Square shipped a setting last week that lets you choose whether the cart sits on the left or the right side of the checkout screen. Each mode keeps its own choice, so your bar can run it one way and your quick-service window can run it the other. Had your favorite layout in your former job or former POS provider? No problem. Now you can make it your way.
If you have never stood behind a register, you think that is no big deal.
If you have stood behind one, you already know. The cart side decides which hand reaches, which way your eyes travel, and whether the kid on his second shift is tapping items or tapping the void where he thought the items were. A left-handed bartender on a right-cart screen fights the register all night. The screen was designed once, at install, for everybody, forever, and you lived with it. For twenty years I lived with it.
So no, it is not small. This is the bet I made in May, landing in real time.
The bet I made in May
Back in May I wrote about Block's February cuts. Over four thousand jobs, nearly half the company, announced with the quarterly results and framed as an AI restructuring. The skeptics said cost cut with a story on top. I said the ten weeks of shipping since then looked like something else, and that we would know which it was by the end of the year.
It is October 28. Here are the candy and nuts.
Square's public release notes did not exist before the cut. Volume 1 landed on April 9, six weeks after the announcement. Since then there have been fifteen volumes, every second Thursday, without a miss, each one riding a point-of-sale app version from 7.6 up to 7.30. One hundred forty-two features in the notes. Before April, the only public record was a feature log that dropped in lumps: thirty-three items one month, then twelve across the next three, then nineteen on a single day in late February. Since March that same log runs steady, roughly twenty-two items a month against fourteen before, and no month has gone quiet.
The smaller company ships more, ships on a clock, says so in public every two weeks, and does not call any of it AI.
Did you read that? They don't call it AI, because it isn't AI.
Where the AI actually is: upstream
I look at AI every day, and you know what? Those are features built with AI help. They are not AI. Is that not what owners actually want from tech? They want it to do something, not add to a to-do list. Block figured that out. They treated the to-do list as work that needed to get done, and here we have it: features and customizations rolling out every two weeks, based on what sellers asked for, not what someone who thinks they know best decided.
Everyone keeps waiting for AI to show up for business owners as a chatbot in the corner of the screen. Some of that is coming and some of it is already here. But that is not where the AI is doing the work in these notes. The AI is upstream. It is in the fact that a company half the size it was in February ships every two weeks like a metronome and the output is a cart you can put on the left. The AI is there to help you and answer questions, but these are real features being put into place in the real world.
That is what AI actually doing something for a business owner looks like. Not a feature with a sparkle icon. A platform that got fast enough to care about your left hand.
Build it your way
Thirty-one of the 142 items are about one thing: letting you set the system up the way you run, instead of the way the install tech guessed. Pull them out of the notes and read them in a row:
- Modifier sets that nest three levels deep, so "which bun, which cheese, which sauce" is one item and not a workaround.
- Per-item settings for whether the first size is pre-selected and whether the details screen is skipped when nothing is left to choose.
- Custom background colors on modifier tiles, so the eye finds "no onions" before the finger does.
- Identical items shown on their own lines or merged, your call, set per mode.
- Pin the tools you actually use to the bottom bar and bury the rest.
- Kitchen tickets with the modifier order you want, items sorted by seat, font size and footer padding you set.
- Kitchen display layouts up to ten columns, custom alert sounds, your own volume.
- Printer routing by category that new items follow on their own.
- And the cart, left or right, per mode.
In August I wrote a draft called Design Your Own POS, and the line I kept circling was that the right screen is customization done as subtraction. Take tools away until what is left is what this person, on this station, at this hour, actually needs. I was writing about where an AI layer could take that. What I did not expect was to watch the platform itself start handing the knobs over, two at a time, every other Thursday.
Two honest notes from the same release
The same October 22 drop that gave you the cart side also made the new Real-Time Check View mandatory for food and beverage. The notes say it replaces the old item-details layout and cannot be turned off. So the freedom is real, and it lives inside a frame Square has decided for you. If you run F&B, your screen changed whether you asked or not. Train your people before Monday.
Same release: open checks now count in the Sales report by default. Your "sales today" number includes tickets that have not closed. There is a filter to turn it off. If you reconcile against deposits, know that before you jump on the forums to rant.
That is what a two-week cadence looks like from the seller chair. Most of it is for you. Some of it is at you. All of it arrives on a schedule you can plan around, which was never true before.
The counter argument (and no, not the front counter through the pass)
Is too much choice actually bad? There is a paradox of choice in menu engineering. Some restaurants defy it, some die by it. What is true: the same system that is infinitely customizable still ships with a base setup. You do not have to touch any of it. What Block is doing is giving you the choice.
Where I stand
Same as in May. I am a Square Champion, I beta test, I run my operations on it, my consulting revolves around it, and I document what does not work on the line on Friday night in the places where the people who can fix it are listening. I chose the platform years ago because the barrier to entry was low and the APIs were open to an operator with no engineering team. The product was not perfect then and it is not perfect now.
But the bet is settled. The cuts did not slow the shipping. They preceded the fastest, most regular public release cadence I have seen from a point-of-sale company in eleven years on these systems. Occam's Razor still sits at the top of the register.
The release notes are public. Read the October 22 volume yourself: squareup.com/us/en/release-notes/release-notes-october-22nd. Then go flip your cart to the side your bartender has been asking for since the day you opened.
— Donnie