Sending Emails Is Hard

One thing I've had to learn after leaving Substack is how to properly send mass emails. Spoiler alert: it's not easy. And, starting on Thursday, Google and Yahoo are making it a little harder.

Ok, let me walk back here a second. In actuality, sending emails is really easy. You just hit send, and it goes. However, making sure the email lands in someone's inbox and not the "promotions" or spam box is the tricky part.

On Thursday, Google and Yahoo will start enforcing DKIM, DMARC, and SPF DNS records. These settings are added to your domain, and then email servers check when they get a mass email. As long as everything's set correctly, the server thinks the email is on the up and up.

Let's drop an example here. I send my newsletter using Mailgun. So, I set the DNS records to allow Mailgun to send emails on behalf of justincox.com. This way, when the email arrives in your account, the server (i.e., Google) verifies that Mailgun is authorized to send the email. Since that's the case, the email will likely end up in your inbox.

Of course, there are likely a lot more technical details involved, but they aren't important. What is important is that the world's biggest email providers will start enforcing these settings on February 1.

These rules are great because they should help curb spam. Email senders who make it look like their emails come from domains other than they actually do will get caught. After all, Apple won't allow some random Russian email account to send on its behalf.

What's not great about these rules is they aren't easy to set up. Two weeks ago I took the weekend and applied all the rules. I used tools like Cloudflare and MX Toolbox to test the settings before the sending all checked out.

Any tool that you use to send emails should provide you with the DKIM, DMARC, and SPF records to apply to your domain's DNS. However, the DNS settings aren't the only things that determine if your email is considered spam or not. There are multiple other factors, such as:

• How many people report the email as spam.
• How many email addresses you send to that bounce.
• How many people respond to or engage with the email.

If you manage your website and email sending, these are all critical things to consider. But the silver lining here is spam should slow down. Hopefully. Maybe...

Regardless of whether the tools work to reduce spam or not, they make me feel better about sending mass emails. I only want to send emails to people who want to read them. It makes for a much better experience for me, the writer, and you, the reader. After all, no one wants a bunch of emails they aren't interested in.

The Purge 2: Unsubscription Day

Speaking of only sending emails to people who want to receive them, I conducted another subscriber purge over the weekend.

This time, I sent a warning email, which felt like a smarter thing to do. In the email, I let people know they were about to be purged because Ghost hadn't recorded any email interaction from their account.

Here's the thing, I don't really like tracking metrics. I don't want to be tracked and I don't really want to track you. But, I keep a few Ghost and Mailgun metrics in place to know who opens emails and when emails bounce. This way, I can keep a cleaner list.

There are, though, a lot of ways to block email tracking. Apple has it baked right into its operating systems, and I encourage you to use it. The downside is that I won't know when you open an email, and you might end up on the Purge List.

Thankfully, there are two easy ways to stay off the purge list:

1. Upgrade your membership to a paying member. Those on the newly renamed Team Justin never have to worry about the Purge List.
2. Click the 👍🏻 at the bottom of an email every now and then. Ghost puts a unique code in the link, allowing me to filter users who leave feedback.

I really hope you enjoy reading my writing, but I completely understand if you don't want another email.

Feedback Wanted: Should the site go into lockdown?

Speaking of email, Ghost has a feature to prevent people who aren't on the email list from reading content on the website. Right now, my entire website is open to anyone. However, after reading 404 Media's latest report, I'm having second thoughts.

The entire article is worth a read, but I'm particularly concerned with the section titled "AI Spam Is Eating the Internet, Stealing Our Work, and Destroying Discoverability."

Sam’s investigation into the inclusion of child sexual abuse material in the LAION large language model, a hugely important and sensitive story that we ultimately worked on over the course of nearly a year before we even launched, consulted with a lawyer on, and spoke to many experts for, quickly became an article called “They Delete A Database To Train AI Generative Images To Contain Child Sexual Abuse Material” on a website called “Nation World News.”

The article provides multiple other examples where their articles, full of in-depth and highly researched journalism, almost immediately appeared on AI-generated spam sites. As a result, 404 Media is putting all of its articles behind Ghost's subscription wall.

I'm now considering the same. While I want my writing to be available to everyone, I've dealt with plagiarizers and content-scrapers in the past. It really sucks, and there is, unfortunately, little recourse when it happens.

I'm considering putting all stories on my site behind the subscription wall, requiring people to log in to read online. Doing so would require setting up an account on the site (if you're reading this in your email box, you already have one). If you're purged from the email list or you sign up without subscribing, you can still read online while logged in.

But before I go all in, I'm curious about your thoughts. Please hit reply and let me know if you think this is a good idea or a restrictive barrier. After all, I don't want to make my writing harder for humans to read, but I do want to make it difficult for malicious actors to steal.