---
title: "Ten conditions, one guest | Conditional Rules"
description: "Most upsell software runs off one field. Check-in minus seven. On that day everybody arriving next week gets the same message with the same four things in it, whatever is already booked in their week."
url: "https://www.holidayhero.com/videos/ten-conditions-one-guest-conditional-rules"
published: "2026-11-05T16:37:15+00:00"
updated: "2026-11-05T16:37:15+00:00"
---

# Ten conditions, one guest | Conditional Rules

- **Watch** — [YouTube](https://www.youtube.com/watch?v=wY2GxLHC1vE)
- **Duration** — 8:19

Most upsell software runs off one field. Check-in minus seven. On that day everybody arriving next week gets the same message with the same four things in it, whatever is already booked in their week.

Follow one guest through that. She booked the Thursday boat trip three weeks ago, on your own screen. On Saturday morning she gets an email selling her the Thursday boat trip. She reads it one of two ways and both cost you something: either you do not know what she booked, which is worse than silence because she already told you, or you do know and you are selling anyway.

This video is about the alternative. A message template can carry conditions, and a condition is a test we run against the reservation at the moment the message would send. It goes out only where every test passes. There are ten of them, and we walk through all ten.

THE TEN CONDITIONS

1. Date range. Check-in or check-out falling inside, or outside, a period you set.
2. Check-in status. Whether the guest has checked in yet at the moment the message would send.
3. Stay date. Whether one or more specific dates fall anywhere inside the stay.
4. Day of week. Which weekday the arrival or departure lands on, read in the property's own timezone.
5. User count. How many guests have registered or been invited to the guest portal. Not the party size on the booking, which is the thing most people assume it means.
6. Guest group. Whether a guest on the reservation belongs to one of your own groups.
7. Reservation source. Where the booking came from. An OTA, or direct.
8. On the itinerary. What is, or is not, on this guest's plan. The one this week is about.
9. Length of stay. How many nights, counted as calendar nights in the property's timezone.
10. Guest sentiment. How the conversation with this guest is actually going.

Conditions combine with AND, so every active one has to pass. There is no OR: an either/or is two templates.

#hotelsoftware #hospitality #hoteltech #upselling #hotelmanagement