Sam Roelants

SSLstrip and HSTS

SSL/TLS and Man-in-the-middle attacks

The biggest issue with all cryptography, both symmetric and public-key, is its susceptibility to man-in-the-middle (MITM) attacks. Simply put, Alice and Bob want to communicate securely by setting up a shared secret key they will use to encrypt their messages. But, a malicious third party (Eve) intercepts the messages, pretends to be Bob when talking to Alice and pretends to be Alice when talking to Bob. Instead of Alice setting up a secret connection with Bob, Eve sets up a secret connection with both Alice and Bob, and relays all the communications. Eve ends up controlling the entire communication.

man in the middle attack

Public-key crytpography doesn’t have a solution for this problem, and the only way we’ve found around this attack is the mechanism of certificates, signed by (reliable) third parties, that Alice and Bob can use to prove that they are in fact who they claim they are. In order to prevent the signatures to be forged by yet another MITM attack, the public keys of most Certificate Authorities (CAs) that are needed to verify the certificate signatures typically come preinstalled with most modern browsers.

So, certificate verification is a big step in SSL/TLS, the protocol that all browsers use for secure communication (whenever you see https:// in your browser URL bar).

302 redirects and SSL strip

While it seems like certificates completely eliminate the chance of MITM attacks (unless the browser or CA private keys are compromised), there is still some surface area for attacks, like SSL strip. The basis for this attack lies in the fact that most websites, say your email hosts website, is usually accessed over http. The website then responds with an http 302 Found code, along with the location where the browser should go looking for the resource. Websites use this mechanism to redirect all visits over http to the https served website instead. That is, when you go to, you’ll automatically end up at, probably without the user ever noticing it.

And there’s the rub: unless you’re a very security-concious person, you wouldn’t even notice whether or not you’ve been redirected to the https version of the website. Although browsers are really stepping up to give clear warning of websites that are served up over insecure http

Supposing you visit your mail provider’s website over http – let’s be honest, we all do --, a man in the middle could intercept this traffic and essentially stop the redirect from happening. Instead, the man in the middle could set up a https connection with your mail provider, but simply downgrade from https to http before sending the response back to the user. To the user, the only noticeable difference would be that the connection remains over http instead of https, but other than that, the user experience is identical.

ssl stripping attack

Certificates are of no help here, because the user’s browser never even realizes it should be communicating over TLS!

At this point, of course, we’re back to our classical MITM scenario: the malicous eavesdropper has access to all the unencrypted messages coming from the unsuspecting user.


Does this mean TLS and certificates are essentially useless? Not entirely, and there are definitely ways to somewhat mitigate this vulnerability. One easy thing you could do as a web host is enabling HTTP Strict Transport Security (HSTS). It’s a specific https header that the server can set on its response packets that intstructs the browser to only every allow the site to be accessed over https for a given duration of time (eg, a year). Because the header can only be set over https, it means that the user must have established an https connection with the webserver at least once for HSTS to take effect. This means the initial visit is still vulnerable to SSL stripping attacks, but it greatly decreases the risk.