The setup that broke my Friday afternoon
I was checking my own SEO. I typed “quizwrap” into Google. My site, QuizWrap — a free quiz-maker for students — showed up as the very first result. Great.
I clicked it.
A Ho’oponopono prayer counter loaded.
That’s a completely different app I run on the same server, and visitors looking for QuizWrap were landing on it instead. Worse, I quickly noticed a related issue: visiting https://smartdisha.co.in/ directly threw a TLS certificate error in the browser.
Two bugs, both on the same VPS, both involving the nginx reverse proxy that fronts everything. I sat down with Claude (Anthropic’s coding agent inside Claude Code) and we dug in together. What follows is the story of that debugging session — both the technical findings and what it was like to pair-debug with an AI.
The architecture (and a quick glossary)
A quick mental model so the rest of this makes sense.
A single VPS hosts three sites behind one system nginx — a popular web server that, in this setup, acts as a reverse proxy: a traffic cop sitting in front that takes incoming HTTPS requests and forwards them to the right internal app.
- quizwrap.com — my quiz app
- prayer.quizwrap.com — a small prayer counter
- smartdisha.co.in — a separate site on the same box
Some traffic flows through a CDN before reaching origin, some doesn’t. Each domain has its own free Let’s Encrypt TLS certificate (the thing that makes the little padlock icon appear in your browser), and nginx is configured with one server block per domain.
A few terms I’ll keep using:
- TLS — the encryption layer behind HTTPS. The “S” in HTTPS.
- Certificate — a small file that proves a server owns the domain it claims to. Browsers reject the connection if the cert doesn’t match the domain.
- SNI (Server Name Indication) — the most important term in this whole post. When your browser opens a TLS connection to
smartdisha.co.in, it whispers the hostname it wants before the encryption is set up, so the server knows which certificate to present. One server can host many domains on the same IP, and SNI is how it picks the right cert. If SNI says one thing and the server returns the wrong cert, the browser shows a security warning and refuses to load the page. - Server block — nginx’s term for “the config chunk that handles requests for one domain.” Each domain has one (or several).
server_namedirective — the line inside a server block that lists which hostnames that block is responsible for. If no block claims a hostname, nginx silently picks a default block as a fallback.
Bug #1: www.quizwrap.com was serving the prayer app
The detective work
Before touching anything, Claude pulled response headers from both URLs in parallel:
curl -sI https://www.quizwrap.com/
curl -sI https://smartdisha.co.in/Two response bodies came back with identical fingerprints:
| www.quizwrap.com | smartdisha.co.in | |
|---|---|---|
ETag |
"69d2087a-332" |
"69d2087a-332" |
Content-Length |
818 | 818 |
Last-Modified |
same date | same date |
| Title in body | Ho'oponopono Counter |
Ho'oponopono Counter |
(An ETag is a unique fingerprint a web server attaches to a file’s response — like a checksum. Two responses with the same ETag are byte-for-byte the same file.)
Same file, served to two different domains. Now we knew it was an nginx routing question, not a DNS or CDN issue.
Reading the configs over SSH
I had Claude SSH into my server (passwordless key auth — read-only operations, no sudo) and dump the three nginx configs. The first thing it spotted:
# /etc/nginx/sites-available/quizwrap.com
server {
server_name quizwrap.com;
...
}server_name quizwrap.com — not quizwrap.com www.quizwrap.com. There was no server block anywhere on the box claiming www.quizwrap.com. When a request arrived at my server saying “this is for www.quizwrap.com”, nginx had no rule that named that hostname, so it fell back to the first SSL block in alphabetical order — the one for prayer.quizwrap.com, which is what serves the prayer app.
That’s how a Google click on www.quizwrap.com ended up rendering Ho’oponopono. nginx was doing exactly what it was told; what it was told just didn’t include the www version of my domain.
The fix
A one-liner:
sudo sed -i 's/server_name quizwrap.com;/server_name quizwrap.com www.quizwrap.com;/' \
/etc/nginx/sites-available/quizwrap.com
sudo nginx -t && sudo systemctl reload nginxA test confirmed it:
HTTP/2 200
last-modified: Sun, 30 Nov 2025 15:42:27 GMT ← quizwrap build, not the prayer one
<title>QuizWrap - FREE Study Quiz Maker for Students</title>Then a defensive follow-up: re-issue the Let’s Encrypt cert to cover the www version too, so the cert chain stays internally consistent. (A single cert can list multiple hostnames in a field called the Subject Alternative Name, or SAN — that’s just “the list of domains this cert is valid for.”) One certbot command added www.quizwrap.com to the cert. Done.
Bug #1: 5 minutes from “what is happening” to “fixed.”
