GoDaddy and Microsoft Failed Me. Then Came Claude.

In mid-January of this year, I was catching up with a friend on the phone. He asked me if I received his recent email about a job reference. Oddly, I hadn't. Time to do some digging.

I soon learned that I wasn't special. Untold GoDaddy customers were no longer receiving their business emails. The company was experiencing what would turn out to be yet another multi-day Outlook service outage. Even more infuriating, GoDaddy again didn't deign to alert affected individuals. No messages to their backup email addresses. Nary a text. No automated phone calls. Zilch.

GoDaddy's lack of communication irritated just as much as the technical disruption. Just like Pacino in The Insider, I was pissed off and curious. I enlisted Claude to start investigating alternative email providers. Eventually, I decided to kick the tires on Fastmail (affiliate link). As you'll see in this post, I ultimately came out ahead.

An Early Obstacle

I began my migration by changing my MX records. I then exported my emails from GoDaddy to FastMail. Next up, I downloaded my existing blacklist from my personal GoDaddy quarantine page:

To replicate my previous setup, though, I needed to migrate all my existing Outlook email rules. How hard could that be?

Impossible, because Microsoft prohibits Mac users from taking this action. Can someone say vendor lock-in? Maybe the Redmond behemoth only cares about data sovereignty in Switzerland. Ultimately, my hundreds of email filters remain trapped in Outlook and currently unusable.

My MX records propagated. I was now officially on Fastmail, but all new messages arrived in my inbox—not in their carefully curated folders and subfolders. What's more, I received absurd emails from icky domains and scammers that I had previously blocked through my advanced keyword-based filters in Outlook.

I spent about a week intermittently recreating prior filters as I received a variety of messages. By early February, though, I had figured out Fastmail. Why not start noodling with its advanced features?

I soon began to sense that there might be a better way to attack the problem than playing Whac-A-Mole. I then asked myself the following question:

Was replicating my previous rules-based approach to fighting spam really right way to go?

Perhaps my GoDaddy/Microsoft fiasco actually represented an opportunity to build a more sophisticated mousetrap.

A More Modern Approach to Fighting Spam