Today, we’re starting an experiment at Automattic. Engineers, designers and product managers pair up and pick a challenge of their choice and try to fix it in one month.

While I’m not an engineer, I paired up with my friend and colleague Jon Bossenger to address an issue that’s been bugging me for years: Woo mails often go to the spam folder.

Lack of communication leads to fraud claims

Case in point, three weeks ago we ordered a fairly niche product: replacement parts of our kids’ CamelBak bottles. We only found one site that offered it. We paid for it, and after that it was just crickets: no order confirmation, no reply to our request via the contact form. I was about to contact the payment provider to flag the site as fraudulent, but first gave the phone number on the site another go via WhatsApp.

Finally, we got a response. It turns out that the merchant was having an issue with emails not being sent.

Emails are such a key to the ecommerce system, but they are also such a complex thing to configure. I don’t expect the average merchant to know why so many emails end up in spam by default for example.

Our plan

There are three things we’re hoping to do. First, build a log approach as part of Woo so there’s at least a document of what happened on the site-side. Right now, we need to ask a merchant to install a mail logging plugin for that, and then it only logs emails sent after installation. It unnecessarily delays the troubleshooting.

Next, we’d like to build a more active notification system. If an email is configured in the Woo settings but isn’t sent, the merchant should know about it as well as how to fix it.

Finally, we’d like to explore how we can help merchants make a deliberate choice for a reliable delivery service. That last bit will likely be the most difficult part, but we hope to build on top of Automattic’s MailPoet for that.