Not knowing Middleman, I initially read the title (currently "Three Middleman Hacks We’re Using On This Site") as "Three Man-in-the-Middle hacks We're Using on This Site.
For some reason I read it as "Mediterranean" first, but by the time I got the visual buffet of Mediterranean dishes and trying to cope with one hacking such a thing, I also began to see it as MITM hacks.
It's really only confusing in this particular context, or to be precise, this particular sentence. Similarly, "Metropolitan Transportation Authority Invests Heavily in Rails" doesn't really make "Ruby on Rails" a particularly confusing project name.
Well, to be fair, Middleman translates authoring files (sass, yaml, haml, etc) into ready-to-publish static assets. It can also be wired to liveroad so that it instantly updates what you see in the browser. In that workflow, the name really makes sense to me.
Middleman is actually a really great piece of software. I've used it on multiple projects, and it's really great for what it does.
When all you have to do is hand a set of static files off to the client, Middleman allows you to use your favorite technologies like Sass, and comes combined with LiveReload (which is a nice time-saver).
It's also very Sinatra-esque, which I greatly approve of.
Risky click!