I've been a long-time user of Sinatra as well as Rails. About 8 years ago or so I decided to move all of my sites onto Sinatra and made a simple file-backed CMS

I've been a long-time user of Sinatra as well as Rails. About 8 years ago or so I decided to move all of my sites onto Sinatra and made a simple file-backed CMS that has scaled quite well over the years. The drawbacks of the approach have been having to write a lot of methods and classes from scratch to handle certain processing data (there is no actual database) but the end result has been something quite bulletproof and scalable to a point, and the experience implementing those features (like TLS, sessions, helpers, etc) has been quite valuable. However, my needs are starting to grow and I think soon we will have to move off of the old framework onto something new as our business requirements grow more complex.