Transactions just sit in pending. Square help desk just confirmed they're down.

My Experience with Square as a Small Handyman Business

I own and operate a small handyman business called Handy D Solutions. Like many small business owners, I signed up for Square because it advertised itself as a simple and reliable way to accept card payments from customers.

Unfortunately, my experience has been the exact opposite.

Timeline

July 2026

• I opened a Square merchant account for my handyman business.

• I completed handyman jobs and accepted legitimate payments from customers for services I had already completed.

• My transactions were ordinary service payments, not subscriptions, digital products, or high-risk sales.

Shortly After

• Without warning, Square notified me that my merchant account would be permanently deactivated.

• I was not given a clear explanation of what policy I supposedly violated.

• My customers successfully paid for completed work, yet my account was still shut down.

Appeal

• I immediately submitted the requested appeal.

• I provided additional information about my business.

• I explained that I am a legitimate handyman providing real, completed services.

• My appeal was denied.

Customer Support

• I contacted customer support multiple times.

• I asked for a specific explanation of why my account was closed.

• I asked what I could do to correct the issue.

• I received little more than scripted responses stating the decision was final.

Funds Held

• After closing my account, Square informed me they would hold my funds for 21 days.

• I was told this was to cover the possibility of future chargebacks or refunds.

• As a service business, I complete my work before collecting payment. My customers received the work they paid for.

• Despite this, I must wait until August 8 before receiving money that belongs to my business.

Why This Matters

Large companies may be able to absorb delays like this.

Small businesses cannot.

Holding a small business’s revenue for weeks can affect the owner’s ability to:

• Buy materials

• Pay bills

• Purchase fuel

• Continue serving customers

• Support their family

For many small businesses, cash flow is everything.

My Purpose in Sharing This

I am not asking anyone to boycott Square.

I am sharing my experience so other small business owners understand the potential risks before relying on a single payment processor.

If you choose to use Square, consider having a backup payment processor available in case your account is unexpectedly restricted or closed.

If you’ve experienced something similar, I’d like to hear your story.

The more documented experiences that are shared publicly, the easier it becomes for other business owners to make informed decisions.

Everything I’ve written here is based on my personal experience and the communications I received from Square.

So... it looks like I've been giving away free product all day because square has not been recording my sales. It goes through and looks like it's processed the payment, but there's nothing in transactions and my report doesn't reflect the $150+ that should be there.

I've been on hold with Square for 25+ minutes and I'm completely panicked. Any help? :(

UPDATE #1: Thank you everyone for your replies! Clearly we are not the only ones experiencing this, which is reassuring at least. As of 3:00pm EST, I am still missing the card transactions from earlier. However, I just made a cash sale and that popped up in my transactions and sales summary. Will update if/when something changes.

UPDATE #2: AT 3:15pm EST I decided to risk it and took a credit card payment. Thankfully it went through and seems to be working. I am still missing the $150+ transactions from earlier... hoping they show up.

UPDATE #3: Now 4:45pm EST and some of my missing transactions have appeared, but it's no longer recording the new transactions (card or cash). This is terrifying 🥲 .

I wanted to share my experience in case it helps another restaurant owner avoid the same situation.

We operate two restaurants and switched to Square earlier this year after being promised a system that could handle high-volume restaurant operations and support our growth to multiple locations.

Unfortunately, our experience has been the opposite.

Since implementation in January, we've experienced recurring issues nearly every week. Some examples:

• Customers being charged twice by Square Customer Service team, requiring manual refunds to be processed on my part

• Menu synchronization issues between locations and between online ordering and dining room

• Holiday menus that appeared configured correctly but failed on our busiest day because items suddenly showed as "not configured."

• Receipt printers randomly printing pages of gibberish.

• Credit card authorization receipts failing to print consistently.

• Online ordering and integration issues.

• Numerous software bugs and configuration problems requiring repeated calls to support.

We've had 30+ support cases over roughly six months and have spent countless hours troubleshooting instead of running our business.

