Every time Square rolls out an update, something else gets messed up. I do not understand why it is such a priority to keep shifting things around every few months with no meaningful improvements, instead of adding the features people actually need.
In California, we have a new tax as of January 1, 2026 called the Covered Battery Embedded fee, or CBE. Square lets you add it to your tax roster, but then it automatically applies it to every new item you add to inventory. As anyone can imagine, not every item has an embedded battery, so now every time you add a new product you have to manually deselect that tax. How hard is it to make that optional, so it only applies to the items that actually need it? That kind of update would have helped a lot more people than whatever pointless shuffle just happened today.
Square needs to remember that time is money. If business owners have to spend more time hunting for menus, deselecting boxes that should not be selected in the first place, and getting used to a new layout every few months, then Square is actively costing them money every time it decides to rearrange the system.
The iPad app crashes all the time. It throws three or four different pop-up windows every time the system goes to sleep. If you have not had a customer in a few minutes, the app suddenly needs to reconnect to the reader wirelessly while it is also physically connected to the iPad stand. It pulls inventory data from the internet instead of storing it locally, so while you are typing in an item, a pop-up appears saying the reader finally connected, and now you have to start typing all over again. It also does not use boolean operators in searches, so looking up an item cannot be approximate, it has to match exactly how it is written in inventory. Even uppercase and lowercase are treated differently. And the list goes on. There are so many genuinely useful updates that could be made to this system, but instead Square keeps wasting development time shuffling things around.
Sometimes it really feels like the people making these decisions do not have a clue what they are doing. They have clearly never spent a day working customer service or running a small shop, because if they had, they would understand how disruptive this system is. Tech bros do not know what it is like to work in the trenches, and quite frankly, Square should have a program where it sends its programmers into real stores to assess the actual needs of retail environments instead of guessing from an office in Silicon Valley.
This latest update doesn't work on certain browsers so now we need to have a specific browser for square. Well done square, you keep proving why finding a new POS system is now priority number 1 in my business.
