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Square messaging is a two-way conversation between you and the customer through Square Messages. It stays anchored to the job, with the invoice link in the thread when they’re ready to pay.
Two-way messaging requires a paid upgrade — buy it before you start.Add Square Messages Plus in Square. That upgrade is what lets you start a conversation, which is exactly what the TireTutor flow on this page does. If your shop is on Square Free, Square routes you to Square Plus or Premium first.Without Square Messages Plus you can only reply to customers who text you first — the TireTutor dialog still opens, but Square blocks that first message. See Which plan you need.
It is not the same thing as Text the invoice link, which sends one ordinary text with a payment link and nothing more — and needs no Square plan at all, because TireTutor sends it. That’s covered below so you can tell the two apart in the send menu.

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Before you start

  • Square Messages Plus, if you want to start conversations. See the warning above and Which plan you need.
  • Your Square panel shows Connected. One-time setup — follow Square setup if the Square panel doesn’t show Connected, then confirm Connection health passes its invoice-writing check. No terminal is needed for anything on this page.
  • The customer has a mobile number on file. Square messaging and the invoice-link text both go to the number on the customer record, so add one first. Confirm the customer wants texts before sending.

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Turn on Square Messages

Square Messages holds the conversations you send through Square, not TireTutor. Turn it on once (Square’s free tier covers this):
1

Open Messages in Square Dashboard

Sign in to Square Dashboard, choose the Messages icon, then Get started. On the Square POS app instead: More → Add-ons → Messages → Add for free.
2

Upgrade to Square Messages Plus

This paid step makes the TireTutor flow below work. Add Square Messages Plus in Square. If your shop is on Square Free, Square routes you to Square Plus or Premium first.Skip this upgrade and you can only reply to customers who text you first.

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Which plan you need

Square gates two-way messaging behind the paid tier, so this decides whether the flow below works at all:
On Square’s free tier you cannot start a conversation. The TireTutor dialog still copies the number and opens Square Messages, but Square blocks the first message.Upgrade to Square Messages Plus before relying on this for customer payments. The dialog says as much: “Two-way messaging requires a paid Square upgrade.”
Square’s own guide: Set up and manage Messages.

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Message a customer from a work order

When: You want a two-way conversation with the customer about the job — including sharing the invoice link so they can pay from their phone. This is Square messaging: the message goes out inside a Square Messages conversation, the prepared text already carries the invoice link, and the customer’s reply lands threaded in your Messages inbox.
1

Open the work order

Open the work order with the balance the customer needs to pay. Check the customer’s mobile number.
2

Open the send menu

Next to the Send Invoice to Customer button, choose the unlabeled arrow — it opens a menu with more ways to send.
3

Choose 'Open messages — Text via Square Messages'

A short guided dialog does the fiddly parts for you.
4

Follow the dialog's three steps

  1. Choose Open Square Messages at the bottom of the dialog. TireTutor copies the customer’s phone number to your clipboard and opens Square Messages in a new browser tab.
  2. In Square Messages, paste the number into the “To:” field to start a conversation, or into the search box to continue one.
  3. Come back to the TireTutor tab, choose Copy message on the prepared text — a greeting with the invoice link already in it — then paste and send it in Square Messages.
The Text Dana through Square Messages dialog with three numbered steps, a copied phone number with a Copy button, a note that two-way messaging requires a paid Square upgrade, a prepared invoice message with a Copy message button, and Cancel and Open Square Messages buttons.

The guided dialog — phone number copied, message prepared, Square Messages one click away.

Your message shows as sent in the Square Messages thread, with the invoice link in it. The customer’s reply appears in the same thread.
Don’t see Open messages in the menu? Contact support to turn on the Square Messages shortcut for your shop. This TireTutor shortcut is separate from Square’s own Square Messages product.
This flow starts a conversation, so it needs Square Messages Plus. See Which plan you need. Replying to a customer who texted you first is free. Use Square’s guides: The same conversation works for anything about the job, not just payment — the prepared message is a starting point you can edit before sending.

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Text the invoice link (not Square messaging)

This is not Square Messages. The send menu offers Text the invoice link, with a sublabel that says the text sends automatically. TireTutor sends one text message with a link to the customer’s TireTutor invoice page. On an estimate, the same item reads Text the estimate link. The message sends immediately. For a Square payment link, use Contactless Payment Link / Tap to Pay in Square app under Process Payment. Square emails the link when the customer has an email address, and TireTutor texts it when the customer has a phone number. The result dialog tells you which delivery methods it used. Use it when the customer just needs the link. For a conversation around it, use Square messaging. The two are separate features, and this one doesn’t appear in your Square Messages inbox.
The Send Invoice to Customer split button with its menu open, listing Text the invoice link — Sends automatically by SMS, Open messages — Text via Square Messages, and View invoice — Open the public link in a new tab.

The send menu — TireTutor's plain-text invoice link at the top, Square messaging below it.

After it sends, the work order shows Last texted: with a timestamp, next to the Send Invoice to Customer button.

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View invoice

Select View invoice — Open the public link in a new tab from the send menu. TireTutor opens the customer’s invoice page in a new tab. This page belongs to TireTutor, not Square.

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Send a receipt by text

Receipts go by text from the Square side at checkout. The customer enters a mobile number on the receipt screen. Follow Square’s receipt guide.

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Answer customer replies

When a customer replies to a Square Messages conversation or a Square receipt, the conversation is in Messages in your Square Dashboard, not in TireTutor. A reply to TireTutor’s invoice-link text does not appear there.
Check Messages daily if you message customers through Square — a customer who replies “does this include the alignment?” is waiting on you there.
Run Connection health in the Square panel first. Square setup covers what each check means.
TireTutor must write a Square invoice before it can send a payment link. Follow the fix shown for Payment link enabled. Then select I’ve verified in Square — re-check.
Check the customer record. Square emails the link to the email address. TireTutor texts it to the phone number.

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Where to go next

Text to Pay and Tap to Pay

Manage a Square payment link.

Taking payments

Take payments and review payment history on a work order.