I should also mention that while we try to be as transparent as possible in all our work (including holding community consultations around all major legal policies and providing frequent updates on our work), there are very limited situations where public discussions could actually hurt free access to Wikipedia. If you have thoughts about the evolving censorship landscape, feel free to email me directly, if possible via encrypted email.
I find the secrecy surrounding the HTTPS rollout to be odd (To put it mildly).
What are we worried about. A censor who follows wikimedia-l, but not the press release the WMF issued?
All the technical details are public (The git repo is public. Not to mention the whole fact we're using https is going to be painfully obvious when you visit the site, and its in https). We aren't doing anything surprising, we are in the process of simply following what many people consider best practices. We've publicly stated our intention to do this for years now. And its pretty obvious what the next steps of the deployment are going to be. The only thing really being kept secret is the timetable, and which specific projects are up next.
-- bawolff