Sending iMessages from HubSpot with Tuco.ai

Watch the walkthrough:

Tuco.ai has a native HubSpot integration, so you can trigger iMessages directly from HubSpot workflows. This guide covers the setup, the sending rules, and the mistakes that get lines banned.

Before you start

You need an active Tuco line. If you haven't purchased a line yet, the integration won't be able to send anything.
Tuco is built for speed-to-lead: form fills, ad enquiries, inbound requests. It is not a bulk texting tool. iMessage will ban lines used for bulk sending, so treat it as a one-to-one channel.

Step 1: Connect HubSpot

1. Go to app.tuco.ai.
2. In the left sidebar, click Integrations.
3. Below Integrations you'll see API Keys, CRM, Connectors. Click CRM.
4. Click Connect HubSpot, then Connect with HubSpot.
5. Choose the HubSpot account/workspace you want to install on, then click Connect app and accept.
6. Back in Tuco, click Test scopes. You should see contacts and the other required scopes come back green. That confirms your leads can flow through.

Step 2: Build the HubSpot workflow

1. In HubSpot, go to Automation → Workflows.
2. Click Create workflow (top right), then From scratch.
3. Choose a Contact-based workflow and click Save and continue.
4. Set your trigger. For most teams this is a form submission. You can also use manual enrolment while you're testing.

Step 3: Add the Send iMessage action

1. In the action panel, scroll down the left side to Tuco.ai Texting Automation.
2. Click Send iMessage.

Then fill in the fields:

Phone number

Tuco only accepts E.164 format numbers (country code included, for example +14155552671). Use the search to pull in the phone number property from your contact record. If your CRM data isn't stored in E.164, run it through any free phone-format validator first and clean it up before you launch.

Message

Write it the way a human would write it. If you personalise with a token like first name and that contact has no first name on record, the message will not go out. Either backfill the property or leave personalisation out.

Attachment URL

Attachments and voice notes are supported, but only as a follow-up message. The first message to a contact must be plain text.
If you're attaching a voice note or file on a follow-up:

• Upload it in Tuco under Leads → Upload audio (drag and drop, then copy the URL), or
• Use any publicly accessible URL. Test it by opening the link in an incognito window. If it loads without a login, it works.
• YouTube, Vimeo, and other embed-only hosts will not work.

Line selection

• Leave this empty to send from any available line. This is what you want for the first message.
• Select a specific line if you want to route by sales rep or restrict sending to one number.
• Never type in a random phone number here. That's one of the two most common setup errors.

Click Save.

Step 4: Test it

1. Click Test, or turn the workflow on and use Manually enroll with your own contact record.
2. Choose individual contacts, pick yourself, save and enrol.
3. Open Enrollment history in HubSpot to see each step the contact went through. You want the action to show as succeeded.
4. If something didn't land, open Activity logs in Tuco to see exactly what happened to the message.

A note on testing: if you send the same message twice to the same contact, the second one gets deduped and dropped. That's the spam guard doing its job. When testing repeat sends, change the message slightly (even adding a full stop is enough).

Step 5: Turn on two-way replies inside HubSpot

Replies sync back to HubSpot automatically. You'll see sent and received messages on the contact timeline. To reply without leaving HubSpot, add the Tuco card to the contact record:

1. On a contact record, click Customize.
2. Select Default view.
3. Click the + button, go to Card library, search for Tuco, and add the card.
4. Save and exit.

You can now reply directly from the contact record. If you have a phone line attached, you can place calls from the same card.
Everything also syncs to the Tuco unified inbox, so your team can work from whichever surface they prefer.

Sending limits

Common mistakes to avoid

1. Phone numbers not in E.164 format. Missing country codes are the single biggest cause of "why didn't it send." Validate your CRM data before launching.
2. Links, attachments, or voice notes in the first message. These get dropped. The first touch has to be plain text, exactly like a human would send it. Media and links are fine from message two onward.
3. Personalisation tokens with no underlying data. If the contact has no first name and your message uses it, nothing goes out.
4. Typing a phone number into the line selection field. Leave it empty on first messages, or pick a real line from the dropdown.
5. Sending the identical message twice in a row to the same contact. It gets deduped. Check Activity logs to confirm.
6. Exceeding 50 sends per phone per day. Get another line. Pushing past the limit gets your line banned.
7. Using Tuco for bulk texting. It isn't built for it, and iMessage will ban you for it. Use it for speed-to-lead and one-to-one follow-up.

Getting help

If a message doesn't behave the way you expect, check Activity logs in Tuco first. It will tell you whether the message was dropped, rescheduled, or blocked and why. If you're still stuck, click Support in the app and raise a ticket.

Foxwell & Pierce, Inc. | 8 The Green Ste R, Dover, DE 19901
Tuco AI by Inboxpirates Consulting (Crewcharge Technologies Pvt Ltd and Foxwell & Pierce, Inc.). iMessage is a trademark of Apple Inc. Apple is not affiliated with, and does not endorse, this product.

Updated on: 31/07/2026