One of the things I’ve been less than happy with in my time at WordPress.com is that premium users using their own domains didn’t get SSL, whereas free users using something.wordpress.com did. There are perfectly logical technical reasons for that, but I had seriously considered moving elsewhere just to get SSL.
It turns out though that WordPress.com now supports SSL on custom domains, thanks to the LetsEncrypt initiative. The TL;DR version is that LetsEncrypt provides free certificates, supported by all modern browsers, that can be auto-generated using a command line utility. In fact LetsEncrypt is what I’d have most likely ended up using if I’d gone elsewhere.
How close I came to going elsewhere can be demonstrated by the DNS weirdness that some readers might have seen last night. I actually did cancel my WordPress.com premium renewal, and signed up with a traditional hosting provider. Thankfully that was only on a month-to-month deal (though to be fair to them, their signup process was slick and painless), and WordPress.com support were extremely helpful in un-cancelling the renewal I’d asked them to cancel about six hours previously!