Wikipedia's Switch To HTTPS Has Successfully Fought Government Censorship (vice.com)
Determining how to prevent acts of censorship has long been a priority for the non-profit Wikimedia Foundation, and thanks to new research from the Harvard Center for Internet and Society, the foundation seems to have found a solution: encryption. From a report: HTTPS prevents governments and others from seeing the specific page users are visiting. For example, a government could tell that a user is browsing Wikipedia, but couldn't tell that the user is specifically reading the page about Tiananmen Square. Up until 2015, Wikipedia offered its service using both HTTP and HTTPS, which meant that when countries like Pakistan or Iran blocked the certain articles on the HTTP version of Wikipedia, the full version would still be available using HTTPS. But in June 2015, Wikipedia decided to axe HTTP access and only offer access to its site with HTTPS. [...] The Harvard researchers began by deploying an algorithm which detected unusual changes in Wikipedia's global server traffic for a year beginning in May 2015. This data was then combined with a historical analysis of the daily request histories for some 1.7 million articles in 286 different languages from 2011 to 2016 in order to determine possible censorship events. [...] After a painstakingly long process of manual analysis of potential censorship events, the researchers found that, globally, Wikipedia's switch to HTTPS had a positive effect on the number censorship events by comparing server traffic from before and after the switch in June of 2015.
It's a little worse than that. Because the url's are different, the Chinese government has blocked the zh.wikipedia.org but not the en.wikipedia.org, presumably because most Chinese people can not read English too a high enough level. They should move the language into the end part of the URL i.e. wikipedia.org/en/some-article
The web client will reuse the connection to the server, and to a 3rd-party observer it will all look like one massive blob of data so that all they could really get out of it is the content length of the whole thing, which due to gzip compression (which is enabled for Wikipedia, I checked), caching of resources, etc, means it will vary considerably from one fetch of a given page to the next.
If that isn't enough, http servers and TLS ciphers themselves actively hide the length of the content they transmit with techniques such as padding and adding additional random bytes to the beginning or end of a HTTPS transmission.
All up, I'd say this vector would be pretty much impossible to exploit.
Windows is a bonfire, Linux is the sun. Linux only looks smaller if you lack perspective.