Why is calendar not syncing on Mac?

David Farren has a macOS calendar issue. He has two Macs, an iPhone, and an iPad mini, and after using a third-party calendar app for a year, he decided to switch back to Apple’s native Calendar apps in iOS and macOS.

On one Mac and his iOS devices, all went tickety-boo: the entries he’d made in the third-party app for iCloud calendars all appropriately appeared. But his second Mac is throwing up errors.

When I try to prompt it to sync with iCloud, it just brings up a message saying, “Cannot connect to cal.me.com.”

All his preferences are the same on both Macs, and all other iCloud-based sync items properly keep up to date. David’s not alone. It’s easy to find several—but not, say, thousands of—other people having this problem across several years. Apple offers a large array of generic advice, but doesn’t address this situation. (It also has a page of in-depth calendar troubleshooting linked from that FAQ, but strangely it’s noted as no longer being maintained.)

No one has a great solution for this, but you can try one bit of troubleshooting and one attempt at eliminating other variables.

First, turn Calendar off and on in the iCloud system preference pane. In some versions of OS X/macOS you might be prompted about saving calendar information as a local copy. Choose Delete if so. If that solves the problem, hurray!

If that doesn’t work, create a new account in macOS for testing, use your iCloud account information, and see if calendar information syncs. If so, it’s not your Mac, network configuration, or other problems. It’s just your particular macOS account, which means there’s an errant file, cache, or misconfiguration in that account’s set of files.

If you can’t get calendar syncing to work in a fresh account or you can but can’t ultimately fix it in your main account, a last resort is to reinstall macOS without deleting your current system. While that seems extreme, I’ve had to carry this out several times for various reasons recently, and the process of reinstallation has been much smoother than in years past. Make sure to make a full clone or Time Machine copy before attempting a reinstall.

Ask Mac 911

We’ve compiled a list of the questions we get asked most frequently along with answers and links to columns: read our super FAQ to see if your question is covered. If not, we’re always looking for new problems to solve! Email yours to [email protected] including screen captures as appropriate. Mac 911 can’t reply to—nor publish an answer to—every question, and we don’t provide direct troubleshooting advice.

Author: Glenn Fleishman, Senior Contributor

Glenn Fleishman’s most recent books include Take Control of iOS and iPadOS Privacy and Security, Take Control of Calendar and Reminders, and Take Control of Securing Your Mac. In his spare time, he writes about printing and type history. He’s a senior contributor to Macworld, where he writes Mac 911.

Currently, Outlook for Mac doesn't support the CalDAV or CardDAV Internet standards. This means Outlook for Mac does not sync your iCloud Calendar or contacts when you add your iCloud email account. That being said, there is a way to sync your iCloud calendar with Outlook for Mac—you can subscribe to your iCloud calendar to Outlook on the web (Outlook Web Access), and once you do that, the subscribed iCloud calendar automatically syncs with Outlook for Mac.

1. Open a browser window and sign in to your iCloud account.

2. In iCloud, click Calendar.

3. Click the Share Calendar icon next to the calendar you want to configure in Outlook, and make sure Public Calendar is enabled.

   

   Note: If Public Calendar is enabled, you should see the Uniform Resource Locator (URL) of the calendar.

   

4. Click Copy Link.

5. In another browser window, sign in to Outlook on the web.

6. At the bottom of the navigation pane, select Calendar.

   

7. On the toolbar, select Add calendar > From internet.

   

8. In the Calendar subscription dialog box, paste the link that you copied in step 4. Also, enter a unique name for the calendar such as "iCloud work Calendar", and click Save.

   You should see the iCloud calendar listed under Other calendars in Outlook on the web.

   

   When you have the same account added on Outlook for Mac, this subscribed calendar will also appear in Outlook for Mac calendar.

   Note: It may take a few minutes for the iCloud calendar in Outlook on the web to sync with Outlook for Mac. Please remember that you may have to restart Outlook for Mac in order for the synced calendar to appear.

   

Notes: 

• The account signed in to Outlook on the web has to be also added to Outlook for Mac. The account can be your work or school account on Office 365 or Exchange or any Outlook account (such as @outlook.com, @hotmail.com).

  Why isn't my Calendar syncing with my Mac?

  Check your internet connection and try refreshing or updating the calendar again. Also, make sure the calendar hasn't been deleted or moved. To see the calendar's web address, Control-click the calendar's name, then choose Get Info.

  How do I force my Mac Calendar to sync?

  Method 1. (If you're using macOS Mojave or earlier, go to System Preferences, then click iCloud.) Uncheck the box of Calendars, then select Delete from Mac, your iCloud Calendar is turned off. A few minutes later, go to System Preference > iCloud, turn on iCloud Calendar and check if the calendars are synced to iPhone.

  Why is my Calendar no longer syncing?

  Check your device's storage Calendar stops syncing if your device is running out of storage. Open the Settings app on your device (not the "Google Settings" app). Find the Storage section. If you need to clear space, try uninstalling apps you don't use or deleting files or photos from your device.

  How do I get my Mac and iPhone calendars to sync?

  Sync calendars to your device: Select the “Sync calendars onto [device name]” checkbox, then click “All calendars” or “Selected calendars.” If you clicked “Selected calendars,” select the checkboxes of the calendars you want to sync in the Calendars list.