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Connect Apple iCloud Calendar

Using CalDAV with App-Specific Password

Important: App-Specific Password Required

Apple requires an App-Specific Password for third-party apps when you have Two-Factor Authentication enabled (which is required for all Apple accounts).

Don't worry! This guide will walk you through generating one. It takes about 5 minutes.

Prerequisites

Before you begin, make sure you have:

An iCloud account (Apple ID) with calendars
Two-Factor Authentication enabled (enabled by default for all accounts)
Access to appleid.apple.com to generate an app-specific password

Step-by-Step Guide

This guide has 2 parts:

Part A: Generate an App-Specific Password from Apple (5 minutes)
Part B: Connect your iCloud calendar in SyncMyDay (2 minutes)

Part A: Generate App-Specific Password

Go to Apple ID Settings

Open your browser and go to appleid.apple.com

Authenticate with Two-Factor

Apple will send a verification code to your trusted devices (iPhone, iPad, Mac). Enter the 6-digit code when prompted.

Enter the 6-digit verification code from your device

Navigate to Security Section

Once logged in, find and click on the "Sign-In and Security" section.

Apple ID account page with Sign-In and Security section

Click on "Sign-In and Security" section

Click "App-Specific Passwords"

In the Security section, scroll down until you find "App-Specific Passwords" and click on it.

Security settings with App-Specific Passwords option

Find and click on "App-Specific Passwords"

Generate New Password

Click the "Generate an app-specific password" button (or the + icon).

When prompted for a name, enter something descriptive like:

SyncMyDay
SyncMyDay Calendar Sync

Tip: The name helps you remember what this password is for, especially if you need to revoke it later.

Dialog for entering app-specific password name

Enter a name like "SyncMyDay"

Copy the Password

Apple will generate a password that looks like this: abcd-efgh-ijkl-mnop

⚠️ IMPORTANT: Copy this password NOW!

Apple will only show this password once. If you lose it, you'll need to generate a new one. Copy it to your clipboard or paste it directly into SyncMyDay in the next step.

Generated app-specific password displayed

Copy the generated password - it will only be shown once!

Part B: Connect in SyncMyDay

Go to Calendar Connections

Return to SyncMyDay and navigate to Calendars in the menu, or go directly to the Calendar Connections page.

Go to the Calendar Connections page

Click "Connect Apple iCloud"

Find and click the Apple iCloud button with the Apple logo.

Calendar providers with Apple iCloud option

Click the "Apple / CalDAV" button

Enter Your Credentials

Fill in the connection form:

Email: Your full Apple ID email (e.g., your.email@icloud.com)
Password: Paste the app-specific password you copied from Apple (including the dashes, or without—both work)

Use the App-Specific Password

Do NOT use your regular Apple ID password. Use the app-specific password you just generated. Your regular password won't work.

iCloud connection form with email and password fields

Enter your Apple ID email and app-specific password

Select Calendars

After connecting, SyncMyDay will fetch your iCloud calendars. Select which ones you want to sync.

Common iCloud calendars include:

Home - Your default personal calendar
Work - If you've created a work calendar
Family - Shared family calendar
Any custom calendars you've created

Calendar selection with iCloud calendars

Select which calendars you want to synchronize

All Done!

Your Apple iCloud calendar is now connected! You'll see it in your calendar connections list.

✅ What's Next?

Your iCloud calendar is ready to use in sync rules
Events will sync every 15 minutes (CalDAV limitation)
You can now create sync rules to keep calendars in sync

Note: iCloud uses CalDAV protocol, which doesn't support real-time webhooks. We poll for changes every 15 minutes to stay up-to-date.

Your iCloud calendar is successfully connected and active

Troubleshooting

"Authentication failed" or "Invalid credentials"

Common causes:

Used your regular Apple ID password instead of app-specific password
Typo in email address or password
App-specific password was revoked

Solution:

Double-check you're using the app-specific password, not your regular password
Generate a new app-specific password and try again
Make sure your email is correct (include @icloud.com or @me.com)

I don't see "App-Specific Passwords" option

This usually means Two-Factor Authentication isn't enabled on your account.

Solution:

Go to Apple ID settings at appleid.apple.com
Navigate to Sign-In and Security
Enable Two-Factor Authentication
Once enabled, the App-Specific Passwords option will appear

Sync is slow (15-minute delay)

This is normal for iCloud calendars. Apple's CalDAV protocol doesn't support real-time webhooks like Google or Microsoft.

Why? We poll iCloud every 15 minutes to check for changes. This is the standard approach for CalDAV providers and balances responsiveness with server load.

Alternative: If you need instant synchronization, consider using Google Calendar or Microsoft 365 instead, which both support real-time webhooks.

How do I revoke an app-specific password?

If you need to revoke access:

Go to appleid.apple.com
Sign in and navigate to Sign-In and Security
Click on App-Specific Passwords
Find "SyncMyDay" in the list
Click "Revoke" next to it

You can also disconnect the calendar from SyncMyDay's Calendar Connections page, and we'll stop using the credentials.

Next Steps

Connect Another Calendar

Connect a work calendar (Google, Microsoft) to sync with your personal iCloud calendar.

Create a Sync Rule

Start syncing events between your calendars.

CalDAV Protocol

Apple iCloud uses the CalDAV protocol (RFC 4791):

Server URL: https://caldav.icloud.com
Principal URL: Automatically discovered via DAV service discovery
Authentication: Basic Auth with Apple ID + app-specific password

Polling Interval

Since CalDAV doesn't support push notifications, we poll every 15 minutes:

Uses PROPFIND requests to check calendar metadata
Only downloads changed events (using ETags)
Minimizes bandwidth and respects Apple's rate limits

Credential Storage

App-specific passwords are encrypted with AES-256
Stored securely in our database
Never transmitted in plain text (always HTTPS)
Immediately deleted when calendar is disconnected

Compatibility

This connection method works with:

iCloud.com calendars
Calendars synced to iCloud from iOS devices
Calendars synced from macOS Calendar app
Shared iCloud calendars (if you have write permission)

Limitations

No real-time sync: 15-minute polling interval
App-specific password required: Cannot use regular password
Two-factor authentication required: All iCloud accounts now require 2FA