Transitioning to TLS

tl;dr: Migrating old content and infrastructure to TLS is still f’ing hard. If you are using CloudFlare, see “How do I fix the infinite redirect loop error after enabling Flexible SSL with WordPress?“.

After the recent push by many in the standards community to transition our sites to TLS, I decided to move my blog over to TLS. The push is driven the the need to generally try to make the Web more secure + we are trying to move the Web forward by requiring TLS for certain APIs (e.g., Service Workers).

This is not the first time I’ve moved this blog to use TLS.

Early attempt

The first time I did this was a few years ago when I became interested in encryption. During that time, AFAIK, in order to have a SSL certificate you needed to have a static IP address. Furthermore, there was no intermediary services, like StartSSL or CloudFlare, to provide sites with essentially free certificates. Doing the transition to SSL with my host (DreamHost) was fairly straight forward, but quite expensive for me at the time (I was a student or a junior engineer at the time). I don’t recall the exact numbers, but it was effectively something like $25/year for a static IP and then probably something like $50/year for the cert. This on top of the 10/year for the domain + $150 something/year I pay for hosting. Eventually, the cost became a burden to me: only a small handful of people ever visit this site (I don’t know how many as I don’t use analytics our of respect for my visitors) – but I just didn’t feel it was worth the cost so I abandoned it.

This was pre-Snowden, so I was fairly naive to the dragnet activities of the likes of the those assholes at the NSA. I also didn’t understand that, even if your site’s content is harmless, it serves as a data-point in a visitors history. By using TLS, one obscures the navigational trail: they may know you looked at, but not what you were reading. It can help a little.


More recently, in light of all the bad shit that’s happening in the world, and prompted by Anne van Kesteren, I decided to re-encrypt this site. However, this time around I had a very negative experience trying to transition my personal blog to TLS.

After complaining to Anne about the costs, he pointed me to CloudFlare with the claims about it being free. The setup experience with CloudFlare was pretty straight forward: put a few things into a form and then go and tell DreamHost that the DNS values had changed. No big deal… but then things started to get fun.

Firstly, although my site started working straight away over TLS, I had to wait 4 days for the certificate to actually say it was for “”- during which time browsers accessing my site over HTTPS would see the red warning screen (effectively blocking anyone visiting the site over HTTPS). Thankfully, I had left plain old HTTP access enabled.

Once my certificate was actually granted and working, I decided to disable HTTP altogether. I did this by telling WordPress that this site’s URL was now “” – which immediately triggered a cascade of shit. Firstly, the site went into an infinite redirect loop and the whole site became inaccessible. I tried to revert this change in WordPress’ database, but it didn’t seem to help. I then tried to revert various things – but also didn’t work so I just left it be as I had other work to do.

I was offline for about 1 week, then thankfully WordPress issued an update. This seemed to fix things somewhat: at least the site started working again over HTTP. However, switching to HTTPS is still quite broken – the admin section is still completely broken. It won’t load styles because WordPress is too stupid to realize it is running over HTTPS instead of HTTP.

Anyway, and I’m still struggling with various things. Migrating old content and infrastructure to TLS is still hard.

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