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How to Automate Square Appointments

A tattoo shop's reminders, text rescheduling through Square Assistant and deposits at online booking all run in Square Appointments without staff. Checking that each custom design was approved in the artist's inbox, and logging spore test results from the lab's website, still falls to a person or to an agent like WebRun.

Square Appointments is where a tattoo shop books its artists and takes deposits

Square Appointments is the booking side of Square: the same account, card readers and payouts as the register, with a calendar of artists and services on top. Salons, spas, barbers, medspas, and tattoo and piercing shops book their clients through it.

A shop's week runs through it. Walk-ins, touch-ups and custom pieces go on the calendar under an artist, and apprentices and the shop manager work from the same calendar. On the Premium plan a station can be set up as a resource, so a four-hour session books the chair along with the artist.

Clients book from the shop's online booking site, from Instagram or through Square Go, Square's free marketplace app for beauty and personal care. A deposit, fixed or a percentage of the service, is taken when the client books online. Contracts and other documents can be attached to the booking, and aftercare and merch sell at the same checkout as the session.

A walkthrough of the Square Appointments dashboard, showing how to manage appointments, clients and staff from one place. Video: Square Appointments Dashboard Walkthrough, from Square on YouTube, 4 min.

A custom piece needs a deposit, a signed form and an approved design

Before a long session the shop manager wants three things settled: the deposit paid, the consent form signed and the design approved. The first two are in Square. The third usually is not, because the sketch and the client's yes live in the artist's email or DMs.

So the evening before a big day, the manager opens each booking, checks the deposit and the form, then scrolls back through messages to find the approval. A session with no signed-off design turns into a nervous phone call in the morning, or an artist drawing at the station while the client waits.

Other jobs come round on a clock. Touch-ups fall due inside the window the shop offers. If the shop sterilises with an autoclave, a spore test goes to a mail-in lab on the schedule the health department sets, the result appears on the lab's website, and the manager copies it into the log an inspector may ask to see.

Custom sessions cleared the night before Each of tomorrow's custom bookings checked for a paid deposit, the contract attached in Square and a design the client approved in writing.
Touch-ups offered inside the window Clients whose sessions in Square fall inside the shop's touch-up window sorted by artist, with an offer drafted for each.
The spore test logged when it lands The autoclave result read off the testing lab's website and written into the shop's log, with a flag if it is late.

Square Appointments records the deposit and the contract, not the design approval

Square's waitlist, which needs Plus, texts and emails waiting clients when an opening comes up, and Plus also adds a cancellation policy with no-show fees and booking with more than one artist. Square Assistant answers client texts at any hour, confirming, cancelling or rescheduling appointments straight into the calendar, and reminders go out automatically by text or email on every plan.

Premium adds stations as bookable resources and per-artist commissions, flat or tiered. Square Marketing, sold separately, sends automated email and text campaigns for flash-sheet sales or aftercare products.

The client's yes to a design usually comes back in the artist's email or Instagram DMs, outside Square's own messages, and a thread is the only record of it. The spore test result is posted on the lab's website.

Square Assistant text thread on a phone: a client asks to reschedule, an automated reply offers three times on Thursday, Sep 15 to pick by letter, the client answers a, and a second automated text confirms the 5 PM appointment with Iris & Onyx.
In this example thread, Square Assistant offers three Thursday times by text, and the client's one-letter reply moves the appointment to 5 PM. Screenshot: Square Appointments on squareup.com, captured 12 October 2026.

Only the custom sessions with a gap reach the artist the night before

The artist's message the night before names only the custom sessions with a gap: no deposit in Square, no contract on the booking, or no clear yes to the design in the thread with that client. The manager sees every session for the next day marked cleared or not, and has an evening to chase the gaps. For sleeves and back pieces the same check can run three days out, which leaves the artist time to redraw.

The artist approves a drafted offer for each client whose session falls inside the shop's touch-up window, and a few weeks later a second draft asks the same clients for a healed photo, for artists who want one for the portfolio.

