I just set up SSLTLS on my web site. Everything can be had via https://wingolog.org/, and things appear to work. However the process of transitioning even a simple web site to SSL is so clownshoes bad that it’s amazing anyone ever does it. So here’s an incomplete list of things that can go wrong when you set up TLS on a web site.

Now you start to add secure features to your web app, safe with the idea you have SSL. But better not forget to mark your cookies as secure, otherwise they could be leaked in the clear, and better not forget that your website might also be served over HTTP. And better check up on when your cert expires, and better have a plan for embedded browsers that don’t have useful feedback to the user about certificate status, and what about your CA’s audit trail, and better stay on top of the new developments in security! Did you read it? Did you read it? Did you read it?

It’s a wonder anything works. Indeed I wonder if anything does.

Without any doubt this is one of the better(?) rants about SSL/TLS that I’ve read recently. And given my own recent experiences in setting up SSL/TLS on another site I entirely empathize: it was a horrible experience that involved tracking down what was causing things to break, when they were breaking, and how to remedy them. It was a non-trivial learning experience and that was a very simple site. Large sites….well, I shudder to consider the work entailed in securing them.

(As a sidenote: yes, SSL/TLS is broken. But it adds friction to mass surveillance processes and at little cost to the visitor of websites/users of web services. It’s a pain for those delivering content, but that’s a pain that it’s arguably appropriate for those content providers to bear.)

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