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How to Sync Apple iCloud and Outlook Calendars

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Table of Contents

Introduction

Trying to juggle Outlook and iCloud calendars can make it difficult to schedule meetings and personal events without having one conflict with the other. This article is going to show you how to sync Apple iCloud and Outlook calendars so you, your colleagues, and your family see your accurate availability across both calendars.

Read this article to learn:

  • The problem that arises from having multiple calendars which are not synced. (It is pretty confusing so it helps to lay it out explicitly.)
  • Some things that DON’T work for syncing Outlook and iCloud calendars (even though many Bing and Google searches suggest they do!)
  • How to use CalendarBridge to automatically, two-way sync iCloud and Outlook calendars.

The problem with having both Outlook and Apple iCloud calendars

Consider Adele. At work she has an Outlook account associated with her work email address adele@contoso.com. She also has an iCloud calendar associated with adelev2024@iCloud.com and she shares that calendar with her family. The problem is

  • when her Contoso coworkers check her availability in Outlook, it doesn’t consider her iCloud calendar.
  • when her family members check her iCloud Calendar, it doesn’t consider her Outlook calendar.
Adele's outlook calendar
Adele's Outlook calendar
Adele's iCloud calendar
Adele's iCloud calendar
Outlook scheduling assistant
Adele's availability in Outlook does not consider Adele's iCloud calendar

So if you have been getting double booked by coworkers who can’t see all your calendars, or if your family members are just annoyed at always having to email you to check your availability, the rest of this article shows you a couple ways to sync your iCloud and Outlook calendars so that coworkers see your correct availability.

Connecting your iCloud account to Outlook on your Device

If you just need to see your iCloud calendar in Outlook for Windows, Outlook for Mac, Outlook for iOS, or Outlook for Android, you can simply add your iCloud account to those apps.  Here’s how to do that.

The benefit of adding an iCloud account to an installed version of Outlook are:

  • you can see and manage your iCloud account from within Outlook
  • You can overlay your iCloud calendar and Outlook calendar in a single view

The limitations of adding your iCloud account to Outlook on your device:

  • your iCloud account is only on that particular device; you need your iCloud account separately to each device you want it on
  • you cannot add an iCloud account to Outlook on the Web (whereas you can add personal Microsoft accounts and Google accounts to Outlook on the Web)
  • adding your iCloud account to Outlook will not block off the availability that your coworkers see when checking your calendar in outlook
  • adding your iCloud account to Outlook will not allow your coworkers to see your iCloud availability

Adding your iCloud calendar to Outlook with "Add calendar from URL" and "import"

Common advice for how to sync your iCloud calendar to Outlook Calendar is to use Outlook’s “Add calendar from URL” or “Import” features.  Our article on How to Share an Outlook Calendar goes into detail what these features are and when they can be useful, but for purposes of this article it suffices to say that neither of these features will keep your Outlook and Apple iCloud calendars in sync. Here is a short summary of what those features do and their intended use.

Outlook Calendar “Subscribe from Web” or “Add calendar from URL” 

This feature is named differently in different versions of Outlook, but in all case it acts the same. When you “subscribe from web” or “add calendar from URL” in Outlook, Outlook will add it as a secondary calendar, and “updates can take more than 24 hours.” Because it is a separate calendar from your primary Outlook calendar, availability on the subscribed calendar will not affect your availability that coworkers see in Outlook. Also, because it is only updated every 24 to 48 hours, it is not useful for viewing a calendar that changes regularly. Rather, subscribe from web is really intended for calendars that don’t change much, such as holidays, sports team schedules, etc.

Outlook “Import” or “Upload from file” 

The “Upload from file” function in Outlook is a one-time copy of events to your Outlook calendar. There is no ongoing connection to the imported calendar. Thus, “import” differs from “Subscribe from web” in two ways: (1) Outlook will not periodically check the imported calendar for updates; (2) you can import events into your primary calendar whereas “Subscribe from web” adds a secondary calendar to Outlook .

