Nearly two years ago, I wrote about my experience switching my personal email to iCloud Mail with their custom domain feature. My experience was mixed, and I've since received numerous comments asking if I'm using iCloud Mail, and how things are going.
The headline is, I've found myself returning to iCloud Mail each time I leave. During this time, I switched to Microsoft 365 for six months and dabbled with Fastmail again, but ultimately returned to iCloud Mail using my custom domain. While it's clear iCloud Mail is far from perfect, and other services may be more capable, something has clearly kept me here.
Over the past two years, outside of iCloud Mail, I've spent the majority of the time on Microsoft 365's Exchange offering. The price is approachable, it's infinitely customizable, and search, spam, and the web app are all market leading.
I switched from iCloud Mail after a long flight where the mediocre Wi-Fi had me struggling to load the iCloud web app on my work laptop. I was also experiencing an iCloud Keychain issue that had me spending far too much time with Apple Support. I began to worry about how critical my Apple Account had become, and decided it was time to diversify.
Setting up Microsoft 365 Exchange is not what I would call “easy”. There are endless admin panels for all the different services and features. It took a good weekend of tweaking and tuning to get everything configured the way I wanted it, complete with an account for my wife and mailboxes for my young kids. The service is clearly not made for families or small organizations, and I was ok with that.
I thoroughly enjoy Outlook from a browser and on a Mac. It's fast, with great search and good filtering. Deliverability is top-notch, and the plethora of add-on services are a nice bonus. I'd moved some of my files to OneDrive, used Teams for personal meetings, and even found the to-do app decent enough. Cracks started to show when I tried to set up a family calendar and a shared folder in OneDrive, only to have to configure a SharePoint site. The fragmented, complicated experience ensured I'd never successfully get my family onboard.
In June of this year, I began to get restless again. The Focus Inbox, one of the features I initially liked with Outlook, was broken, spam filtering seemed to be degrading, and I needed a separate subscription if I wanted a phishing solution that didn't really work. I, again, decided to revisit iCloud Mail.
In the two years since launch, the web interface has received a face lift with proper drag-and-drop, nested conversations, a better home screen, and more. It's a bit faster, though nowhere near the others. I've also come to appreciate the rather aggressive message filtering, which requires a sender to properly configure their SPF records for a message to get through. (Have you ever received a spam message from your email address, with someone claiming to have hacked your account?)
Beyond the improvements to the web, Apple added BIMI support to verify senders from large organizations. This works across the web, mobile, and desktops and is a great way to fight phishing attempts.
One thing I truly appreciate is using iCloud for Mail, Contacts, and Calendar. Syncing multiple contact accounts with Apple devices, especially when those accounts have similar contacts within, causes all sorts of strange issues. My family has also come to depend on the iCloud Family Calendar; something that Microsoft 365 doesn't do well. Using another email provider meant fragmenting these three interconnected services.
Finally, the value of the service really can't be overstated. If you subscribe to any paid iCloud plan, you can use up to five unique domains, and each family member can have up to three email addresses per-domain. This ends up making iCloud Mail a fraction of the price of every other service out there, especially when including family members.
To wrap, while I've wandered quite a bit over the last two years, something continues to draw me back to iCloud Mail. With the improvements in mind, and having recently explored the viable alternatives, I'm not looking to change again anytime soon. iCloud Mail is far from perfect, but for personal use with a family, it's truly hard to beat.