HSTS Preloading with Azure Web Apps

In previous posts, I’ve talked about implementing web security features such as HTTPS, CSP, HPKP and HSTS. Almost all of these are things we can configure ourselves within our web applications responses to client requests however one of these features, HSTS requires a little more work to fully implement.

HSTS is a technology of two halves. HTTP Strict Transport Security (HSTS) is a feature which allows a website to instruct the client that it should never be downgraded to HTTP and should only ever request and receive data from the site over HTTPS. We can easily implement this, in the case of Windows and IIS, using a web.config file outbound rewrite rule which I covered in the previous post, Working Hard on Web Security.

The trouble is, this is only half the battle. If a client repeatedly visits your site, their browser will know as a result of previous visits to always use HTTPS due to having previously seen the HSTS header but what about new visitors? What happens if your site is victim of a downgrade attack between you implementing HTTPS and HSTS and the first time a user visits? Their browser doesn’t know it should be using HSTS already so we have a problem.

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