Hey there,
I'm making a trip later this month and a few days ago I realised I couldn't find my hotel booking confirmation anywhere.
I searched my inbox, checked spam, tried searching by the hotel name, the booking platform, every variation I could think of. Nothing. So I ended up calling customer support, sitting on hold for half an hour, and eventually getting someone to resend it manually.
I don't like phoning people at the best of times, so I can tell you now I probably won't book through that platform again. That one missing email wasted my time and made the whole experience feel unreliable.
If you think this kind of story sounds familiar, it's because I write about email going wrong fairly regularly. And (hand on heart) I don't make these stories up. once you start paying attention to how email actually works, you start noticing just how much has to go right for a message to land where it should, when it should.
And when a customer is the one sitting on hold because your site's order confirmation or password reset never showed up, it's your reputation taking the hit, not the email provider's.
When that happens, the first thing to check is your email log. If it shows the email sent successfully, you know it left your site. But that's also where most people get stuck, because once the log says "sent," there's not much else WordPress can tell you about where it went.
The reasons an email can go missing after that point are pretty varied.
It might have bounced, in which case your SMTP service dashboard will usually tell you why. It could be an authentication issue: SPF, DKIM, or DMARC either missing or misconfigured, which causes receiving servers to reject or filter the email. It might be a sender reputation problem, where your domain or IP has ended up on a blacklist. There are also a handful of WordPress-specific causes, like your From address not matching your authenticated domain, or a plugin conflict.
And sometimes it's just a temporary outage with your email service, which thinking about it, might well be what happened with my hotel confirmation. In those cases there's nothing wrong with your setup at all, but a backup mailer would have caught it automatically and sent it through a second provider while the first one was down.
I put together a full troubleshooting guide that walks through all of these, including how to read bounce codes, how to check your authentication records, and how to tell if reputation is the issue. If you've ever had a customer tell you they never got an email you're certain was sent, it's worth bookmarking.
Until next time,
Rachel
Product Educator, WP Mail SMTP
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