The autoclave log gets each spore test result with its date and the load it covers once the lab posts it. The manager still signs it, and a late result shows up in the week it was due.

One pass after closing covers Square, the design inbox and the lab's results page

The deposit and the contract are on the booking in the Square Dashboard, and the yes to the design is in the client's thread with the artist. WebRun is an AI agent that works a real Chrome browser, signed in as you. One pass after closing covers the Dashboard, the thread for each custom session and the lab's results page, and the spore result lands in the shop's log in Google Sheets.

It takes and refunds no deposit in Square and sends clients nothing. Touch-up offers go into the shop's email as drafts, each artist choosing which ones go out, and a person still signs the log.

Deposit tracking is the workflow here that chases what this check only finds; aftercare messages, touch-up reminders, artist schedules, a sales digest and a commission report run on the same Square records.

Square Dashboard appointment for a sample client with Cancel Appointment and No-Show links. A No-Show dialog says the appointment moves to the client's history, with an unticked box to charge a $25.00 no-show fee, a notification field, and Back and Mark as No-Show buttons.
A sample booking in the Square Dashboard with the No-Show dialog open and the box to charge a $25.00 no-show fee left unticked. Screenshot: Appointment Cancellation Policy Template on squareup.com, captured 12 October 2026.

Questions people ask

Does this cover Square's register too?

No. This page covers the appointments side of Square: the calendar, the artists, deposits and booking documents. The register and the day's takings have their own guide to Square.

What counts as an approved design?

A clear yes in writing, in the latest messages of the thread with that client. Anything short of that, such as a question about the linework or a reply that only says thanks, is flagged for the artist, who makes the call.

Do approvals sent through Square Messages count?

Yes. Square Messages keeps texts and emails with each client in the Square Dashboard, so a yes written there counts the same as one in the artist's email.

Will it take or refund a deposit?

No. Square takes the deposit when the client books online, and a refund is issued from Square by someone in the shop. The agent only reports whether each custom session has one.

Our artists answer clients from their own Instagram accounts. Can it still find the design approval?

Only in the inboxes it is allowed into. Some shops route design talk through one shared email address; others connect each artist's inbox or Instagram account. Every reply in those threads is still one the artist writes.

Sources

6 ready-made Square Appointments workflows

Each one names the apps it touches and the exact steps it takes. Open one to read what it will do, then turn it on.

Automated Tattoo Touch-Up Reminders
WebRun checks Square Appointments for tattoo sessions completed 6 to 10 weeks ago, drafts a touch-up reminder text via Twilio for each eligible client, and queues the messages in Slack for approval before sending.
Square Appointments›Twilio›Slack
Automated Tattoo Studio Sales Digest
Every evening, WebRun pulls the day's completed transactions from Square Appointments, totals revenue by artist, and posts a clean sales digest to Slack so the studio owner sees how the day performed.
Square Appointments›Slack
Automated Tattoo Deposit Tracking
WebRun checks Square Appointments for upcoming bookings, flags any that are missing a Stripe deposit, drafts a polite payment request, and alerts the team in Slack.
Square Appointments›Stripe›Slack
Automated Tattoo Commission Report
Every Monday, WebRun pulls the previous week's completed transactions from Square Appointments, calculates each artist's commission or booth-fee split, writes the results to Google Sheets, and posts a summary to Slack for the studio owner to review.
Square Appointments›Google Sheets›Slack
Automated Tattoo Artist Schedule Digest
Every morning, WebRun opens Square Appointments, compiles each artist's appointments for the day, highlights any gaps or back-to-back bookings, and posts individual digests to Slack so every artist starts their shift prepared.
Square Appointments›Slack
Automated Tattoo Aftercare Messages
WebRun checks Square Appointments for sessions completed yesterday, drafts a day-1 aftercare text and a week-1 heal-check text via Twilio, and queues both in Slack for approval before sending.
Square Appointments›Twilio›Slack

Want one of these running on your own Square Appointments?

Show WebRun the process once and it will run it on schedule, in your own private browser environment.