Bug #2 was not like that.
Bug #2: smartdisha.co.in and the certificate that wouldn’t come right
The symptom
Browsers refused https://smartdisha.co.in/ with a cert error. openssl s_client showed why:
$ echo | openssl s_client -servername smartdisha.co.in -connect smartdisha.co.in:443 2>/dev/null \
| openssl x509 -noout -subject -ext subjectAltName
subject=CN = prayer.quizwrap.com
DNS:prayer.quizwrap.comThe browser asked for smartdisha.co.in (via SNI), and the server handed back a certificate that says “I’m prayer.quizwrap.com.” That’s a name mismatch, so the browser refuses the connection — you’ve probably seen the resulting “Your connection is not private” error page. At first I thought the fix was going to be just as quick as the www one.
It wasn’t.
Two hours of dead ends
Here’s the parade of “that should have fixed it”:
- Re-issue the cert?
sudo certbot --nginx -d smartdisha.co.in— certbot reported there was an existing cert and offered to reinstall. Reinstalled. No change. Browser still got prayer’s cert. - Maybe nginx didn’t reload cleanly.
sudo systemctl reload nginx. No change. - Inspect the cert file directly.
sudo openssl x509 -in /etc/letsencrypt/live/smartdisha.co.in/fullchain.pem \ -noout -subject -ext subjectAltName subject=CN = smartdisha.co.in DNS:smartdisha.co.inThe file on disk was correct. nginx just wasn’t serving it.
- Maybe the workers cached an old cert.
sudo systemctl restart nginx. No change. - Check
nginx -Tfor the loaded config. The smartdisha SSL block was fully loaded, with the rightserver_name, the rightlisten 443 ssl;, and the right cert path. Everything looked correct. Still no change.
At one point I checked ps and noticed three nginx master processes — two with nginx -g daemon off; (the Docker-container telltale) and one system nginx. Claude initially flagged this as the smoking gun: maybe a Docker container was intercepting TLS. We confirmed via ss -tlnp that the system nginx was actually the only thing on port 443; the Docker nginxes were just internal app servers behind it. Wrong turn — but a reasonable one.
My moment of skepticism
I sent Claude a screenshot of my DNS panel with the message:
“Before we go chase our tail. Check the configuration attached.”
This was the right instinct. I was tired of theories that weren’t panning out. Stepping back to verify a load-bearing assumption — is the request path for this domain actually what we think it is? — confirmed we were looking at the right place, but it could just as easily have caught us going the wrong way for another hour.
Lesson: when you’re three theories deep and none have stuck, your AI assistant doesn’t always notice it’s in a loop. Pushing back is your job.
The breakthrough: probing SNI directly
Claude wrote a small loop that asked nginx, in plain English: “If a browser tells you it wants hostname X, which certificate do you hand back?” It does this once for each domain on the box.
ssh my-server 'for sni in <each-hostname-on-the-box>; do
printf "SNI=%-30s -> " "$sni"
echo | openssl s_client -servername "$sni" -connect localhost:443 2>/dev/null \
| openssl x509 -noout -subject 2>/dev/null
done'SNI=smartdisha.co.in -> CN = prayer.quizwrap.com ❌
SNI=www.quizwrap.com -> CN = quizwrap.com ✓
SNI=quizwrap.com -> CN = quizwrap.com ✓
SNI=prayer.quizwrap.com -> CN = prayer.quizwrap.com ✓
SNI=nonexistent.example.com -> CN = prayer.quizwrap.com (default fallback)There it was. smartdisha.co.in was being treated identically to a totally unknown hostname. It wasn’t a cert problem at all — the cert file on disk was perfectly fine. nginx just wasn’t recognizing smartdisha.co.in as a hostname it knew about. Both unknown hostnames and smartdisha.co.in fell through to the same default fallback block (prayer, which is alphabetically first), which is why both got prayer’s cert.
The actual root cause
With that clue, Claude re-read all three nginx configs side-by-side and found the only structural difference:
| Block | IPv6 listen | IPv4 listen |
|---|---|---|
| prayer | listen [::]:443 ssl ipv6only=on; |
listen 443 ssl; |
| quizwrap | listen [::]:443 ssl; (dual-stack) |
listen 443 ssl; |
| smartdisha | — missing — | listen 443 ssl; |
A bit of background to read that table: every server on the internet has two kinds of addresses available — older IPv4 (the familiar 1.2.3.4 style) and newer IPv6 (the longer ::1 style). nginx’s listen directive tells it which addresses to accept connections on. listen 443 ssl; means “IPv4 only.” listen [::]:443 ssl; means “IPv6,” but on Linux it can also quietly accept IPv4 connections at the same time — that’s what “dual-stack” means.
quizwrap’s listen [::]:443 ssl; (without ipv6only=on) creates one of these dual-stack sockets. Internally, nginx groups server blocks by which socket they’re attached to, and uses that grouping to decide who handles each incoming connection. smartdisha, lacking any IPv6 listen line of its own, ends up in a different group than the dual-stack one, and inside that group the prayer block (alphabetically first) becomes the default catch-all. Even though smartdisha’s server block is loaded and looks correct, the grouping means SNI lookups for smartdisha.co.in arrive at a group where smartdisha isn’t listed — and fall back to prayer.
