How to Integrate iCloud Calendar with Enrollio

Connect your iCloud calendar to Enrollio to automatically sync tours, meetings, and appointments. When you book a center tour or schedule a parent meeting in Enrollio, it'll appear on your iCloud calendar—and when you block time on your iCloud calendar, Enrollio knows you're unavailable.

Important: Enrollio syncs events from iCloud to block your availability, but parent/family records are not created from iCloud events. Create tours and appointments directly in Enrollio to manage your family contacts.

What You'll Need

  • An iCloud account with two-factor authentication enabled
  • An app-specific password from Apple (we'll walk you through creating this)

Step 1: Create an App-Specific Password in iCloud

Apple requires a special password for third-party apps like Enrollio. This is different from your regular Apple password and keeps your account secure.

Enable Two-Factor Authentication

  1. Go to appleid.apple.com and sign in
  2. Look for the Security section
  3. If two-factor authentication isn't enabled yet, turn it on now

[SCREENSHOT: Apple ID Security section showing two-factor authentication enabled]

Generate Your App-Specific Password

  1. In your Apple ID account, click into Sign-in and Security
  2. Select App-Specific Password
  3. Click Generate an app-specific password
  4. Name it something you'll recognize, like "Enrollio Calendar"
  5. Click Create

[SCREENSHOT: Apple ID app-specific password generation screen with "Enrollio Calendar" entered as the label]

Pro Tip: Copy this password immediately and save it somewhere safe. Apple only shows it once. You'll need it in the next step.

Step 2: Connect iCloud to Enrollio

Now you'll use that app-specific password to link your iCloud calendar.

  1. In Enrollio, go to Settings → Calendars → Connections
  2. Click + Add New
  3. Click Connect on the iCloud Calendar option
  4. Enter your iCloud Apple ID (your email address)
  5. Paste the app-specific password you created in Step 1
  6. Click Connect

[SCREENSHOT: Enrollio calendar connections page showing the iCloud connection modal with Apple ID and password fields]

Step 3: Configure Your Calendar Settings

Tell Enrollio which calendar to use for new events and which calendars should block your availability.

Set Your Primary Calendar

  1. Go to Settings → My Profile → Calendar Configuration
  2. Click Edit next to "Primary Linked Calendar"
  3. Choose which iCloud calendar should receive new tours and appointments you create in Enrollio
  4. Click Save

Events you create in Enrollio will now appear on this calendar. Events you create on this calendar will sync back to Enrollio.

[SCREENSHOT: Calendar Configuration panel showing primary linked calendar dropdown with iCloud calendars listed]

Add Conflict Calendars (Optional)

Conflict calendars block your availability in Enrollio when you're busy elsewhere—like personal appointments, staff meetings, or holidays.

  1. In Calendar Configuration, click Edit next to "Conflict Calendars"
  2. Select any calendars that should block your availability:
    • Your personal iCloud calendar
    • US Holidays
    • Team members' calendars
  3. Click Save

Note: Only events marked as "Busy" in iCloud will block your Enrollio availability. Events marked as "Free" sync to Enrollio but don't block scheduling.

[SCREENSHOT: Conflict calendars selection modal showing multiple calendar options checked]

Troubleshooting

Can't Connect Your Account

  • Double-check you're using the app-specific password, not your regular Apple password
  • Make sure two-factor authentication is enabled on your Apple ID
  • Try generating a new app-specific password and connecting again

Events Aren't Syncing

  • Verify you selected the correct primary calendar in Calendar Configuration
  • Make sure new iCloud events are being created on the calendar you linked (not a different one)
  • Check that events are marked as "Busy" if you want them to block availability

Getting Double-Booked

  • Add the calendars causing conflicts to your Conflict Calendars list
  • Confirm events on those calendars are marked as "Busy" not "Free"

Frequently Asked Questions

Does iCloud sync both directions?

Partially. Events from your primary linked calendar sync to Enrollio, and new tours/appointments from Enrollio sync to that calendar. However, blocked time you create manually in Enrollio won't sync back to iCloud. Only scheduled tours and appointments sync both ways.

Can I connect multiple iCloud calendars?

Yes. Each team member can connect their own iCloud account. You can also set up multiple iCloud connections if needed.

Will events from conflict calendars block my availability?

Yes—that's what they're for. If you have a personal appointment or team meeting on a conflict calendar, families won't be able to book tours during that time. The event must be marked "Busy" (not "Free") in iCloud.

Can I connect calendars I've subscribed to in iCloud?

No. Enrollio can only connect to calendars you own directly in iCloud, not subscription calendars (like public calendars you've added via URL).

Will Enrollio create parent records from iCloud events?

No. Events from iCloud only block your availability—they don't create family contacts in Enrollio. To properly track tours and manage families, create appointments directly in Enrollio.