Serving WordPress over HTTPS with Caddy Server

The Caddy server is a relatively new, easy-to-use server written in the Go programming language. It is very buzzword compliant. But, the nicest thing about it, in my opinion, is that it sets up SSL/TLS (Secure Sockets Layer/Transport Layer Security) certificates automatically from Let’s Encrypt to let you serve a site with HTTPS by default. The project is open source and the certificates are free.

Of course, WordPress is a very popular blogging platform. Caddy provides some guidance on getting WordPress up and running on the server. However, it wasn’t enough for me. Here’s some step-by-step guidance on how I got it working on some of my own self-hosted sites.

How this Blog Disappeared (and Reappeared) Again

Some of you may have noticed that this blog disappeared again for awhile. It was on purpose this time. As I noted in an earlier post, getting WordPress to work on this host has been a bit of a chore. I got tired of doing updates and installs of plugins and such manually. It was not particularly hard, just tiresome. And then some warnings about particularly nasty XSS bugs appeared. At that time, I took the blog offline until I had some time to deal with things.


Now, I love WordPress. It’s easy to use and easy to administer. Except when it isn’t. I run multiple sites on multiple servers. For the most part, they are trouble free. Except one site. This site. (Update 16 Aug 2017: This was referring to my site on CloudAtCost.) You see, I can’t seem to load plugins or new themes or updates for some reason. I run the same OS (Ubuntu 14.

A New Theme

This probably has no interest to anyone but me, but you may notice a change in the blog theme today. I’ve been dissatisfied with the typography of the blog for quite some time. Today I set out to try to find a theme that had better typography. Man, what a mess! There are a zillion WordPress themes out there. Some awful, but many quite good. However, finding a minimalist theme intended for writing and reading is surprisingly difficult.

Something New. Comments!

Well, it’s been a long time coming and I’m still a little unsure about it, but starting now, this site will allow comments. I’ve explained why I didn’t allow them before, but I’m adding Disqus-powered discussions to the blog. We’ll see how that goes. If everything that comes in is just spam, I’ll disable comments again. If comments are useful, civil and on topic, they will remain. And we’ll see if anyone thinks any of this stuff is interesting enough to comment on in the first place.

Moving Old Posts

Since I’m going through the setup again, I thought I would start out with some older posts from other systems (the few that remain). Don’t pay much attention to the dates.

So, Dr. Clark. We meet again!

Well, here we are again. You, me, and WordPress. It seems like I go through this setup a lot. Over the years, I’ve tried other blogging platforms, and even toyed with the idea of creating one of my own for fun like one of my heroes, Brian Carper(Broken Link). But I just keep coming back here. Why do I ever leave? There are really a couple of reasons. I do this a lot because of hardware and backup failures.