My scariest crash was caused my a new WordPress database “upgrade,” but that was a one-time thing. Drupal’s security fixes, in contrast, are a perennial pain. They are core updates, and that means bringing down the site, manually replacing files, and praying for the best. I was hoping that moving up to Drupal 8 would make life easier, but far from it. My transition to 8 has been very bumpy, and the fun isn’t over yet.