Background
I have a Mac client that have one work email (MS365) and one private email.
Since his work is using Outlook and all that MS365 stuff, he now wants to move both of his email accounts and calendar stuff to Outlook.
I am no Outlook user so I couldn’t give any good advise on how to best solve this, but maybe someone here can give any advise?
Solution?
Set up an email in Outlook shouldn’t be that hard, but how about the calendar stuff? Will it still sync with iCloud? How about old calendar events, will that be visible? etc etc.
I don’t know how … but what comes to mind is why not use both. Either setup Outlook to connect to iCloud account, or Apple Mail to connect to MS365 Outlook (assuming it;s that).
On my Apple Mail app, I’m connected to numerous IMAP, Outlook (Exchange), and iCloud Accounts. My wife’s university Outlook app on Mac is connected to Outlook (Exchange) and iCloud.
Or “jump through hoops” to move completely off Mail and iCloud.
It appears that in order to view calendars from other services, Outlook needs to have a URL.
I don’t think iCloud calendars have a publicly-shared link that isn’t read-only. (But I could be wrong.)
The solution might be to switch to using Microsoft’s calendaring engine instead of Apple’s. To make the move, on the Mac export the current calendars into .ics files. Then import them into Outlook and carry on from there. I don’t know how far back an export will go, but I hope it would be everything visible on the Mac.
One thing you should discuss with your client — what about the address book? If he is going all-Outlook, then he should probably move all of his contacts to Outlook as well.
Using two calendar services or two contacts services is a recipe for frustration. I have helped several clients troubleshoot and fix their screwed-up contacts when they had both Outlook/MS365 and iCloud on their devices.
Also, if he has an iPhone, you’re going to need to figure out how to configure it properly so new contacts or calendar entries go to the correct place.
I was able to sync my iCloud calendar with Outlook, but it proved unreliable. Events didn’t always appear. Something I created in Outlook for iOS didn’t always make it to Outlook for MacOS… but did appear in Apple Calendar!
I realize this probably isn’t helpful. I’m going to jump on the why not both wagon.
Calendar sync is problematic, but Microsoft provides instructions for adding iCloud Mail to Outlook. Given Windows users have to use iCloud for Windows for to get iCloud Calendars to show up in Outlook, Apple probably has systems in place to keep Mac users from using Outlook for calendaring.
The Outlook app for Mac is not very good and probably would create more headaches for you. Last time I checked, it doesn’t offer feature parity. Outlook on the web is a better option and you get all the options.
This works so-so. I have added a Google Calendar to MS Outlook 365 and yes, it imports it, but the refresh time is not that good.
The best solution I’ve found for calendaring is to use the native macOS integrations with Google and MS Exchange, then all my events appear in Calendar.
