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1.3. Sync with iCloud account

Apple requires third-party apps (like Calendars) to use app-specific passwords with iCloud accounts. An app-specific password is a single-use password you generate on the Apple ID webpage and paste into the password field while adding your account to Calendars.

Step 1. Enable two-factor authentication

To generate an app-specific password, make sure you have two-factor authentication enabled.

Note: Some Apple IDs created in iOS 10.3 or macOS 10.12.4 and later versions are protected with two-factor authentication by default. 

1. Open System Preferences on your Mac.
2. Go to iCloud > Account Details.
3. Click Security at the top.
4. Make sure two-factor authentication is on. Otherwise, click Turn On Two-Factor Authentication.

Step 2. Generate the app-specific password and add the account

1. Open the Apple ID webpage. Sign in as usual.
2. In the Security section, click Generate Password.
3. Enter the password label, e.g., “Calendars,” and click Create.
4. Copy this password.
5. Return to Calendars and try adding your account again using the generated password.

Please make sure that while adding your account to Calendars, you use your iCloud email address, not an iCloud alias. You can check your email address in Mail on iCloud.com (click on the Settings icon at the bottom right > Preferences > Accounts).

Note: App-specific passwords work only for the iCloud email address with the @icloud.com, @me.com, or @mac.com domain name. This address can differ from your Apple ID email address (e.g., your Apple ID may be linked to Gmail, Outlook, or other emails). You can see the iCloud email address you need in the “Reachable At”/“Contactable At” section on the Apple ID webpage. 

Troubleshooting

If, after using the app-specific password, your account still can't be added, please check the following:

1. The Internet connection on your device is stable. With poor connection, Calendars might not be able to add your account.
2. VPN is not enabled on your device. If you use a VPN, we can’t guarantee Calendars will work properly. The quality of the performance via VPN solely relies on the servers of the VPN network. For this reason, we recommend you turn the VPN off.
3. There aren't issues with iCloud accounts on Apple's side. You can check this info on Apple's System Status page.

If the steps above didn't help, you can try connecting your account through local calendars:

1. Add the needed calendar to the local Calendars app first.
2. Open Calendars by Reaadle.
3. Press ⌘, > Local Calendars. Alternatively, click Calendars in the Menu Bar at the top, then select Settings > Local Calendars.
4. Enable the display Local Calendars toggle and choose the accounts to display. That’s it!

Note: If you already have some of the accounts added to Calendars by Readdle and don’t want them to be added twice to the app, disable them in the Local Calendars section of Settings (⌘,). Disabled accounts will still be available for other apps and systems.