Can my iPhone or Mac synchronize with other types of calendars?

We’re occasionally asked if an iPhone or Mac email address with us can “sync” with an iCloud or Microsoft Outlook calendar.

These have two different answers:

Syncing between a Mac and iPhone with iCloud

Old versions of the Mac and iPhone mail apps used to show a “calendar” checkbox option when adding an IMAP email address. This was because they didn’t have a way to directly synchronize calendars between devices, so Apple used invisible email messages behind the scenes as a way to do it.

Calendar synchronization on the Mac and iPhone is now handled directly by iCloud, though, and email is no longer involved at all. Modern Mac and iPhone mail programs don’t show the “calendar” checkbox for email accounts because it’s no longer needed. Instead, you can set up calendar syncing within iCloud.

(People occasionally ask us why Gmail or Microsoft Exchange email addresses still show a “calendar” option when you add them. That’s because Google and Microsoft provide unrelated, extra calendar services in addition to their mail service, and the option enables those extra calendar services. The email address is used only as a username for your calendar account with them, though; the calendar is not literally part of the email service.)

Syncing Microsoft Outlook calendars with Apple programs or devices

The Microsoft Outlook software program can create calendars as well as handling mail. It allows you to schedule events and invite people to attend, and then keeps track of all those details.

We’re occasionally asked if it’s possible to keep the Outlook calendar in sync with the Apple iCloud calendar built into the Mac and iPhone (described above). Unfortunately, there's no built-in way to do this, as confirmed on this Microsoft page, which says “No. The calendar in Outlook for Mac doesn’t sync with any of your iOS devices”.

There are some third-party tools that claim to enable this, but we haven’t tested them ourselves.

The “proper” way to synchronize Outlook and Mac calendars would be to connect your Apple calendar to what’s called a Microsoft Exchange server. An Exchange server can act as the “middleman” that stores your calendar data, and both the Outlook program and the Apple calendar program can “talk to” that kind of server. Unfortunately, we don’t offer Exchange Servers, so you’d need to use a different company to be able to do this.

Companies that offer Exchange servers usually bundle both email and calendar options in one package. An Internet search for “Exchange server” should show several possibilities, including Microsoft’s own Office 365 service. If you want, it’s possible to use one of these companies for your email and calendars while keeping your website with our company.