How to send a win back campaign in Square Appointments

Build your win back list

A win back list has two groups: customers who cancelled, paused or stopped booking in the last six months, and intro clients who never signed up. Both live in Square Dashboard under Customers > Customer directory.

Past customers

1. Open the Lapsed smart group. It holds former regulars who have not visited in six weeks. Square's Regulars group counts three visits in six months by default.
2. To change the rules, select the group and choose Actions > Edit Group. Or click + Add filter, add your rules, click Apply, then Save as group.
3. If you bill memberships through Square subscriptions, open Subscriptions under Orders & payments (or Payments & invoices, or Payments) and look for the status Canceled or Paused.
4. Add anyone the filters miss by hand: + Create group, then Manual group, select the customers and click Create group.

Square's filter help does not name every filter. Pick the purchase or visit filter on your screen. The directory has an Import/Export button, but the help pages only cover importing.

Intro clients who never joined

Square's directory help shows no lead status, so mark these people yourself. Go to Settings > Configure profiles > Create Custom Field and add a Toggle field such as "Intro only". A visible Toggle field becomes a filter on its own, so you can save it as a group. People who joined your mailing list through Square's sign up tools sit in the Collected Emails group.

Start with the most recent

If the list is long, send to the last two months of leavers first, then months three to six. Recent leavers are the easiest to win back.

Send the three emails

Go to Customers > Marketing > Campaigns, click Create campaign and choose Email. Pick your location and objective, then click Design. Click Select Audience, choose Custom and pick your win back group. Finish with Review Campaign, then Schedule or Send Now.

• Email and text campaigns need Square Plus or Square Premium. Plus is listed at $49 and Premium at $149 a month per location on Square's pricing page in October 2026. Both include unlimited email campaign sends.
• To schedule, click Review Campaign > Schedule and set the time. You can build the Day 5 and Day 10 emails on Day 1. To stop one, select it, click Cancel, then Cancel Campaign.
• Square says an email gathered only from a receipt, invoice, appointment or loyalty sign up cannot get campaigns. The exceptions are customers whose consent you recorded or imported, or who used a Square sign up tool. Check the Subscribed customers group, or the Marketing section of each profile.
• The help pages do not say which address campaigns come from or where replies go. Include yourself in the group to check.
• The help pages describe customers opting out through Manage preferences on a Square digital receipt. The import tool cannot resubscribe them.

Send the two texts

Square texts in two ways. Text message marketing sends one text to a whole group. Messages handles one to one conversations.

• To set up texting, go to Customers > Marketing, click Create Campaign and choose Text Message. Your sender name starts every text. Square then verifies a toll free number, which takes two to three business days on average and up to 14. Campaigns stay as drafts until then.
• Square Plus includes 500 texts a month, then 3 cents each. Square Premium includes 2,500, then 1.5 cents each. Square Free has no text marketing. Prices as shown on Square's pricing page in October 2026.
• Customers agree to texts at your point of sale after paying, or by texting your sign up number. Find it under Customers > Marketing > Settings. Setup asks for a coupon to give people who opt in.
• To send, edit the message, choose your Audience, click Next, then Send Now or Schedule to Send.
• The help pages give no length limit for campaign texts and do not say whether customers can reply or how STOP works. Put your booking link in each text and ask people to mention your code word at the front desk.
• On Plus or Premium, Messages can start a text with one customer from your business number. Confirm consent first; for marketing content, Square asks the customer to agree too.

Your ten day plan in Square Appointments

The five messages, ready to fill in, are on the win back email templates page. Both texts there already fit in 160 characters.

Can Square Appointments run it for you?

Partly. Automated email and text campaigns are part of a Plus or Premium subscription. Square's marketing page lists bringing back lapsed customers as one use.

• For an automated text, choose Create Campaign > Text Message, pick an objective, add a message and coupon, then Activate Now. It goes to every customer who meets the rules. Edit it under the Campaign tab > Automated Text Message.
• The help pages do not describe a series of messages with set gaps, or the timing of the lapsed automation. So run the ten days as scheduled campaigns.
• Repeat this campaign sends weekly or monthly, which does not fit a ten day plan.
• A lapsed automation running during your ten days could double up on people. Turn it on after Day 10 instead.

See who came back

• Make your code word a coupon: Customers > Marketing > Coupons > Create Coupon, enter COMEBACK, then Activate. Codes ignore capital letters, and Square tracks redemptions. Percent off coupons work in store only.
• In Customers > Marketing > Campaigns, click a campaign to see its opens, clicks and purchases.
• Reports > Operations > Team performance, then See details next to Client retention, compares returning clients with all clients. Square lists it for Square Appointments Plus or Premium, and for Square Premium with advanced bookings capabilities. Anyone who visited in the year before your dates counts as returning.
• Customers > Customer directory > Insights > Visits counts visits from card payments only. Cash visits are left out.

Watch out for

• The default Lapsed group only holds former regulars. A client who came once or twice never enters it, so build your own group too.
• Reminder emails are off unless you switch them on at Review & Send. If on, they go to non openers five days later, on top of your Day 5 email. Coupon campaigns also go again before the coupon expires. Reminders cannot be turned off after sending, so leave them off.
• Start text setup three weeks ahead, since number checks can take 14 business days.
• The help pages do not say whether a scheduled campaign rechecks its group at send time. Look over the group before each send.
• Duplicate profiles can raise Square Marketing subscription pricing. Duplicate Suggestion lets you merge them, but a merge cannot be undone.

Sources

• Create customer groups and filters (Square, April 2026)
• Add new customers to your Customer Directory and custom fields (Square, April 2026)
• Collect customer information (Square, April 2026)
• Edit, merge, or delete customer profiles (Square, April 2026)
• Manage item subscription plans (Square, April 2026)
• Create marketing campaigns and Schedule marketing campaigns (Square, April 2026)
• Unsubscribe from Square Marketing emails (Square, April 2026)
• Set up text message marketing (Square, April 2026)
• Set up and manage Messages (Square, April 2026) and Message your customers (Square, September 2025)
• Create vanity code coupons (Square, April 2026)
• Email marketing campaign reports, team performance report and customer insights (Square, April 2026)
• Square Marketing and Text Message Marketing (Square, seen October 2026)
• Square pricing (Square, seen October 2026)