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Andrew Ayer


Why Man-in-the-Middle Detection is Overrated

Last week, Nick Sullivan launched, a website that purports to tell you whether or not your HTTPS connection is being intercepted by a man-in-the-middle (MitM). uses Caddy's HTTPS MitM Detection Feature, which implements the techniques described in this paper. Basically, Caddy compares the browser name and version number advertised by the User-Agent header to the properties of the TLS handshake initiated by the client (e.g. ciphersuites). If the TLS handshake doesn't match the known properties of the purported browser, then the TLS handshake was probably not initiated by the browser, but by a man-in-the-middle. Caddy's documentation suggests that you could display an error message if a MitM is detected. displays either a green "No MITM!" page, or a red "Likely MITM!" page.

Unfortunately, there is a significant and intractable shortcoming to MitM detection: a MitM can defeat the detection by making its TLS implementation work exactly like that of the browser it's proxying, or at least similar enough that the differences are not observable by the server. You should assume a malicious MitM (one designed to steal data) will conceal itself this way. And if websites start displaying errors when a MitM is detected, you should expect the makers of commercial TLS interception devices (e.g. Bluecoat) to respond by making their interception devices indistinguishable from browsers.

We need to stop obsessing over MitM detection. In addition to server-side MitM detection, another recurring idea is to apply HTTP Public Key Pinning (HPKP) to certificates issued by private certificate authorities (e.g. those used by MitM devices), or to display a special icon in the browser when an HTTPS connection uses a private certificate authority. These proposals are barking up the wrong tree. Short of protocol or implementation vulnerabilities, there are only two ways a TLS connection can be intercepted without the consent of the server operator: one, an unauthorized certificate is issued by a publicly-trusted certificate authority, or two, a private certificate authority has been added to the client's trust store. (I assume the website is using HSTS, which prevents certificate errors from being bypassed.) For the first case, we have Certificate Transparency, which is better than even pie-in-the-sky MitM detection, since it detects rogue certificates even if they are never used. And the second case can only happen if the client's trust store is modified. At that point, the client's security should be considered compromised, as the ability to modify the trust store typically implies the ability to do much worse, such as install spyware that monitors and exfiltrates everything you do, without so much as touching a TLS connection. It's pointless to try to ensure end-to-end encryption when the security of an endpoint is in doubt.

That said, there is one potential benefit to MitM detection. Despite claiming to improve security, many commercial TLS interception devices actually harm security by using TLS client implementations that are vastly inferior to those of modern browsers. For instance, they use old, insecure ciphers, or even fail to validate the certificate. If the makers of commercial TLS interception devices are forced to emulate the TLS implementations of browsers to avoid detection, they may end up improving their security in the process. However, if this is the goal, MitM detection is rather superfluous: servers might as well just check for insecure attributes of the connection and raise an error if found, MitM or not. After all, MitMs are not the only perpetrators of poor TLS security; there are plenty of old and insecure browsers out there as well. Jeff Hodges' How's My SSL, which recently launched a subscription service that lets you use it on your own site, is one example of this approach.

Hi, I'm Andrew. I'm the founder of SSLMate, which makes SSL certificates easy through automation, great software, and friendly support.

I blog about security, PKI, Linux, and more. If you liked this post, check out my other posts or subscribe to my Atom feed.

My email address is I'm AGWA at GitHub and @__agwa on Twitter.


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