I’ve been with Square for over 8 years, and sometimes a feature that worked perfectly gets changed or removed—and it actually makes the workday harder instead of better.
Client Profile on the Appointments Calendar
When I click on a scheduled appointment, the client’s side profile pops up on the right side of the calendar. But the moment I click a different date on the calendar to the left, the client profile disappears. It didn’t used to do that.
This is frustrating because we lose the client’s information while we’re in the middle of scheduling additional appointments. Many of our clients have 4–5 future appointments, and it’s hard to remember all those dates while trying to avoid double-booking or scheduling them too close together. The client profile should remain visible no matter what date I click until I press the X to close it myself. Please bring this behavior back.
Also—look at how the client profile appears inside the Invoices page. That layout is perfect because you can click on the client's name and it doesn't open a new tab, and you can back out of the profile as well. The calendar should work the same way: view the profile on the same screen without opening a new tab. If we need to edit information, there can be an “Open in New Tab” button, but viewing should stay inside the calendar.
Invoices Need Exact Payment Time
Invoices show the date paid, but not the exact time—only “minutes ago” or “hours ago.”
Having the actual timestamp would make finding transactions much easier instead of doing deep searches to match payments.
Staff Need Invoice Payment Notifications
I’m a business owner and rarely work inside the spa. When a client pays an invoice, my staff receives no notification in their dashboard. They have to keep checking the invoice page all day to see if something was paid so they can schedule the client. That’s extremely time-consuming.
The notification bell should actually be useful. We should be able to choose what triggers alerts, such as:
And we should be able to choose banner, sound, or silent notifications. These alerts need to go to STAFF logins too—not just the owner—so they can do their jobs.
Service-Based Commission Structure
Every business is structured differently. I own the company but don’t perform services; I have contractors and employees, and each person has different commissions for different services based on negotiation.
Right now Square only allows one commission rate across everything. That doesn’t work for us.
We process over 300 transactions a week and must manually calculate who gets what for each service.
Under each staff profile we should be able to:
This would save hours of payroll work for accountants.
HR / Staff Notes & Documents
I see Teams and HR features being added, which is great—but we need a private administrative section inside each staff profile to document:
Tardiness or call-outs
Write-ups
Performance notes
Uploaded documents
Owners should control whether staff can see these records or not.
Deposit Rules for Problem Clients
We use “card on file” for cancellations, but when a client cancels late and their card declines, we lose the entire slot.
We should be able to mark specific clients as “Deposit Required to Book” instead of punishing all customers with stricter rules.
Right now we must manually send invoices or use Virtual Terminal, which is a lot of work. The system should enforce this automatically when that client books online.
Calendar Gap Time Helper
Many newer staff struggle with calculating time gaps. If they could drag or hover over a white space on the calendar and it showed:
“You have selected 1 hr 10 min gap”
it would help them know if a service can fit there. Poor time counting leads directly to lost revenue.
Automated Text Needs Day of Week
Confirmation and cancellation texts don’t show the day of the week—e.g., Tues 12/18.
This would reduce confusion for clients.
Service Availability by Specific Days
We need the ability to make certain services bookable only on specific days.
Example: a “Monday Special” should not be bookable on Tuesday. Even with it written in the description, clients still book and then argue.
Consent Forms Need Modernization
The built-in forms are not appealing and the wording feels scary. Clients don’t want to see the word “Contract.” “Consent Form/Waiver” is better.
I use Clever Waiver (which integrates with Square) because it’s:
Please look at how they structure forms.
Refund History Missing
Customer profiles show purchases but not refunds under activity. That history should be visible.
Smarter Square AI for Client Insights
Square AI should be able to:
Search clients by keywords from appointment notes
Summarize personality, incidents, preferences
Read internal notes like:
AI should feel like an employee who understands the company and clients—not just numbers.
Google Reserve & Groupon Bypass Policy
Even though my appointments are set to request + card on file, Google Reserve and Groupon bookings bypass this and allow clients to book without a card. This violates our policy and leaves providers unprotected. Those bookings should also require a request and card on file.
Declined Appointment Notes Bug
When declining a request, any note typed before pressing “Decline” does not save.
We must reopen the appointment to add it.
Also, the “Declined” label no longer shows in the client profile like Pending, Canceled, or Upcoming. Please bring that back.
I truly want Square to work for real, day-to-day operations. These changes would make an enormous difference for businesses like mine.
