Frank
Tuesday night. Blown past my self-imposed deadline on a Docker stack update for Scooby. One container wasn’t routing correctly through my reverse proxy, and I was three cups of coffee into what should’ve been a 20-minute fix. I pulled up the Caddy docs, found the directive I needed, dropped it into my Caddyfile, reloaded the service, and it just worked.
I didn’t fully understand why. But it worked.
That moment locked in something I’ve been sitting on for a while: the tools I trust and the tools I use are genuinely not the same list. And the more I think about it, the more I think that’s exactly how it should be.
Most people in the homelab and IT space would say that’s backwards. You should understand the tools you trust. You should trust the tools you use. Close the gap. That sounds reasonable. It’s also not how any of this actually works, and pretending otherwise keeps a lot of people from being honest about their own workflows.
The Tool You Trust Isn’t Always the One You Understand
Here’s my honest confession: I trust Caddy more than I trust NGINX, even though I spent years with NGINX and I’ve only been running Caddy for a while. The reason isn’t technical mastery. It’s track record.
Caddy has failed me exactly zero times since I migrated away from NGINX Proxy Manager. Zero. It handles my SSL certs without me babysitting them. The config syntax is clean enough that even when I don’t know exactly what I’m doing, I can usually figure it out by reading it out loud. When something breaks, the logs are readable by a human being, which is not something I can say about everything running in my homelab.
Trust, for me, isn’t a measure of understanding. It’s a measure of how many times something has not let me down when it mattered. That’s a different thing entirely.
I understand PowerShell pretty well. I’ve been writing it for years. I know how it thinks. But I don’t trust it the way I trust Caddy, because PowerShell has humiliated me in front of my own terminal more times than I can count. A well-placed semicolon in the wrong spot. A pipeline that behaves differently than the docs say. An Exchange cmdlet that works perfectly in one tenant and throws a cryptic error in another. I understand it, and it still bites me.
Here’s the part most people don’t want to say out loud: understanding a tool and trusting a tool are two completely separate things. You can know exactly how something works and still not bet on it. And you can trust something you couldn’t fully explain if your job depended on it.
The Tools I Reach For Without Thinking
On the other side of that gap: the tools I use constantly that I would never call trustworthy.
Puppeteer is the clearest example. I built SunoHarvester around it because it does something I need it to do, automate browser interactions in ways that nothing else handles as cleanly. But Puppeteer is a temperamental piece of software. It breaks between Node.js versions. Selectors stop working because a site updated its DOM structure. Timeouts behave inconsistently depending on whether your machine is breathing funny that day.
I use it. I wouldn’t call it reliable. SunoHarvester is still unfinished partly because the tool underneath it requires constant babysitting, and I never fully know what’s going to work until I run it and find out.
PHP is another one. I’ve written real applications in it, Crumble is running on PHP and MySQL right now, and it works fine. But if you asked me to recommend PHP to someone starting a new project today, I’d hesitate. I use it because I know it well enough to be productive, and for certain kinds of simple web apps it’s still the fastest path from nothing to something. I wouldn’t say I trust it the way I trust, say, Claude when I’m working through a gnarly problem. I just reach for it out of habit and familiarity.
That’s the thing about “use” vs. “trust.” Use is often about momentum. You reach for what’s already in your hand.
Why Closing That Gap Isn’t Always the Right Move
Here’s where I’m going to lose some people: I don’t think you should always close the gap.
The conventional wisdom says if you trust a tool, you should know it inside and out. Audit it. Understand every layer. If you can’t explain it, you shouldn’t rely on it. That’s a perfectly good philosophy for a college course. In practice, you’d never ship anything.
I’ve been doing IT for 28 years. I trust DNS. I would fail a quiz on the full RFC spec for DNS. I trust TLS certificates. My understanding of the full handshake process is functional but not expert. I trust Docker to do what it does without fully grasping every decision the networking subsystem is making when I spin up a new container with a custom bridge network.
What I actually do, and what I think most experienced people actually do, is calibrate trust based on observed failure rate, blast radius when it does fail, and how fast I can recover. Caddy gets deep trust because when it fails, the failure is obvious and the fix is usually a one-line change. Puppeteer gets used but not trusted because when it fails, the failure is invisible until you check the output.
That’s a more honest framework than “do you understand it?” Understanding is nice. Failure behavior is what matters at 11 PM when something stops working and you’ve got three other things you need to finish.
The tools I’d stake a production system on are not always the tools I’d teach someone. The tools I’d teach are not always the ones I reach for. And the ones I reach for are not always the ones I’d write a post recommending.
Knowing which category a tool lives in, that’s the actual skill. Not mastery of any single one of them.
