Square Appointments vs When I Work
Two scheduling tools side by side. Prices are the starting plan a small business would pick, in USD.
Short version
Square Appointments costs less for a six-person team.
When I Work fits retail shop, restaurant or café, trades or contractor.- Square Appointments fits service business, agency or studio.
| Compare | Square AppointmentsBlock | When I WorkWhen I Work |
|---|---|---|
| In one line | Free booking with unlimited staff calendars and Square payments | Shift scheduling and time clock from $2.50 a user |
| Starting price | Free | From $2.50/person |
| Six-person team | $0/mo | $15/mo |
| Plans | Free $0/mo per location; Plus $49/mo per location; Premium $149/mo per location; in-person 2.6% + 15¢ on Free (2.5%/2.4% on Plus/Premium); online 3.3% + 30¢ on Free | Essentials $2.50/user/mo; Pro $5/user/mo; Premium $8/user/mo |
| Pricing model | Free tier | Free trial |
| Free trial | — | 14 days |
| Users | Unlimited staff calendars | Per user |
| Both connect to | No shared connections on record. | |
| Also connects to | None in our catalog | Gusto, Rippling, QuickBooks Payroll, OnPay, Square Payroll |
| Team size | Just me · 2–10 people · 11–50 people | 2–10 people · 11–50 people · 51–200 people |
| Available in | US · UK · CA · AU | US |
| Phone support | Every plan (US) | None listed |
| Live chat | Plans not stated | Plans not stated |
| Support hours | Phone: 6am–6pm PT M–F for the first 90 days (Square Free only), 6am–6pm PT M–F (Square Plus only), 24/7 (Square Premium only) | Web form: Monday-Friday: 7 A.M. to 9 P.M. Central Standard Time, Saturday-Sunday: 9 A.M. to 4:30 P.M. Central Standard Time · Live chat: Monday-Friday: 7 A.M. to 7 P.M. Central Standard Time, Saturday-Sunday: 9 A.M. to 4:30 P.M. Central Standard Time |
| Incidents posted | 14 incidents posted on Block's status page, which covers all Block products and regions, in the 90 days to Oct 27, 2026; 0 marked major or critical by Block. Status page | 0 incidents posted on When I Work's status page in the 90 days to Oct 27, 2026. Status page |
| Capterra score | 4.5 / 5 from 263 reviews | 4.5 / 5 from 1,300 reviews |
| Trustpilot score | Not listed | 4.1 / 5 from 7 reviews (few reviews) |
| Fit: Retail shop | 50 | 85 |
| Fit: Restaurant or café | 15 | 88 |
| Fit: Service business | 90 | 65 |
| Fit: Agency or studio | 30 | 20 |
| Fit: Trades or contractor | 45 | 70 |
| Fit: Online store | 20 | 25 |
| Why people pick it |
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| Where it falls short |
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| Visit Square Appointments | Visit When I Work | |
Six-person prices are what a team of six would pay on the published plans; "Not listed" means those plans don't cover six. How we calculate prices
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