Migrating from mailcow to Apple

By Darren Nathanael on Wed, Jul 17, 2024

“MooHoo” - Steve Jobs in his grave probably

Introduction

I finally did it, I’m old. Well, not really. Email has been a really rough topic for me; deliverability is key, but sometimes you just can’t guarantee that with a self-hosted mail server. I’ve been a Mailcow admin/user for the past year or so, and sometimes really, really important emails don’t get sent correctly. For example:

An email to bookstore

Plus, there is the cost of running Mailcow: CPU, RAM, storage, network (IP address), and needing to monitor that IP address to make sure it doesn’t get marked as spam or fall into a blacklist somewhere just because some idiotic person on the same /24 network abuses the hell out of it.

And if you’re wondering about the cost savings, it totals around $48 per month down to $0.93 per month. That’s a lot of money and headaches saved.

My current iCloud+ Plan

The tools that I used

Well, Mailcow push sync sucks, to put it bluntly. Moving manually via drag and drop in Thunderbird is also not an option with 6GB of email data accumulated over my lifetime.

So what gives? Well, I found this free tool that has been around longer than I have: Imapsync.

Copy/synchronize a Mailbox to another, without duplicates! Buying gives me money and an invoice to you or your company.” - Imapsync Online

Well, thank you for the free tool! We’re now off to the races! Migrating 6GB worth of email only took one week. Holy cow [get it… 🙂], that was painful.

iCloud mail setup

Now that I have my data migrated, setting up the addressing and rules is literally plug and play.

My iCloud+ Mail rules

Since I already use Cloudflare and Apple has integration with it, all it took was two clicks to add the domain, and it automatically set up DKIM, SPF, and all the goodies on my Cloudflare DNS. Or if you’re not using Cloudflare, you could just follow this handy dandy guide by Apple themselves: Apple Support Guide.

iCloud+ features

My experience switching to Apple iCloud+

No more delivery failures. No headache, just plain old it works.

Mail tester results sending mail from iCloud+ custom domain

https://www.mail-tester.com/test-z5evsk07s&reloaded=2

Honestly, it was such a relief for me—zero maintenance for email now. No need for any stupid monitoring.

Photo by Laurenz Heymann on Unsplash