Reports don't match, transactions are missing, and tips are missing as of May 19, 2025

[bab_jj]

We've been on with support for hours and nobody has any answers. For years all reports matched fine. As of yesterday (apparently timed with a UI change that doesn't seem to improve anything), we have transactions on devices that don't show on closing reports or transaction reports. Cash drawer reports no longer group sales by category even though the settings indicate they should. Transactions are randomly going into a mysterious not charged status for no reason at all. 

Is anyone else seeing these problems? We are going to get shutdown if we can't get these tips sorted out.

[ab123]

Since last week Tuesday all POS charges go into not captured category. I have spent hours on the phone and even escalated to management but they have not resolved it. I am extremely frustrated but cannot fix!!!!!

GO to transactions on dashboard and filter to not complete (Not captured) and you may find it there!

[Ellie_]

Hi there, @bab_jj & @ab123,

Thank you for posting about this, we definitely want to step in here and see how we can help! What devices are you two currently using on your accounts? This will help with troubleshooting steps and getting this resolved for you. 

[bab_jj]

This is NOT device centric issue. We have iPads, Square handheld devices, and white terminals. All of them exhibit the same problem. This only affects the restaurant app, the regular Square POS does not have the problem. Since Monday, May 19, approx 20% of our transactions get stuck in an "awaiting capture" status. We are unable to commit these transactions, only Square (on the backend) has been able to release them. The problem is that these transactions don't show in any drawer reports or on the dashboard (except on the transaction report under Awaiting Capture). So the tips are missing from the cash drawer reports and we can't pay out our tips. 

So we can't pay our people because of this bug that Square introduced in an update. 

The issue isn't specifically related to tips since transactions without tips also get hung up. The issue is NOT connectivity and we've proven that since we have multiple locations and every device can see the transactions in question even though the dashboard doesn't show them and the drawer reports to show them. 

The issue isn't device specific as indicated by the fact that 14 devices of different types have had the same problem after capturing the payment. 

Just to reiterate, this problem started for us on May 19, 2025. We had not made any changes to our settings since the pre-auth feature released a couple of months ago. We have been playing with settings since May 19 per advice from support reps. So far, we have no resolution and engineering has not been helpful or responsive. 

On the customer service side (full disclosure here), we have put in about 6 calls in the last 3 days and the quality of support reps is dramatically different across the board. I had two reps hang up on me after saying there's nothing they could do. I had two reps that helped release transactions on your backend, so kudos to those helpful people. 

But the issue is extremely painful and we are seriously at financial risk due to employment laws. 

I'm happy to share whatever data you want. And I'm extremely disappointed in Square support and the lack of escalation and sharing of information that has come with this issue. We've spent hundreds of thousands connecting Square to every facet of our business. And we are completely exposed without any means to get some ownership out of Square personnel. 

[bab_jj]

Engineering has the issue and has been very dismissive and almost impossible to communicate with. This "escalation" process that Square has is very poor at building any level of confidence in the user community. Engineering responds at most, once per day. They refuse to have any meetings or calls with us despite the mountain of data we've collected on the issue. 

This is the first time in the 3 years we've been with Square that I'm forced to consider an exit from the platform since we cannot use a system that throw us out of legal compliance with no indication of a solution on the horizon. 

[bab_jj]

We are now on day 11 without any reasonable response from engineering. Just so everyone that reads this can fully understand the issue. There is a combination of settings that can cause your system to appear to LOSE transactions. They aren't actually lost, but they do not captured correctly and there is no combination of reports within Square that will match until the issue is resolved. We have spent about 20 hours on the issue so far and even Square support issued their own ticket to the engineering team. I've received platitudes from engineering about where to click to capture a transaction and they refuse to believe that the option to capture the transaction is simply missing in about 20% of the cases. 

I'm trying to escalate this, but engineering seems incredibly stubborn on the issue and seems to believe that their software is perfect and can not have a bug (at least, that is my perception of their behavior). Of course, this begs the question on whether anyone in engineering is actually needed if their software has no bugs. 

I'll try to keep the community updated on the dismal failures of the escalation process at Square. I hope you aren't affected by this and suffering through the nightmare of being unable to pay your staff or reconcile your books. 

[bab_jj]

Four months on and this issue is still unresolved. No follow-up from engineering has been performed. Even our rep is frustrated by how unresponsive and difficult engineering is to deal with. Our experience with engineering at Square is that they do not care, and will not consider anything as a bug. 

Square simply doesn't seem capable of handling mission critical issues and the escalation that a strong B2B software vendor would be expected to provide. We are heavily invested in Square, but our little 3 location business seems to be about the max Square can handle. 

[theladyspantry]

I'm sorry that you had so much trouble. I hope you had your issues resolved by Square. If your issues were resolved can you let me know? It would help me to have faith that this means of communication (Community) actually works, because I find it hard to navigate and get answers to help me in my business. Thank you for your time.

[bab_jj]

I wish I could say that the community forum had an effect, but I cannot. Our rep is aware of the issue. And engineering is aware of the issue so I'm told since us customer plebes are not allowed to talk to those engineers on high. 

In short, the issue has NOT been resolved. It is clearly a bug and we have identified how it came to be. In May, Square published an update. In that update, the functional purpose of the setting "Reopen and keep payment method" was altered. If that feature is not selected and the "Reopen and remove payment method" is selected instead, our reports are working as expected. Of course, if we ever need to reopen a check, we lose the credit card or pre-auth and have to start over with payment methods. So it is wise to never reopen a check if the "remote payment method" is selected unless the guest is present. 

The bug impacts transactions when the "Reopen and keep payment method" is selected. If a transaction is paid without a credit card, things seem fine. But if a credit card is used, some transactions will be held open in a "pending" status and there is nothing you can do on the devices or on the dashboard to remedy the issue. We have recreated the situation under the watchful eyes of Square employees three times. If that setting is enabled and the payment method is a credit card, about 70% of the transactions will be held in a pending status and invisible to the employee with the open till. It doesn't seem to matter if the transaction has a tip or does not have a tip. We can't find any other characteristics to explain the results. In all three cases we had dozens of transactions get "lost" in the "pending" status and Square support confirmed it was a bug. 

Engineering, on the other hand, refuse to have a conversation with anyone on my team or even their own support staff. They only respond in thread format to their internal folks and in every case they come up with some wild story about us doing something to the tips to hold open the transaction. Of course, this happens on transactions without tips as much as with tips. But since we are all being kept away from the special "engineering" team, I don't have any further information. 

The support / development structure at Square is really messed up. This issue was such a major issue that we threatened to move our locations off of Square. I'm giving our rep a bit more time, but it seems that something is wrong with Square's priorities. So we may ultimately take our millions in credit card charges elsewhere. 

Sorry I don't have better news at this point in time. But I would certainly encourage all Square customers to press Square staff to respond with better solutions and concrete timelines. As a community, we can't run our businesses without accurate payment systems. And Square can't ignore everyone and stay in business. So communication is the solution.