Square: Service Recheck — 2026

Service Recheck: A follow up to our Service Review. What changed, what improved, and is it still worth it.

Square Service Recheck

When we first reviewed Square in September 2021, it was the friendly little card reader company. Mobile first. Easy to start. No contract. But light on integrations, light on online polish, and clearly built for the person at the front of the line more than the person running the whole shop. Fast forward to May 2026 and Square is a different beast. Same friendly on ramp, but a much bigger platform underneath.

Here is what changed.

The integration story flipped

Our 2021 review flagged “Handful of Integrations” as a real negative. That call has aged out.

Square now connects to nearly a thousand partner apps. Wix, WooCommerce, BigCommerce, QuickBooks, Xero, Etsy, Uber Eats, Zapier, and most of the tools a small business actually uses day to day. If you were sitting on the fence in 2021 because Square felt walled off, the wall is mostly gone.

Square AI showed up

In 2021, “AI in your POS” was a pitch deck phrase. In 2026, Square AI lives in your dashboard. It looks at your sales data, your inventory, and local market signals, then gives you suggestions you can actually use. Catch a slow day before it hits. Spot a product quietly outperforming. Ask questions in plain English instead of digging through reports. Still in beta, but useful enough that we noticed.

Online and in store finally talk to each other

In 2021 you could run a Square POS and a Square Online store, but the two felt like cousins more than siblings. Inventory sync was clunky. Customer data lived in different corners. Now it is one catalogue, one inventory, one customer list. A sale at the counter updates your website. An online order pulls from the same stock as your POS. For a shop that sells in person and online, this is huge.

The hardware lineup grew up

Reader. Terminal. Stand. Register. Kiosk.

In 2021 you mostly used a card reader and a phone. In 2026 there is hardware for almost every kind of business. Market booth, full retail floor, quick service restaurant, appointment based service, you can build the setup that actually fits. Square Kiosk in particular has gotten faster, which matters for quick service spots that want to take orders without tying up staff.

But here is what got worse

Not all upside thought, lets dig in.

Rates went up in January 2026. Free plan online rates climbed. For a store doing real volume, the difference adds up over a year. Always check the current pricing page before committing.

Account holds are a real risk. Square still occasionally locks up funds for ninety days or more after flagging an account. Rare, but if your cash flow is tight, you should know before you go all in.

Outages happen. Square has had a few service disruptions in 2026. Usually short, but a busy Saturday or a lunch rush is no time to find out the POS is offline. Build a backup plan.

What is still true from 2021

Some things did not change. That is a good thing. No subscription to start. Mobile first DNA. Loyalty and gift cards built in. Tailored apps for retail, restaurants, appointments, and general POS. Recurring payments still cost a bit more than standard tap. If you loved Square in 2021 for being simple and approachable, that core is still there.

Is it still worth it?

For solo operators, food trucks, market sellers, and small to mid retail or restaurants, yes. More than ever, actually. The platform is wider and deeper without losing its easy start.

For brands that want a fully custom storefront, or chains processing very high volume, the answer is the same as it was in 2021. Square will get you running, but you might outgrow it.

The biggest change is not any one feature. It is that Square is no longer just a starter platform. It is a real platform that happens to start easy.

If you wrote it off five years ago, it might be worth a second look.

Ready to set up Square for your business? Sign up through JBMD and get two hours of free online support to get you running. Depending on what you want to sell that call might be free to you.

Want the full breakdown? Read the updated Square Review.