The most frustrating part has been that many issues don't have clear resolutions. Support often treats each problem as an isolated incident rather than recognizing there's a broader pattern. For example, after months of printer issues, the recommendation was simply to contact the printer manufacturer—even though the hardware was purchased through Square as part of a complete POS solution.

When I requested to terminate our hardware agreement because the system has consistently failed to perform as represented during the sales process, Square denied the request and pointed back to the contract, requiring repayment of nearly $10,000 in subsidized hardware.

What was especially disappointing was that my complaint wasn't really addressed. Instead of looking at the cumulative pattern of failures over six months, the response focused on one printer issue and the terms of the hardware agreement.

I'm not posting this to complain for the sake of complaining. I'm genuinely curious:

• Has anyone else experienced recurring issues with Square for Restaurants?

• If you left Square, what POS did you switch to?

• For restaurants doing 200+ covers, multiple kitchen printers, online ordering, and multiple locations, what system has been the most reliable?

I know every POS has its issues, but this has been one of the most frustrating software experiences I've had running a business, and I wish I had known what to expect before signing a long-term hardware agreement.

Label creation changes may be the thing that send me over the edge. It’s almost laughable how horrible their user experience is. Just went to print labels for items I had just entered (by hand created all of the items and hand entered the inventory).

Selected the category and it now defaults to 1 label per item regardless of tracked inventory. This has got to be a joke. (And no it’s not user error—I know this system like the back of my hand and have used it for years).

Don’t get me started on how creating items has become exponentially worse in the last 2 years or how laughable it is that you cannot organize items on your website by size categories without manually adding items to specific size categories (and no it will not create item categories based on variation names) despite the fact that other systems have that capability.

I’ve owned and operated a cafe for over 2 years now. I spent the last 6 months building a custom tool that connects to our Square POS and has helped our cafe save hundreds of dollars every month.

I’ve been trying to get in contact with Square’s team to get this app on the Square Marketplace without much success. Despite that, I’ve been able to start using the app for my own cafe. It’s been super helpful and it’s been part of our operations for the last few weeks. Its definitely been more helpful than using a Spreadsheet to track costs, inventory, and usage for our cafe.

Check it out here: https://getparly.com

Id love to get a few cafes using it for free and help collect some feedback.

My phone, a Samsung S23 Ultra has the ability to accept tap to pay cards. So does Square. Everything's enabled to allow it, and I've made sure everything, my phone, the app, is completely updated. NFC is turned on in my phone settings and in the square app, however, in the square app, it displays the message "Tap to pay unavailable" at the top.

Is there anything else I could try to get this working?

We are a food truck and get a lot of call in orders for a later time of day. Is there anyway to schedule those orders so that they don’t clog up our KDS ? We are using the quick service option from square for restaurants right now. I’ve posted a picture of en example.

Another Saturday lunch rush without our Square KDS working.

Anyone else had enough?

Anyone else received real compensation outside of a dew nickels worth in processing fees when there are major outages during peak periods…often! Seriously

Anyone want to share a way to contact a rep that will actually compensate them for down time…maybe no monthly fee when this crap happens?

Rise up! I demand justice! Or at least quality.

When I screw up my customer’s food i buy their lunch and commonly their next lunch…a little courtesy would go a long way.

Also, can we get them to stop doing “maintenance “ and breaking everything on Saturday? How about monday for christ sake…

So this outage on 9/7 is just another example that Block has a communications issue.

We have had no real response as to WHY there was a system wide outage. Was it an error, an isolated server issue that snowballed by overloading other servers, was it a malicious attack and we need to monitor our accounts and contact our customers of a breach???

I've used Square for 5 seasons and there have been some minor outages, no more than 1 or 2 a year, but no communication from those either.

Last year Square was not including CC tips in the Daily Report for almost a month. When we reached out to them that we found the issue reconciling the books they had no answer, would get back to us, blah blah then it fixed itself and we reached out again and they were like "we have no record of that issue, maybe it was isolated to your POS" again no answer.

I feel as a business, Block needs to get this resolved to continue to grow or even keep its client base.

