Why won’t my website send emails? (an emotional journey)

WordPress | Tech Fails | AI Workflows

3 min read

Not tooting my own horn here, but I am the designated tech support of my family. Netflix problems? Call Veronica. “The printer isn’t working”? Veronica. Setting up Starlink? I’ve done it every year for the past 3 years my parents have gone on holidays. I’m even the unofficial tech support at work — there is a genuine let’s see if Veronica knows before we walk down to IT protocol.

I have built four websites from scratch.

And on Thursday night, a contact form nearly broke me.

The website was essentially finished. The contact form looked beautiful. The newsletter signup looked beautiful. One last ten-minute job before launch: make the form actually work. And that’s when the thought arrived — where do these emails actually go?

The answer, it turns out, is nowhere. Websites don’t magically send email. Nobody tells you this. You need something called SMTP, which I discovered when my site greeted me with “No mailer configured,” as if that’s a sentence a normal person understands.

My first plan was “I’ll just use Gmail, I don’t need another inbox.” ChatGPT — the beautiful wingwoman that she is — talked me into buying one professional mailbox instead: hello@notanothersidequest.com. $37 for the year, on brand, forwards to Gmail. Fine. Fine. I immediately felt better.

That feeling lasted about fifteen minutes. Because then, a popup: Cannot forward emails because DKIM isn’t configured.

DKIM. Never heard of her.

The instructions said “log into Titan,” so I spent thirty-plus minutes trying to log into the Titan admin panel. Password wrong. Reset it. Different login? Wrong account entirely? Full spiral. Eventually I realised I wasn’t even supposed to be in there. The instructions just assumed I ran a mail server. I do not run a mail server. I run a blog with a pretty contact form.

Which brings me to the real villain: DNS. I hate DNS so, so much. I have cried actual tears over DNS on previous websites — twice — and DMARC once almost ended me entirely. My working mental model of email was: SMTP → DKIM → SPF → MX → DMARC → ??? → magic.

Then, mid-breakdown, my wingwoman finally explained it in a way my brain accepted. Forget the acronyms. Your website is a house:

• DNS is the street directory — it tells everyone where your house is.
• MX is the mailbox — “deliver mail here.”
• SPF is the guest list — who’s allowed to send letters as you.
• DKIM is the wax seal — every letter gets stamped so the receiver knows it’s really you.
• DMARC is the security guard — “seal’s broken? Bin it.”
• SMTP is the postman who actually carries the letter.

And suddenly the entire Titan mess made sense: Titan doesn’t own my street directory — WordPress does. Titan can only ask me to update it. That one sentence is the difference between a ten-minute job and ninety minutes of despair. Most documentation assumes you already know it. Most of us don’t.

So, armed with my new house metaphor, I marched into my DNS records to configure DKIM and… it was already configured. It had been sitting there the whole time. I’d spent the best part of an hour solving a problem that had already been solved. Peak side quest behaviour.

“There is a very big difference between ‘I don’t understand this’ and ‘no one has explained this in a way that makes sense.'”

Surely that’s the end? No. SMTP setup: host, port, TLS, username, password — all correct. Authentication failed. This is the point where I typed, and I quote, “I really like how you’re still hyping me up right now Chatty because I could really cry.”

The actual fix was one innocent little setting buried in Titan: Enable Titan on other apps. One click. That was it. That was the whole thing.

The full emotional journey, timestamped:

8:00pm — “I’ll just connect my contact form.”
8:10pm — “Should I use Gmail?”
8:25pm — buys professional email 💸
8:40pm — DKIM??? 😭
8:50pm — logging into the wrong admin panel for absolutely no reason
9:00pm — “OMG THE DKIM RECORD WAS ALREADY THERE.”
9:10pm — SMTP Authentication Failed.
9:15pm — “I could really cry.” 🥺
9:20pm — EMAIL SENT SUCCESSFULLY 🎉

I shouted. Out loud. I briefly considered framing the test email.

Here’s the thing I actually want you to take from this: being good with technology doesn’t mean you automatically understand servers — and that’s okay. There is a very big difference between “I don’t understand this” and “no one has explained this in a way that makes sense.” Thursday night was ninety minutes of the second one wearing the first one’s outfit.

Oh — and I know I promised you the “how I got here” post next. This is not that post. I got distracted by a side quest and wrote this one instead.

You’ll get used to this.