thread Re: Authorization On Square Stand Requires 2 attempts..... in Payments Troubleshooting

Authorization On Square Stand Requires 2 attempts.....

MountainHouse — Sat, 20 Sep 2025 09:43:01 GMT

Since the last update for Square for Retail on the iPad stand came through late last week, all of our transactions paid by credit card are taking two attempts. This is also occurring on Restaurant on the Square Stand. If the client uses a chip card the screen gets stuck indefinitely on "Preparing Payment", if the client uses tap to pay, apple pay or google pay, the green light turns off on the reader, and nothing at all happens on the screen. In both cases we must cancel the sale and try again. It always goes through on the second try. We have done all the obvious, checked for updates, terminated the app, hard reset the iPad, nothing makes any difference. I have called support and reported this and nothing has changed, nor has issquareup.com been updated to report a known issue. This is beyond ridiculous at this point and its frustrating customers as they are worried they will be charged twice. Would someone please acknowledge this issue and get it fixed! Thanks! 🙂

Re: Authorization On Square Stand Requires 2 attempts.....

Candlestore — Mon, 24 Apr 2023 11:58:58 GMT

@MountainHouse ;

I complained about this issue and the Black Square that would show up on Ipads for 5 seconds or so saying X item was added to cart. Square fixed this screen after I posted a video and mentioned problems for a day about update 6.14.1. But they did nothing about having to process a credit card 2 times. I saw nothing on here besides my comment about it so I was thinking it was an isolated problem with MY stands.

Here is the link to my post and another merged post of mine about update 6.14.1:

Known-Issues-on-Update-6-14-1/td-p/652736

Message #8 talks about me having to scan a Credit Card 2 times like you mention. Which as you mention I also have this problem still.

@_Violet :

I know last week I was very vocal to say the least about update 6.14.1 but it seems no one has emailed me about the issues of update 6.14.1, or that the roll back of 6.14.1 was fully done since there are still issues with taking a payment.

Adding items to the cart has been fixed with the roll back but when we press charge, the reader beeps like it took payment, but gets stuck Processing. Then I have to cancel the order, type in the managers pin, which brings me back to the cart. Press Charge, they tap or dip the card. This all only started after the initial release of 6.14.1. I am currently on Square for Retail 6.15 (6150013). Can you ask if this issue is going to be rolled back too? I only tagged you because you seemed to get someone higher to look at this issue last week. Thank you again for doing that.

Re: Authorization On Square Stand Requires 2 attempts.....

SuperiorImages — Mon, 24 Apr 2023 22:23:13 GMT

I am struggling with the same issue this week, I use Square Appointments - every card transaction takes two attempts to process. It doesn't matter if it's a tap or dip, I have to cancel out the first attempt and do it again to complete the process.

It beeps the first time too, which makes you (and the client) think it's working... so Ive been explaining to everyone that I have to do it twice, before we even start the process. Very frustrating.

I have the newest model Square Stand w/iPad.

Re: Authorization On Square Stand Requires 2 attempts.....

MountainHouse — Wed, 26 Apr 2023 21:22:31 GMT

I do not understand why this issue isn't being resolved!!!! issquareup.com continues to state that all systems are operational, and they are not! We are going on a full week of this issue!!!! When using Square For Retail on the Square Stand with an iPad OR Square for Restaurants on Square Stand with iPad, credit card authorization takes two attempts! Tap to pay, google pay or Apple pay causes the readers light to go out and beep, but NOTHING shows up on the screen, you must cancel the sale and start over. Chip cards inserted into the reader cause the screen to get stuck indefinitely on "Preparing Payment". You have to cancel the transaction and have the chip card reinserted. We have the latest version of iPadOS, the latest version of Square for Retail, and square for restaurants. We have hard reset the card reader by holding down the button until the red lights stop, we have hard reset the iPads. Nothing on our end is the cause of this problem. I have called twice now about this, the first agent said she would report it, nothing happened, called again, this agent said he would report it, and said he couldn't see that it was ever reported by me before. I even shared with him the thread about this in the community so he could see others were also affected. Nobody has called back, nobody has messaged, the problem hasn't been fixed. WHAT IS GOING ON SQUARE???? Customers are extremely annoyed by this issue as they think they are being charged twice! Particularly when they use their phone to tap, as their phone screen registers that the payment went through on the first try. Would somebody PLEASE acknowledge this issue and do something to fix it!!!