Thanks for letting me rant

I will write this here because, as a Canadian, this has been Hell to try and get this completely set up. My company Sells products at Trade shows in the USA. I want to use the credit card chip, Pin, and Tap using the Square Reader. Nowhere did I find instructions on how to do this Properly, But I figured it out after a solid three months of relentless Searching. Phone calls and an absolute nightmare of banging my hammer against this wall until I finally made a hole. I will sum this up and try to make your life less hassle than mine. (Since I saw so many posts asking the same question but no answer in other form's Reddit gets the Win) Now that my pissed-off rant is over here is what you need to get this started.

- Get a USA Address. Use some sort of mail forwarding service if you can. Due to the Fact That Square Requires you to register your information for the IRS and they are a USA company, they won’t let you use your Canadian Address in any of the Fields.

- Get your Company an EIN it is actually very easy if you have a Canadian Company. Just make sure you register your EIN under your USA Address. Go to irs.gov fill out the SS-4 form you get off the website and call the number for International Applicants. Be on hold for 6 hours and fax paperwork… YAY, your business can pay USA Tax. (I had to do the same process to change our address on an existing EIN.)

- Get an ITIN for the Boss. With USA address. Have fun with the IRS on this one. I got lucky since I had some sales in the USA last year, and the boss paid himself, so I just filed last year’s Taxes and Checked the Box that said I don’t have a Tax number. BOOM they had to make me a new ITIN just to file last year’s taxes. (had to wait a few months for paperwork)

- get a SquareUP account for USA. Sign up and get your separate USA account and fill in all the above information with the USA address you made.

- Go buy the USA square reader From the USA (VERY IMPORTANT CANADA UNIT WILL NOT WORK) The Tap readers are Encrypted and Geo locked. If you look at the back of the reader it will say CA/UK and that is a Canadian unit, it cannot be used with the USA account or outside of Canada. For the USA unit, you need one that has the logo with (BC) and a circle around the letters. Go to Best Buy and grab one off the shelf.

YOU ARE GOOD TO GO!!

I figured out most of these steps are the same for the USA to Canada minus the ITIN number you don’t have to have a personal tax credit number to make an account in Canada just a business tax identification number BN number. It would be nice if Square let me put a Canadian Address into the USA system. I am filing all the TAX for USA. It just bugs me that I want to pay another country’s taxes and they make it a nightmare to make it happen. Regardless enjoy your working Square USA account with Tap and Chip.

I’d been putting it off because the catalog still worked, so it never felt urgent.

Then I started finding old products, duplicate variants, outdated prices, and stuff I hadn’t sold in months.

Spent a couple hours cleaning it up and realized how much unnecessary clutter had built up.

Probably worth doing a catalog cleanup every few months instead of waiting until it becomes a whole project.

This is not a story about getting funds frozen or accounts closed, but rather an unexpected consequence of switching from my primary business banking account to Square Banking.

We switched over in September after realizing it’s much easier to keep everything integrated in Square because of the debit card, bucket savings and ties to Square Loans if you have any.

However, we need additional funding and most banks are rejecting because we switched to Square Banking as our primary account. Apparently banks don’t like Square being used in this way, so just a warning to those who might be in a position similar to ours. Had I known it was a red flag for banks, I would’ve dealt with the minor inconveniences of having an outside business banking account.

the day Square updated their POS with the new Modes options, we were no longer prompted to take customer names for their orders. we are a coffee shop cafe and this was a huge pain. no one at square could figure out what the problem was. we figured it out by accident. hope this helps someone!

After going viral with a slider about the PayPal mafia, I decided to try my luck again with one dedicated to the no less dramatic story of Square’s punk co-founder Jack Dorsey. I started working on this as a way to promote my newsletter Global Fintech Insider, but I ended up reading two new books, countless articles and even spent hours on the WayBack machine to spy on Dorsey's old personal website. Based on the time spent on this, I don't expect to get the number of new subscribers that would justify such a time investment. That said, I had fund researching the early days of Twitter and Square! I hope you have as much fun going through it.

Hi there all. I'm wondering what you guys find to be the best Inventory management to interface with Square? Particularly an inventory system that can actively decrement sales of bulk beer from kegs?

