Reverted my domain back to Microsoft 365.
Wanted to test it out to see how it was. Especially considering that it's "free" as I have Apple One. Was pretty much as I expected. Easy setup and everything is rather straightforward and seamless as long as you are using Apple hardware and software.
But once you toss Windows devices into the mix it becomes a mess. Using the iCloud for Windows software does not take your custom domain into consideration whatsoever. It's early, and it's BETA so this behaviour might improve but as for right now the only way to get my custom domain working in Outlook 2021/365 on Windows is by having iCloud for Windows installed so it gives me my
@me.com e-mail, calendar and contacts. Then I have to configure my custom domain as a IMAP account manually and change the username from my custom domain into my
@me.com account for it to be able to authenticate.
This results in the e-mail existing twice, one for
@me.com and one for my custom domain so I have to fiddle with manual rules for notifications so I don't get each and every notification twice.
Why do I have to do it like this? Because Apple doesn't provide any details on how to configure calendar or contacts manually. All they provide is IMAP and SMTP details. This gives me e-mail, but no calendar or contacts. Only way for me to get the calendar and contacts going is by using iCloud for Windows with it's automated process but that will only give me my
@me.com account without any capability of sending e-mails using my custom domain. So I have to do this hack combining both options with all the drawbacks this entails.
iCloud doesn't mix with Outlook very well to begin with, even with the iCloud for Windows plugin. Apple is using the Sent Messages and Deleted Messages folder by default which is not showing in Outlook. Outlook is using Sent Items and Deleted Items by default. The result is having Sent and Deleted Messages being spread over different folders, and the Sent Messages and Deleted Messages aren't showing in Outlook at all so all e-mails going into these folders by default when using Apple Mail on iOS, iPadOS and macOS is not viewable in Outlook. I had to manually re-configure on beta.icloud.com and in Apple Mail so it uses Sent Items and Deleted Items folders created by Outlook as defaults instead.
Notifications are worse with iCloud which is relying on IMAP compared to Microsoft 365 / Hosted Exchange that is using Exchange Active Sync. Notifications of new e-mails is not arriving at the same time on my devices. My iPhone might receive the notification several seconds or even minutes before my mac or iPad or the other way around. When deleting a mail or marking a mail as read on one device my other devices might not notice until several minutes later. Notifications on iOS and iPadOS is not clearing based on whether I have read the notification and even marked the mail as read on another device. Exchange Active Sync is far better at handling all of this stuff.