A client’s booking emails were failing and so I donned my Sherlock Holmes hat and set out to find the problem. Well, I sat here and tapped a few keys, to see if we could find a date.
I remember being fascinated by my mother’s typewriter and how it worked. The carbon copies, the effortless grace, the way everything had to be typed exactly — so that would have been about 1975. When I was 11.
No one told the recipient the letter had not been sent.
A book of eight first class stamps just cost me £14.40.
I found 12 emails that had never arrived — 7 booking confirmations that had been paid for, and 5 replies to people who’d filled in the enquiry form. Every one of them recorded as sent, and not one delivered.
Nothing had told the owner: no bounce came back, no alert appeared anywhere, and the provider never wrote to say anything was wrong. From the inside the system worked, because everything anyone could see said it did.
When a booking confirmation doesn’t arrive, the customer doesn’t email you to say her booking confirmation didn’t arrive — she assumes she isn’t booked in, or that you’re the sort of outfit that doesn’t confirm things, and she phones someone else.
When a reply to an enquiry doesn’t arrive, the person decides you couldn’t be bothered to answer. You never learn either of those things. What reaches you is a customer who went quiet.
Email doesn’t break loudly. It breaks in silence, and silence looks exactly like someone who changed their mind.
There are two faults that lie underneath this, and they sit at opposite ends of the problem.
The first is authentication, which sounds technical and isn’t. Three short records live in your domain’s settings and do one job: they tell Hotmail, Gmail, Outlook and the rest that mail claiming to come from you genuinely comes from you.
That domain was missing them. The email still went out — it just arrived with nothing to vouch for it, and a receiving mail server treats a message with nothing to vouch for it roughly the way you’d treat a stranger with no ID. Sometimes it lets the message through, sometimes it drops it in spam, and sometimes it quietly holds it back and tells nobody.
I added the records that same morning, and a test message afterwards passed every check that had been failing the day before.
That fix is free, it lives in your domain settings, and it takes about twenty minutes.
The second fault isn’t the owner’s to fix, which is why it has run since May. The automatic emails — confirmations, enquiry replies — go out through a third-party sending service, and that service’s own log showed the messages dying inside its system, on its own internal error, before they ever left for the customer. The pattern was Microsoft: 10 of the 12 were addressed to Hotmail or Outlook.
Nothing at my end could have prevented it. It’s with the provider’s engineers now, and once they’ve fixed it the failed messages can go again. But I only knew to ask because I opened the log and read it.
One of those customers can’t be reached at all, as it turns out. She’d mistyped her own email address when she filled in the form, so nothing anyone sends will ever get to her. She’ll be phoned instead, three days late, which is better than never.
So here’s the check, and it genuinely takes two minutes.
Send an email from your business address to a Gmail account you own. Open it in Gmail on a computer, click the three dots at the top right of the message, and choose Show original. You’ll see three lines near the top: SPF, DKIM, DMARC. You want all three to say PASS. If any of them says fail, none or softfail, your email is going out without ID, and some proportion of it isn’t landing where you think it is.
That’s the half you send by hand. The other half is the automatic mail — the confirmations, the enquiry acknowledgements, the receipts — which almost always goes through a separate service, and that service keeps a log of every message and what became of it. Open it, filter for anything that doesn’t say “delivered”, and read what’s there. It took me a morning to find 12. The log had been sitting there since May.
It’s the same shape as why a website gets visitors but not enquiries — the traffic is real, the failure is quiet, and the number you’re looking at is fine right up until you check the layer underneath it.
It’s why half of service-business enquiries arrive by phone and most tracking setups record none of them, and it’s the whole argument in the dashboard is a decoy: every layer says it’s working, because every layer is only ever reporting on itself.
None of this needs a specialist if your setup is simple. The records are free, the log was already there, and what the job actually needed was somebody to go and look on a morning when nothing appeared to be wrong. That’s the difficulty with a system that fails silently: it never asks to be looked at.
Send yourself that test email — two minutes, and worth doing. Then open the log. That one takes a morning, nobody ever does it, and it’s where the 12 were.
