The use of secure connections using HTTPS as the default means, or even the only means, to connect to web servers is increasing. It is being pushed from both sides: from the bottom up by client distributions and plugins, and from the top down by organisations such as Google. However, there are potential technical hurdles that might lock some clients out of the modern web. This paper seeks to measure and precisely quantify those hurdles in the wild. More than three million measurements provide statistically significant evidence of degradation. We show this through a variety of statistical techniques. Various factors are shown to influence the problem, ranging from the client's browser, to the locale from which they connect.