Common Pitfalls When Hosting Your Own Podcast Feed (Even with ChatGPT’s Help)

Everyone’s using AI to spin up servers these days — but the real lessons come from the errors ChatGPT didn’t predict. Here’s what actually broke, and how I fixed it.

I wanted to host my own podcast RSS feed from a FastAPI app on Azure and figured ChatGPT could walk me through it.
Spoiler: it did — but only after I hit every invisible wall the Internet can throw at you.

From DNS records that don’t resolve to Let’s Encrypt timeouts and HTTP verbs your app doesn’t support, these are the mistakes that don’t show up in neat AI-generated tutorials — and what you actually need to know when you do this for real.

⚠️ Mistake #1 — Assuming “the server is running” means “the world can reach it”

When ChatGPT told me “your server is running on port 8080,” I thought that meant I could just open a browser and go to http://<public-ip>:8080.

Nope.
Azure VMs come wrapped in multiple layers of security:

• VM’s own OS firewall (UFW or firewalld)

• Azure Network Security Group (NSG)

• And sometimes, a load balancer in front

If any one of those blocks inbound 8080, you’re invisible to the Internet.
The fix? Explicitly open the port:

az vm open-port --resource-group <RG> --name <VM> --port 8080

and double-check that your app binds to 0.0.0.0, not 127.0.0.1.

🧩 Mistake #2 — Forgetting about DNS propagation

When I added podcast.yusizhang.com in Cloudflare, I expected it to work instantly.
Ping said otherwise:
ping: cannot resolve podcast.yusizhang.com: Unknown host

Cloudflare DNS isn’t always instant, and sometimes you accidentally create a CNAME instead of an A record.
Also, if you leave the orange proxy cloud on, your server might not even be reachable during certificate setup.

Lesson learned:

• Use an A record, not a CNAME.

• Set Proxy status = DNS only (gray) until SSL works.

• Check propagation with dig podcast.yusizhang.com +short.

🔒 Mistake #3 — HTTPS verification failing due to Azure firewall

Let’s Encrypt failed with a cryptic timeout:

Timeout during connect (likely firewall problem)

The real issue? I had opened port 8080 for my app, but not port 80 for HTTP verification.
Certbot uses a temporary challenge file on port 80 to prove you own the domain.
Until I ran:

az vm open-port --resource-group <RG> --name <VM> --port 80

the certificate request kept failing.

Once I did — 💥 instant success.

🧱 Mistake #4 — Nginx reverse proxy confusion

ChatGPT’s Nginx config looked simple:

location / {
  proxy_pass http://127.0.0.1:8000;
}

…but what wasn’t obvious at first was that Nginx doesn’t automatically serve HTTPS just because it’s installed.
Certbot configures SSL for you only after it successfully verifies the domain — so if the challenge fails, you’re left with half a setup and a broken redirect.

Lesson: always test http://yourdomain/feed.xml first before trying to force HTTPS.

🧠 Mistake #5 — HEAD requests returning 405 errors

After everything was working, I proudly ran:

curl -I https://podcast.yusizhang.com/feed.xml

…and got:

HTTP/1.1 405 Method Not Allowed
allow: GET

Turns out FastAPI only defines a GET route by default, so HEAD requests (which tools like curl use for checking status) failed.

It didn’t break Apple Podcasts — but it’s a good example of how *“looks fine in browser” ≠ “standards-compliant server.”

The fix was easy:

@app.head(”/feed.xml”)
async def feed_head():
    return Response(headers={”Content-Type”: “application/rss+xml”})

Problem solved.

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If you’re thinking of self-hosting your podcast feed — do it.
Just remember: the magic isn’t in following ChatGPT’s steps; it’s in learning why those steps fail.

And if you’re wondering in why am I hosting a podcast on a VPS, checkout the Github project