The "subscribe from web" and "upload from file" features of Outlook Calendar do not sync availability, and are generally too slow to be reliable

Adding your Outlook calendar to iCloud with "Add subscription calendar"

Please note that you should only use Apple Calendar’s “Add subscription calendar” if for some reason you cannot directly add your Microsoft account to your Mac or iOS device.” Directly adding your Microsoft account (i.e., going to “add account” and then logging into your Microsoft account) will give you full ability to manage your Outlook calendar from your Mac or iOS device, whereas “Add subscription calendar” only lets you see a read-only copy.

To subscribe to your Outlook Calendar from Apple Calendar, first you need to get the .ics URL of your Outlook calendar  (our article How to share an Outlook calendar covers that). Then, follow these directions: Using iCloud calendar subscriptions.

Once that’s done, you will be able to see your Outlook calendar from within the Apple Calendar app. The subscribed calendar will update each time you close and open the Apple Calendar app.

If other Apple Calendar users need to see your Google calendar, you will have to provide them the .ics link to your Outlook calendar so that they can subscribe to it.

Finally — and most-importantly for this discussion — subscribed calendars in Apple Calendar are separate from your existing iCloud calendars. This means that subscribed calendars won’t affect your availability on your iCloud calendars, and your iCloud calendars will not affect your availability on subscribed calendars. So if your goal is to block off time on one calendar based on the other, Apple Calendar’s “Add subscription calendar” is not the solution.

If you need to block time on your Outlook calendar based on your iCloud calendar, or visa versa, Apple Calendar's "Add subscription calendar" is not the solution.

Outlook's "share calendar" features

Outlook has the feature to “share” your calendar with others. The various sharing options are a pretty complicated, but for our purposes here it is enough to point out these limitations of “sharing” your Outlook calendar:

  • To share a between Outlook and iCloud, the calendar needs to be made public.
  • Making a calendar public and sharing it has the same limitations as the “Subscribe from web” feature discussed above — events are added as a separate calendar and do not block off one calendar based on the other.
  • Many companies block the ability to share your Outlook calendar with people outside your organization.

Using Outlook's "share calendar" will not affect availability on your existing iCloud calendars.

How to two-way sync Apple iCloud and Microsoft Outlook calendars using CalendarBridge

If you need consistent availability between existing Outlook and iCloud calendars, CalendarBridge is the best calendar syncing service to do it.

Some example use cases of CalendarBridge: 

  • sync to and from Google calendars
  • sync to and from personal Microsoft calendars (@outlook.com, @hotmail.com. @live.com, and @msn.com addresses)
  • two-way sync between Google, Outlook, and iCloud calendars
  • sync up to 6 calendars in both directions or up to 36 calendars in one direction.

1. Create a CalendarBridge account (7-day free trial)

2. Connect your iCloud and Outlook accounts

Follow these instructions on Connecting your Calendar Accounts to CalendarBridge. CalendarBridge connects to Google via OAuth (“login with Google”) and connects to iCloud with an app-specific password so that we never see your Apple or Google credentials and you can revoke our access at anytime from your Google or iCloud account settings.

3. Configure which calendar events to sync and how to sync them

Each sync connection defines:

  • a source calendar from which to copy events/availability 
  • a destination calendar to which to copy the events/availability
  • privacy settings to control which specific fields/information you want to sync. You can sync all details, no details (just create “busy” slots on the destination calendar), or somewhere in between. 
  • filters to exclude certain events from syncing. 

4. View your synced calendars

CalendarBridge does not store your calendars anywhere. We simply copy events directly between your iCloud and Google calendars. This means that you continue to view your calendars in whichever calendar app you already use — Google calendar, Outlook, the iPhone calendar app . . . wherever!

Why sync your Apple iCloud and Microsoft Outlook Calendars with CalendarBridge?

  1. Calendar updates sync in seconds. Unlike import, subscribe, and share features built into Apple Calendar and Outlook, CalendarBridge provides fast, automatic calendar syncing direclty between your existing calendars so you, your colleagues, and your family can rely on the availability shown in your calendar.
  2. Privacy controls. With CalendarBridge you can sync as little or as much detail between calendars as you want. If you want to be able to see all the details of your events in both calendars, you can do that.  If you want to make sure even I.T. administrators can’t see the details of your synced events, you can do that too.
  3. Simple setup. Setting up CalendarBridge to sync your iCloud and Google Calendars takes just a few minutes. There is nothing to configure or install on any of your devices.