Re: Authorization On Square Stand Requires 2 attempts.....

Candlestore — Thu, 27 Apr 2023 13:11:30 GMT

@MayaP ;

Any Idea how to get this to the Update Team since they think their Roll back of 6.14.1 update has fixed this issue?

It is still present or came back in Update 6.15 (6150013) on my Square Stand running the newest updated version of IOS.

Tagged you since no one from Square has acknowledged this problem is still going on here from this article or from my original post of Known issues with 6.14.1 that has been marked as Solved. Which is why I believe this issue is not getting fixed.

Re: Authorization On Square Stand Requires 2 attempts.....

MayaP — Fri, 28 Apr 2023 13:40:16 GMT

Thanks for checking in on this @Candlestore . I did speak with our team and they did re-open the ticket and it is currently being worked on by the engineers. I am sorry this has been such a mess, but I am hoping our team will address it once and for all!

As soon as there are any updates I will let you know.

Card reader not working. It beeps once they tap their card but payment doesn't actually go through

Hello-PS-SF — Sat, 29 Apr 2023 23:53:26 GMT

When customers use their contactless card or Apple Pay to tap, the reader makes its regular beeping noise to show completion, but the transaction doesn't actually go through/process on the ipad. So we have to "cancel," press "charge" again, and ask the customer to try again and then it works and payment finally goes through.

This has been happening for a few weeks now. We even bought a new card reader and new ipad and we're still having this issue. 😞 We charged the reader, reset it, and unlinked/linked. We've been updating the square app too.

Can anyone help? Anyone else having this problem? This is extremely frustrating for customers. @Square

Re: Authorization On Square Stand Requires 2 attempts.....

MountainHouse — Sun, 30 Apr 2023 03:56:59 GMT

Have you heard anything or been contacted? Absolutely nothing here and the problem persists.

Today we noticed a rapid reconnect to the reader yellow message bar after hitting charge for more than half of our transactions today. Both on square for retail and restaurants.

Re: Authorization On Square Stand Requires 2 attempts.....

_Violet — Mon, 01 May 2023 21:42:52 GMT

Hi there, @MountainHouse @Candlestore @SuperiorImages @Hello-PS-SF and any others who may be experiencing this issue.

If you haven't already, please reach out to our Support Team directly by logging into your Square account and heading here. Although I am happy to help if and when I can, these types of technical issues are owned by our Support Team until resolution. They can add you to a support ticket and watch for updates on it from our engineering team on the ticket itself. Along the way, the support advocate(s) you are working with should be providing you with any significant updates they receive.

Rest assured, our engineers are aware of this issue and are currently working towards a solution. I do apologize for the inconvenience, as I realize this is disruptive to your checkout flow 😓 I'll let you know if I get word of this issue being resolved. We appreciate your patience and understanding in the meantime 🙏

Re: Authorization On Square Stand Requires 2 attempts.....

Hello-PS-SF — Mon, 01 May 2023 21:55:21 GMT

Thank you for responding and letting us know this! I will contact Support Team.

Re: Authorization On Square Stand Requires 2 attempts.....

_Violet — Mon, 01 May 2023 21:59:10 GMT

You're welcome, @Hello-PS-SF ~!

Re: Authorization On Square Stand Requires 2 attempts.....

MountainHouse — Tue, 02 May 2023 12:39:55 GMT

Thanks for the update @_Violet , however all of us have called support, myself twice. Nobody follows up, at all. Thursday makes a full 14 days since this issue started for us, and we haven't been informed about anything! I would especially like to know why this issue is taking so long to be fixed, as this is completely out of the norm for Square. I do appreciate your checking in, but could you possibly get some kind of status update or explanation as to why this issue can not be fixed promptly?

Re: Authorization On Square Stand Requires 2 attempts.....

MountainHouse — Tue, 02 May 2023 12:41:43 GMT

Also, the link you provided for Square systems status, has never listed or acknowledged this issue.

Re: Card reader not working. It beeps once they tap their card but payment doesn't actually go throu

MountainHouse — Tue, 02 May 2023 12:44:06 GMT

Many of us are having this issue, and so far Square has not fixed it, calls to customer support are fruitless as they say we will be contacted about it and nothing ever comes of it. Maybe if more people call they will take this seriously???

Re: Authorization On Square Stand Requires 2 attempts.....

