The use of HTTPS as 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 statistical techniques, in particular Rasch analysis, which also shows that various factors influence the problem ranging from the client’s browser, to their locale.