Overview

SquadTrip can automatically post messages in your Group Chat at key moments during your trip planning journey. Milestones celebrate progress and keep travelers engaged, while welcome messages greet new travelers when they join the chat.

Chat Milestones settings showing welcome message, booking milestone, and trip countdown with toggles and editable message text

What Are Milestones?

Milestones are automated messages posted to your Group Chat when your trip reaches specific moments. They help build excitement and keep the group engaged as the trip date approaches.

Available Milestone Triggers

Milestone	When It Fires	Example Use
First Booking	When the first traveler books the trip	"We have our first traveler! The adventure begins!"
60 Days Out	60 days before the trip start date	"Just 2 months to go! Time to start packing lists"
30 Days Out	30 days before the trip start date	"One month away! Make sure your passport is current"
7 Days Out	7 days before the trip start date	"One week! Final reminders and packing tips..."
Day After Trip	The day after the trip ends	"What an amazing trip! Share your favorite memories"

Setting Up Milestones

Open your trip dashboard
Navigate to Group Chat settings
Find the Milestones section
For each milestone trigger, you can:
- Enable or disable the milestone
- Customize the message text that gets posted
Save your changes

When the milestone date arrives, SquadTrip automatically posts your custom message to the Group Chat.

Welcome Messages

Welcome messages automatically greet travelers when they join the Group Chat for the first time.

How It Works

A new traveler books your trip and joins the Group Chat
SquadTrip automatically posts a welcome message in the chat
The message can include the traveler's name and any custom greeting you've written

Setting Up Welcome Messages

Go to your Group Chat settings
Find the Welcome Message section
Enable welcome messages
Write your custom greeting — something warm and informative works best
Save your changes

Welcome Message Tips

Include practical info: "Welcome! Check the pinned messages for our trip itinerary"
Keep it brief but friendly
Mention any important group rules or etiquette
Point new travelers to key resources (FAQ, itinerary, packing list)

Best Practices

Don't over-message — the 5 milestone triggers are spaced out intentionally to avoid spam
Make milestones actionable — instead of just "30 days away!", add a call to action like "Make sure your travel insurance is sorted"
Use the Day After Trip milestone to collect feedback, share photo albums, or promote your next trip
Welcome messages set the tone — a warm, organized first impression makes travelers feel confident about the trip

Example Milestone Messages

First Booking:

"Our first traveler just signed up! The countdown to paradise begins. Who's next?"

30 Days Out:

"30 days until takeoff! Quick checklist: passport valid? Travel insurance? Sunscreen packed? Drop any questions below!"

Day After Trip:

"What. A. Trip. Drop your favorite photos and memories below! And if you loved it, stay tuned for our next adventure..."

Troubleshooting

Problem	Solution
Milestone message did not post on the expected date	Milestones are processed on a daily schedule. If the milestone date just passed, allow up to 24 hours for the message to appear. Also verify the milestone is enabled in your Group Chat settings.
Welcome message not appearing for new travelers	Confirm that welcome messages are enabled in your Group Chat settings. The message posts when the traveler first joins the chat, not when they book. If the traveler has not opened Group Chat yet, the welcome message has not triggered.
Milestone message posted with default text instead of my custom message	Make sure you saved your custom message after editing. Go to Group Chat settings, re-enter your custom text, and click Save. The next milestone will use the updated message.
I want to change a milestone message after it already posted	Posted messages cannot be edited retroactively. Update your milestone text in settings so future triggers use the new wording. You can always post a manual follow-up message in the chat.

Frequently Asked Questions

Q: Can I add custom milestone triggers beyond the five default options? A: No. SquadTrip currently supports five milestone triggers: First Booking, 60 Days Out, 30 Days Out, 7 Days Out, and Day After Trip. These are timed to key moments in the trip planning cycle and cannot be customized to different dates.

Q: Do milestone messages appear as coming from me or from SquadTrip? A: Milestone messages appear as automated system messages in the Group Chat. They are visually distinct from regular user messages so travelers know they are automated announcements rather than personal messages from the organizer.

Q: Will a welcome message fire if I add a traveler manually instead of them booking online? A: Welcome messages trigger when a traveler first joins the Group Chat, regardless of how they were added. If you manually add a traveler and they open the Group Chat, the welcome message will post for them.

Q: Can I disable milestones for one trip but keep them on for another? A: Yes. Milestone and welcome message settings are configured per trip. You can enable milestones on your group vacation trip while keeping them disabled on a smaller private trip, or vice versa.