Subtle, weird, and exactly the kind of thing nginx -t (the config syntax checker) won’t catch, because the syntax is fine.
The fix
Make smartdisha’s listen directives match the others:
sudo sh -c '
cp /etc/nginx/sites-available/smartdisha.co.in /etc/nginx/sites-available/smartdisha.co.in.bak
sed -i "/^ listen 443 ssl; # managed by Certbot$/i\\ listen [::]:443 ssl;" \
/etc/nginx/sites-available/smartdisha.co.in
nginx -t && systemctl reload nginx && echo DONE
'Re-running the SNI probe afterwards:
SNI=smartdisha.co.in -> CN = smartdisha.co.in ✓curl https://smartdisha.co.in/ succeeded with full TLS validation, no -k flag needed. The browser was happy.
What it was actually like to debug this with an AI
A few things stood out about the collaboration that I want to share.
Claude was great at the things I’m bad at. It pulled response headers from two domains in parallel, parsed cert subjects out of openssl s_client output, and noticed immediately that two responses had the same ETag — something I’d have read past. The structured diff between three nginx configs at the end (the listener-table comparison) was exactly the kind of thing my eyes glaze over after the second config file.
I was great at the things Claude is bad at. When we got stuck on Bug #2, Claude proposed three theories in a row, each plausible, none correct. The Docker-container theory in particular was a confidently-stated wrong answer. I knew that side of my own infrastructure well enough to be unimpressed. My push-back (“before we chase our tail”) was what reset the direction.
Security boundaries actually got enforced. When I offered Claude my sudo password to speed things up, it explicitly refused and explained why (the password would be in the chat transcript, in shell process listings, and a single leak compromises the whole server). It walked me through the alternatives — running the destructive commands myself in my own terminal, or scoping a passwordless sudoers rule for nginx-related commands only. Reading the full advice, I ended up just running each sudo command in my own shell and pasting the result. Slower, but at no point did a privileged credential cross a boundary it shouldn’t.
Transparency mattered. Halfway through Bug #2 I told Claude “I can’t see the commands you’re executing on my server.” It immediately listed every SSH command it had run and committed to printing each new command before executing it. That changed the dynamic — it stopped feeling like Claude was off doing things in the dark and started feeling like a teammate sharing their screen.
Knowing when to escalate to a one-shot fix. After multiple roundtrips of “paste this, paste that,” I asked Claude to drive over SSH so I could stop copy-pasting. It moved the read-only diagnostics to its own SSH connection and packaged the one mutating step into a single sudo block I could paste once and approve once. The friction of the back-and-forth dropped massively.
Lessons that generalise
A few things I’m taking away from this:
- Identical
ETags across two domains = the same file is being served. If two of your sites unexpectedly look the same, that single header probably solves the mystery before you read a line of config. server_nameis a registration, not just a label. If a hostname isn’t named in any block, nginx won’t error — it’ll silently pick a default and serve someone else’s content.nginx -tpassing means valid syntax. It does not mean what you intended. All three configs in this story passednginx -twith no warnings while half-broken.- Mixing
listen [::]:443 ssl;(dual-stack) andlisten 443 ssl;(IPv4-only) across server blocks is a footgun. Either go all-dual-stack or all-with-ipv6only=on. Mixing changes the listener topology in ways that affect SNI dispatch. - The
openssl s_client -servername X -connect Y:443probe is a debugging superpower. It’s a one-line command that simulates exactly what a browser does — say “I want hostname X” via SNI, and see which certificate the server returns. Whenever an HTTPS-served domain is misbehaving, this probe will often tell you the answer in five lines. - Pair-debugging with an AI works best when you stay in the loop. Treat its theories as drafts, not conclusions. Push back when you smell drift. Make it show its work.
The whole session was somewhere between two and three hours. By the end my SEO problem was gone, my secondary domain’s TLS was clean, and I had a much better mental model of how nginx makes SNI decisions across mixed-listener configurations. Worth the afternoon.
Total commands run on the server during this session: about 30. Total commands run with sudo: 5. Total credentials shared with the AI: zero.