Setting up wordpress sucks in 2025

How is setting up SSL going

Now I totally understand why personal blogs aren’t a thing any more and why Medium, Substack, etc grew so fast.

  • Setup PHP to run on IIS, which it doesn’t really want to do
  • Edit PHP conf files to enable a laundry list of sublibraries (which are probably 50kb of code total btw and should just be auto-included) required by WordPress
  • Setup SSL (this has gotten worse and worse)
  • Figure out how you are going to auto-renew SSL (this is a thing now apparently)
  • Setup the basic ability to send email (this used to be a standard feature of IIS, but in the modern web ecosystem has become incredibly complicated)
  • All WordPress plugins seem to be bloatware with built-in upsells. Since plugins are arbitrary PHP code snippets they can do annoying things like put nag screens into your WP dashboard.