD to send my Scapy generated traffic so I have to believe that the Netcraft association of www. openbsd.org and www.bsd.org with OpenBSD/NetBSD OS is correct. My only hesitation is that there may be some kind of device that exists between the sending and receiving boxes that acts as a proxy or somehow permutes the TCP timestamp from the actual host. But, I tried two different hosts that reside on different networks to help bolster my confidence that I’m communicating with actual OpenBSD hosts.
My experiment is to try to get the receiving host to drop all segments after the initial SYN by assigning them a lower timestamp. Using Scapy, I place a timestamp value of 100 on the SYN and 0 on all subsequent ones. First, let’s look at how Windows handles this. It never acknowledges any data I send to it, echoes the expecected timestamp of "ecr 100", and even attempts to resend the SYN/ACK in the final segment to give me another chance to send an appropriate higher timestamp in my initial ACK. This is the expected behavior and conforms to RFC 1323 specification.
Conversely, take a look at the same traffic sent to an OpenBSD host 18.104.22.168. It happily accepts and echoes the old timestamp value of 0 and returns the requested web page, albeit in reverse order, meaning it accepted the segment with the old timestamp carrying the web request.
In an effort to corroborate the behavior above, I wanted to test another OpenBSD host – www.bsd.org - that belongs to a totally different network address block with different devices standing between my network and the web server. As you can see host 22.214.171.124 parrots this same behavior of ignoring the old timestamp.
Initially, I thought there might be something wrong with the traffic I was sending. I know some operating systems require you to echo the timestamp they issue in order to receive subsequent segments. I typically don’t do this because it’s a few more lines of code, but I added the code to echo the server’s timestamps and I still witnessed the behavior of OpenBSD ignoring old timestamps. If this is indeed the case, I think OpenBSD has made a good, and as usual, innovative decision to support only the useful features of the TCP timestamp.