Trip Insurance is now live for U.S. beta users

Quick follow-up/clarification on trip insurance availability:

• Trip insurance is offered to guests when check-in is 30 days or more away.
• For bookings within 30 days of check-in, trip insurance is still available if it’s purchased within 4 days of booking.

Practically speaking, for guests who book within 30 days of check-in, as long as they enter the Guest Portal within the first 4 days after booking, they should still see the option to purchase trip insurance.

As mentioned above, we’re actively pushing for this 4-day window to become more flexible and will share updates as soon as we have them.

Oh! So if they book Dec 20 for check in Dec 25 they can buy all the way til Dec 24? 4 day window is great! I need to figure out how to send a reminder at day 3 

​@mrotman In theory, yes, however we actually received an error during a close-to-check-in booking this week, so we’ve had to add a 2-day buffer (instead of 1) for the time being. Timezone’s make date calculations a little tricky sometimes so this ensures guests are only offered trip insurance when they should.

Once we have absolute clarity on the new, more flexible timing window, we’ll be sure to update here!

Thanks, I'm just trying to rush this because we are headed into the most busy two weeks of our year, the most expensive two weeks every year as well. Plus we're getting rain, mudslides and huge snow storm so everybody wants insurance and I want to remind them they can get it. And now I'm not sure what to do. Obviously it would be a huge upsell for me to do that now with the big ticket days and also to ensure that the renters feel safe with the upcoming weather. I'm not even sure what kind of climbed automated message I could send through hospitable? Even if it's a day after they book. 

​@mrotman Totally hear you, this is exactly the kind of scenario where trip insurance is most valuable.

Given the timing and the moving pieces around eligibility, the safest approach for now is to recommend trip insurance in your guest messaging, while making it clear that availability isn’t guaranteed. Eligibility depends on the guest’s reservation details (timing, location, etc.).

Perhaps something along the lines of:
“Trip insurance may be available for your reservation and can help protect against unexpected events like weather disruptions. Availability and pricing are determined by the insurance provider and aren’t guaranteed for every booking.”

That way you’re encouraging guests to check early (which helps with upsell and peace of mind), without creating confusion or frustration if the option doesn’t appear for them.

Once we have full clarity and more flexibility around the timing rules, we’ll absolutely share best-practice guidance on reminders and automation. We know this is a high-stakes period and appreciate you flagging the real-world feedback here!