What to do when a calendar isn’t syncing to your Mac

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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.

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