thread Re: Square Card Readers Not Pairing With Some iPads after IOS 16.6 Update in Payments Troubleshooting

Square Card Readers Not Pairing With Some iPads after IOS 16.6 Update

valas-creator — Sat, 20 Sep 2025 08:47:10 GMT

I have tried working with Square support on this issue and have not gotten any traction. It is not a simple issue to resolve such as forgetting the card reader, factory resetting the iPads, or even rolling back the iPads to IOS 15.X as Apple has unsigned all of the previous releases do to "a security concern."

Here is the issue we are seeing on the iPad 9th Gen running IOS 16.6:

We are unable to pair the card reader to the Square POS standard and the Square Restaurant App. The applications see the card reader and when we set up pairing the black box with a white circle spins until it times out with an error, "Failed to Pair Point of Sale Failed to pair with your Square Reader for Contactless and chip. Please try pairing again. The Pair your Reader function lists the correct "Contactless and Chip (8560)" reader under select a reader.

What we know: 1. These ipads worked before the upgrade to IOS 16.6.

2. Apple support states that the issue is on the 3rd party application.

3. The application does not prompt IOS to pop up the modal box asking if it is alright to pair with the device.

4. The card reader pairs on iPads running IOS 15.6.1 with no issue receiving the ask if it is alright to pair.

What we have tried 1. resetting the card reader.

2. purchasing a new card reader

3. resetting the iPad network

4. Factory resetting the iPad

5. Rolling back the IOS upgrade from 16.6 back to 15.6.1 (Apple will not allow through iTunes)

6. Calling Apple Support and begging them to roll back but they said no can do.

7. Apple support telling us it must be on the 3rd party apps end even though the modal box is IOS.

8. Reaching out to our Square Rep and Square phone support.

9. Square phone support passed us up the chain after their troubleshooting did not work.

10. Square engineers keep asking us to do the above. We have been sending video proof of the issue not being corrected by the usual troubleshooting.

I am attaching a picture of the modal message we should be getting but are not on the 9th Gen iPad running 16.6

Any help would be appreciated at this point as we are reduced to swiping cards on most POS until this is resolved.

Re: Square Card Readers Not Pairing With Some iPads after IOS 16.6 Update

MJD — Tue, 05 Sep 2023 19:22:15 GMT

Hey @valas-creator!

This situation seems less than ideal 😔. Have you tried connecting to the reader through your Bluetooth settings in iPadOS settings? Have you had any luck connecting to any up-to-date iPhones as these run on iOS rather than iPadOS?

Also tagging in @isabelle to see if there are any known issues with connectivity of readers at the moment.

If this did help, please mark it as best answer to help others in the future!

Re: Square Card Readers Not Pairing With Some iPads after IOS 16.6 Update

valas-creator — Wed, 06 Sep 2023 19:21:29 GMT

Thank you for the reply.

We are able to connect other Bluetooth devices to the 9th gen Ipads running IOS 16.6 upgraded from 15.6.1.

We are able to connect the card reader to an iPhone 11 Pro running IOS 16.6 as well as a 6th gen iPad running IOS 16.6 after a factory reset. The Square Standard POS application did crash on the IPhone during the initial pairing attempt but was ultimately successful.

Re: Square Card Readers Not Pairing With Some iPads after IOS 16.6 Update

valas-creator — Wed, 20 Sep 2023 16:02:53 GMT

We had hoped that IOS 17 would fix the issue but this is not the case. We have purchased Square Stand V2 for each iPad with the issue and this resolves the issue by directly connecting the card readers through USB instead of Bluetooth.