Confession time: this website has been running on autopilot since 2024. Not “lightly maintained” — I mean abandoned garage project levels of neglect. WordPress was four major versions behind. Plugins were so old they were leaving passive-aggressive notes in my dashboard. My security scanner was reporting 29 vulnerabilities, which is the website equivalent of your smoke detector chirping for two years straight.
You know how it goes. Life happens, projects stack up, and the website that was supposed to bring fellow tech geeks together quietly gathers digital dust.
So tonight I tried something very on-brand for this blog: I let an AI do it.
The Setup
I’ve been using Claude (Anthropic’s AI) with its Chrome extension, which lets it actually drive the browser — clicking buttons, reading pages, navigating dashboards — while I watch it happen live on my screen. Think of it like handing your keyboard to a very patient friend who happens to have read every WordPress documentation page ever written.
My job? Click “Allow” on a couple of permission prompts and provide moral support. (I’m told this is called “supervising.”)
What It Actually Did
Here’s the punch list from tonight, all done through my own browser while I watched:
- Checked the backups first. Before touching anything, it verified my host had a fresh backup from the night before. Safety net confirmed, then the wrenching started. This is the part I always skip when I do it myself, which is exactly why I shouldn’t do it myself.
- Updated WordPress core from 6.5.8 all the way to 7.0.1 — a jump of four major versions in one shot.
- Updated eight plugins, including some scary ones: my forum software (wpForo) made a major 2.x to 3.x leap, Elementor jumped to 4.x, and WooCommerce vaulted from 9.4 to 10.9.
- Updated the theme — and because past-me had the rare good sense to use a child theme, none of my customizations were touched. Past-me deserves a beer for that one.
- Ran all the database migrations that WooCommerce and Elementor demanded afterward.
- Verified everything still worked — homepage, shop, and forum all checked after each risky step, not just at the end.
Total time: about an hour, most of which was me squinting at permission prompts and going outside to think.
The Part That Surprised Me
What got me wasn’t the speed — it was the order of operations. Backup first. Plugins before core. Verify the site renders between each risky step. Decline the random “activate our new AI features!” popups instead of clicking through them. It worked the way you’d want a careful sysadmin to work, and it narrated what it was doing the entire time so I never wondered what was happening on my own site.
It even caught things I’d forgotten about — like the expired payment card on my hosting account that was one renewal cycle away from taking the whole site offline. Two years of chirping smoke detectors, silenced in one evening.
Should You Do This?
If your site has been sitting neglected like mine was, here’s my honest take:
- Backups are non-negotiable. AI or no AI, nothing gets updated until you have a restore point.
- Watch it work. The Chrome extension approach means everything happens in front of you, in your own browser. You’re the supervisor, and you can stop it at any time.
- Child themes will save your bacon. Years later, that one decision made tonight’s theme update a non-event.
- The scary red vulnerability count is mostly just “you’re out of date.” Most of those 29 CVEs evaporated the moment everything got current.
We are, as I keep saying around here, living in the FUTURE. Tonight the future updated my website while I had a smoke.
Got questions about the setup, or thinking about trying it on your own dusty WordPress install? Drop a comment below — you know I love this stuff.