Candlestore — Tue, 02 May 2023 13:24:33 GMT

@MountainHouse @_Violet @Hello-PS-SF @MayaP @SuperiorImages ;

The tech department has never emailed about this issue or other issues, BUT I did get an tag or notice from these Forums that Square thinks they have seen that the Issue is with the Square Reader. So I replied back since I have 4 of the Tap to Pay readers, I switched the one I normally use out and connected one of my Backups, Still same issue. I do remember seeing an update pop up for my reader and which was separate from the Stands Update. I just do not know how to tell which version my Reader has or was on. Besides this issue I am trying to fix my Sales tax issue.

Somehow within the Last month my items that are not to have Sales tax started having sales Tax show up, these were setup in 2019 with no Tax and worked Fine till a month ago. And Squares Support answer is not working for me since I have 6000 plus Items and about 30 do not get sales tax applied. I use to toggle Sales Tax on or off on the Item itself online, this button is gone, or Check N in column V of the csv file of my Catalog... Which that Column is also gone now.

Troubleshooting/What-Happened-to-the-Sales-tax-Y-N-in-my-Catalog-export/td-p/655930

Even Squares online help for this tells you you can use the Catalog Import Tool.... which You cant

5061-create-and-manage-your-tax-settings#:~:text=From%20the%20Square%20app%2C%20tap,tax%20rates%20on%20or%20off.

I am trying to run a business not trouble shoot and fix issues Square Creates.

Re: Authorization On Square Stand Requires 2 attempts.....

MountainHouse — Tue, 02 May 2023 14:03:14 GMT

We have also had sales tax randomly turn itself on for non-taxed items over the years.. I've never reported it, we just fix it as we go... 😞

Re: Authorization On Square Stand Requires 2 attempts.....

Candlestore — Tue, 02 May 2023 14:50:46 GMT

@MountainHouse ;

Yea me too, and then I could search for the item in my catalog Toggle Sales Tax On/Off and save in the dashboard or through the catalog.csv file. Now Squares Idea (FROM CALLING SUPPORT) is that if I add a new Item that does not have Sales Tax, I add the item, then go to Settings - Business- Sales Tax, Select Tax ON for ALL (6000 plus items) then Search for Each Item I need to turn Tax off for. That is the Stupidest thing I have heard of!! But wait there is more, When I select to turn on sales Tax for ALL items not All get turned ON, as I looked for the 30 I need to turn off, a lot were not turned ON!! See my link to the Trouble Shooting post from before in this thread, out of 6000 plus items 254 end up having sales tax turned on after i was trying to fix this yesterday. So currently, for me to have the most items with the correct tax settings, I have all items requiring Sales Tax, and need to turn off the sales tax manually when an item not requiring Sales tax is scanned in during the processing of a Sale. Maybe it is because I have so many Items but I know other sellers with more.

Unless you have an idea for me to do this, I am all eyes on the screen for them :).

You may want to look at how your turned Tax on and off and see if you can still do it that way. I am going through the Dashboard so it's not an Update to My Square Stand that is missing, this is Squares Dashboard settings and their Back Office changes. I even asked the Beta team I am testing in to see if this Tax issue could be related. Nope according to the Beta Team.

Square basically Broke something that was easy to fix to something almost impossible to fix and changed my Tax settings unknowingly to me with an 'Update?"

Sorry just frustrated between The Reader issues now to learn about this.

Re: Authorization On Square Stand Requires 2 attempts.....

MountainHouse — Tue, 02 May 2023 15:15:55 GMT

Wow! That sounds terrible! Luckily we haven’t had it that bad. But to your point I wish square would lay off all the cosmetic changes that they keep doing and focus on stability.

Re: Authorization On Square Stand Requires 2 attempts.....

mumsflowers — Tue, 02 May 2023 22:29:41 GMT

We are also having the same issue ever since the we updated our retail app for square - the transaction has to be reset after the first attempt for the customer to pay successfully. Super awkward and frustrating for a business! We have uninstalled and reinstalled square, bought a new chip reader, unplugged everything and reset all out hardware, etc. the only thing I can do to make it seem seamless for our customer is to hit the payment button, quickly exit out of it and hit the payment button again before indicating it is ready for payment. Extremely inconvenient for a business to operate with no foreseeable end in sight!

Re: Authorization On Square Stand Requires 2 attempts.....

MountainHouse — Tue, 02 May 2023 22:49:49 GMT

If you haven’t called tech support please do. We need to get them to do something about this. It’s been 2 weeks now with no resolution.