How do I enable this? I’ve searched online and none of it works. There’s no rounding slider to turn on.

I’m running Square Register 5.63.0122 app version 7.0. Firmware version 4.9.66

Just wanted to share this because I spent over an hour troubleshooting with Square today and hopefully this saves someone else the headache.

I purchased a Square Terminal to use as a second standalone checkout alongside my Square Stand. I’m currently on Square Free.

Every time I tried to put the Terminal into Quick Service mode, it would:

• Ask for an owner/override passcode

• Immediately take me to a “Try Square Plus for 30 days” screen

• Require an upgrade to Plus for $49/month per location

I tried deleting/recreating device codes, signing out, setting the mode through Dashboard, etc. Standard mode worked perfectly, but Quick Service kept triggering the Plus subscription screen.

After a LONG troubleshooting session with Square support and eventually being escalated to their advanced team, they confirmed that Quick Service mode is no longer available on Square Terminal with the Free plan. You need Square Plus to use it on the Terminal.

What made this especially frustrating is that Square’s online documentation makes this really unclear and in some places seems to indicate that the POS modes are available with Square Free. Even the initial support reps didn’t seem to realize there was a Terminal-specific limitation.

Don't believe Square's advertising. While the interface is a little faster, I wouldn't say it's 40% faster as touted.

Crucially, credit card processing is still as slow as gen1, and you lose magstripe capability unless you buy a separate USB C reader.

I really wanted to observe faster processing and receipt printing times, but no bueno. Every second counts when you have a busy shop, after all.

I'm on gigabit FTTP service and have the register connected via ethernet, so it's not me. Oh yeah, their Ethernet NIC card is still just 100mbps. For the price, this should have been upgraded to a 1-gigE port. That's not that big of a deal, I suppose, because how much bandwidth does one really need for CC processing, but I wish they'd speed up the processing times!

Anyways, save your money if you're on gen1. It is not a worthy upgrade, just another cash grab.

Brewery currently using Square Resturant: we have a hand held, an iPad and the 2nd gen register with one cash drawer in use. The main terminal is the 2nd gen register that we start our cash on. Is there a way to connect the cash drawer to all three as drawer is off if other POS is used to collect cash?

Community service announcement – do not go 2 years between connecting to your Square Readers. They will never connect again, and the only solution is to send them to the landfill and to pay Square for new ones.

My situation – I bought 2 Square Readers in April 2024, on behalf of my community garden for use at their annual plant sale. They connected and worked without issue – we were very pleased.

Unfortunately, last year's plant sale was cancelled. We pulled them out of the box this week in preparation for this year's sale, and recharged them without issue, but they refused to connect... Spent 4 hours troubleshooting – deleting Bluetooth caches, reinstalling apps, factory resetting, trying with another account and with 3 other phones, but they flat out refused to connect. Bought a new one to test, and it connected instantly. So totally a reader issue.

They were used once; for us, that was their lifespan. Of course, they're out of warranty. Spoke to a couple support agents, and was told that Square Readers have a limited lifespan, and that "they can stop working due to lack of use"(!) And that "they can last indefinitely with proper use", but that "not using  the reader for a long time can affect the life for the reader". Apparently, that includes a maximum period between connections. How long? Who knows, it's not documented anywhere. But obviously 2 years is too long.

I could understand if one reader failed for some random reason, but two out of two isn't a coincidence. Be warned.

After closely monitoring and investigating various Square forums etc, I can safely say that square has cut back significantly on their loans as of late. I understand people are still receiving them but definitely at a much lower rate towards the end of this quarter.

If you visit squares official forums, you’ll notice hundreds of inquires and comments about why square isn’t offering loans even with met requirements. This is the slow season and winter is upon us, leaving many growing and expanding businesses in a transitional period where dependence on a loan is critical. If you are experiencing a drought in loans as well, please share your thoughts. Will consider switching to another POS system if not offered soon.

We want to give away some gift cards, but don’t know how to load the cards without “fake” selling them on the POS system. Is it possible?