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How Sitter works with Google Calendar, Outlook, and Apple Calendar — real-time sync, imported bookings, recurring events, and sitter assignment.
Sitter works with your existing calendar. Connect Google Calendar for real-time two-way sync, or use email-based calendar invites with any calendar app. You can also create bookings by forwarding calendar events to Sitter.
Go to Settings and tap "Connect Google Calendar." Sign in with your Google account to grant calendar access. Once connected, Sitter monitors your calendars in real time using push notifications — new events, changes, and cancellations sync automatically within seconds.
You can choose which calendars to monitor. Tap "Edit calendars" in Settings to toggle individual calendars on or off. Sitter syncs events from the next three months. You can disconnect at any time from Settings.
When a sitter confirms a booking, Sitter creates a calendar event with the sitter's name, time, and any notes. If you cancel a booking, the calendar event is removed. When a sitter confirms, their name is also written back to the event description so you can see it directly in Google Calendar.
Changes flow both ways. If you move an event to a different time on the same day, your confirmed sitter receives a text about the time change. If you move it to a different day, the original booking is cancelled and a new one is created. Deleting an event in Google Calendar cancels the corresponding booking.
Even without connecting Google Calendar, Sitter can send ICS calendar invites by email when a sitter confirms. Enable calendar emails in Settings. The invite works with any calendar app that supports ICS files — Outlook, Apple Calendar, and others.
Sitter gives you two email addresses for creating bookings from calendar events. Each one works differently.
scheduler@trysitter.com — Forward or invite this address to create a booking and start outreach automatically. Sitter reads the date, time, and title from the event. If the title matches one of your occasions (for example, "Date night"), that occasion's sitter order is used. Matching checks the title first for an exact match, then looks for the occasion name anywhere in the title, then in the description. If no occasion matches, the booking is saved as a draft for you to review.
cal@trysitter.com — Use this when you've already confirmed a sitter outside of Sitter and just want the booking tracked in your calendar and bookings list. This creates an imported booking with no sitter texts and no credit used. If a sitter's name in the event title or description matches someone on your roster, they'll be auto-matched to the booking.
All-day events (without specific start and end times) are skipped. You can also toggle "auto-send" in Settings — when disabled, calendar events create draft bookings that you review and send manually.
Bookings created from cal@trysitter.com appear with an "Imported" badge in your bookings list and calendar. They include a link back to the original Google Calendar event. Imported bookings are view-only in the app — to change the time or cancel, update the original event in your calendar.
If an imported booking doesn't have a sitter (or the name didn't match anyone on your roster), you can manually assign one. Open the booking detail and choose a sitter from the dropdown.
For recurring events, Sitter detects that the booking is part of a series and asks whether to apply the sitter to all upcoming instances or just this one. Choosing "All instances" assigns the same sitter to every future unassigned booking in the series. Already-assigned instances are not overwritten.
Sitter tracks recurring Google Calendar events as a series. Each instance creates its own booking, but they're linked together. When you assign a sitter to one instance, you have the option to apply that choice across the entire series. Future instances that sync later are treated as separate bookings until you assign a sitter.
The Calendar tab shows all your bookings on a monthly grid. Dates with bookings are marked with color-coded dots: green for confirmed, yellow for outreach in progress, gray for imported, and red for cancelled. Tap a date to see the details, or scroll the upcoming bookings list below.
A "How it works" guide is available in Settings next to the calendar connection. It includes copy-to-clipboard buttons for both email addresses and quick tips on occasion matching, time changes, and cancellations.
All event times are converted to your family's timezone. Make sure your timezone is set correctly in Settings for accurate booking times.