Two-way texting lets your guests reply to your texts and have those replies land right inside TripWorks, in the Conversations tab of Lead Center. Your team can read and respond from one place instead of juggling personal phones or a separate texting app.

Setup is a one-time thing and takes about two minutes. It has two sides: a quick toggle inside TripWorks, and a one-time webhook configuration in your Twilio Console.

Before you start You'll need a Twilio account with your Account SID, Auth Token, and a Messaging Service already connected on the Twilio integration page (Settings → Integrations → Twilio). If those aren't filled in yet, add them first — two-way texting builds on top of your existing Twilio connection.

TripWorks sends and receives on the phone numbers in your Twilio Messaging Service. We don't buy or provision numbers for you — you manage those in your Twilio Console.

Part 1 — Turn on two-way texting in TripWorks

1. Go to Settings → Integrations → Twilio.
2. Scroll to the Two-Way Texting section below your Twilio credentials.
3. Switch Enable Two-Way Texting on.
4. Copy the inbound webhook URL shown in that section using the Copy URL button. You'll paste it into Twilio in Part 2.

The status indicator next to the toggle tells you where you are in setup:

Part 2 — Point Twilio at TripWorks (one-time)

This tells Twilio to forward incoming texts to TripWorks. You'll do it once in your Twilio Console.

1. Open your Messaging Service in Twilio: Console → Messaging → Services → [your service] → Integration.
2. Set Incoming Messages to Send a webhook.

3. Paste the webhook URL you copied into Request URL, and make sure the method is HTTP POST.

4. Turn on Advanced Opt-Out for the same Messaging Service (Opt-Out Management in that service). This lets Twilio handle STOP / HELP / UNSTOP keywords at the carrier level, which keeps your texting compliant. TripWorks does not intercept these keywords, so this step is required.

5. Save in Twilio.

Part 3 — Confirm it's working

You have two easy ways to check:

• Send test webhook — back on the TripWorks Twilio page, click Send test webhook. TripWorks sends a test message to itself and confirms the round-trip. A success means the connection is good.
• Send a real text — from any phone, text one of the numbers in your Messaging Service. Within a few seconds, the Last inbound indicator on the Twilio page updates with the sender and a preview, and the message appears in Lead Center → Conversations.

Once you see Active status and your test text arrives, you're all set.

Using Conversations

Everyday texting happens in Lead Center → Conversations.

• The conversation list (left) shows every SMS conversation, most recent first, with the guest's name (or phone number), a preview of the last message, a timestamp, and an unread indicator.
• Click a conversation to open the thread (center) — all messages in order, with a delivery status (sent / delivered / failed) on each message you send.
• Type in the composer at the bottom and click Send to reply. Your message goes out over Twilio and appears in the thread right away.
• The details panel (right) shows the guest's info, any linked trip, and internal notes your team can leave without texting the guest.

A few things worth knowing:

• Message length: texts over 160 characters send as multiple segments. The composer shows a segment counter so you know when a reply will split.
• Internal notes: use the notes toggle in the composer to leave a note for your team — it's saved to the conversation but never sent to the guest.
• Failed messages: if a text fails to deliver, you'll see a "failed" status with a retry option right on that message.
• Access: team members need Conversations access to see and reply. If a teammate can't see the tab, check their role permissions.

Troubleshooting

Status shows "Awaiting webhook." The toggle is on in TripWorks, but Twilio isn't forwarding messages yet. Recheck Part 2 — confirm the Request URL is pasted exactly, the method is HTTP POST, and you saved in Twilio.

Status shows "Webhook failing." Twilio is reaching TripWorks but the calls aren't succeeding. Open the inline webhook delivery log on the Twilio page to see the recent attempts, then use Send test webhook to retest after any change. If it keeps failing, reach out to support with what the log shows.

My test text never arrived. - Confirm the number you texted is actually in your Twilio Messaging Service. - Check Monitor → Logs → Messaging in your Twilio Console to see whether the inbound message arrived and what response it got. - Make sure two-way texting is toggled on in TripWorks — with it off, incoming texts get an automatic "this number is not monitored" reply.

Guests say they got a "not monitored" auto-reply. That's the default response when two-way texting is off. Turn it on (Part 1) and finish the Twilio webhook setup (Part 2).