Originally Posted by
Sabre Wulf I switched from Outlook.com to iCloud mail a month ago. I have found it to be great for my needs, although admittedly my needs are not great. I like that it is part of the ecosystem, along with the other cloud services and Apple Music.
Outlook.com is now on the Exchange infrastructure. They're all Hosted Exchange Accounts, pretty much (except those accounts which haven't been migrated - all new Accounts are created there by default, since the old infrastructure is being quickly phased out). If you have access to Microsoft Outlook (even the 2011 version), then there is very little reason to bother with iCloud. Microsoft Outlook on Mobile is as good as any other, so that's not really a consideration...
This is especially true if you use a mix of platforms across different form factors. Apple's UX is already rather lackluster on their own platforms, IMO. Once you go beyond that, it quickly devolves into terrible.
Issues I've had with iCloud Mail:
1. The lackluster Web Client. Sluggish and Slow. Outlook is incredibly far ahead of Apple there, and I find Microsoft's Web Services for PIM to be the cleanest that I've ever used - especially the new version of Outlook. Very few distractions, well designed, and incredibly performant (it's basically Outlook Web Access for consumers).
2. The fact that main things you can do across Apple's own platforms are client-side settings only. This means that when you want something "to be a certain way" on your Mac, it may not actually be mirrored on your iPhone. This is not the case with Outlook on Exchange, since everything is server-side.
3. Having to jump across 4+ Apps for PIM Tasks (Mail, Calendar, Contacts, Notes, etc.)
4. On Mobile, the iCloud Mail Synchronization speed is absolutely horrific with iCloud. It's incredibly slow. It's also very inconsistent. Hundreds of times I've "cleared my trash" or deleted multiple emails only to see them reappear after the Sync was "finished." This literally never happens with Exchange.
5. The way Microsoft Outlook integrates Cloud Storage (OneDrive, etc.) on Mobile is fantastic. Apple still hasn't really gotten iCloud baked into their OS well. As an aside, I was quite astounded that I couldn't save a PDF I was viewing on iOS to my iCloud Drive...
6. Spam Calendar Event Invites. I had never experienced such a thing until recently... On iCloud.
7. I find Microsoft Outlook 2016 to perform much better than Apple Mail, while loading just as fast and incorporating the job of 3.5+ Apple Stock Apps into one.
8. Exchange Categories, etc. are significantly ahead of iCloud. For people who like to be organized, iCloud actually isn't that good. You're much better off with Gmail (though you lose the great client experience and synchronization flexibility) or Outlook.
9. Because Outlook is one application, it can do things more efficiently when it comes to working across different sections of PIM (i.e. selecting an email message and clicking "Meeting" to create an appointment referencing that email with almost no work).
10. Being saddled with IMAP and Cal/CardDAV for Synchronization with iCloud. And to get any decent Synchronization on Windows, you need Microsoft Outlook and an incredibly heavy plug-in installation... If you have Outlook, then why even bother with iCloud at all, especially if you ALSO use Windows.
Still, I've used it since it was convenient enough given the poor support Outlook had (in the past) for Outlook.com. This is no longer the case. It's amazing, now. On the Web, on Windows, on macOS, on Mobile... Hell, even on Linux if you use Evolution (I believe it has Exchange support) or any platform which supports Exchange or EAS.