thread Re: My Square Reader (Contactless and Chip 4433) will not connect with my IPad. in Hardware Setup & Troubleshooting

My Square Reader (Contactless and Chip 4433) will not connect with my IPad.

AbbyWooProducti — Wed, 08 Oct 2025 17:39:52 GMT

My Square Reader (Contactless and Chip 4433) will not connect with my IPad. I spent one hour on the phone with tech support and tried all of their recommendations including updating the IPad, resetting the reader several times, and i even ordered a new reader and that one will not connect.

Looking for any ideas from the community, all help is welcome.

Re: My Square Reader (Contactless and Chip 4433) will not connect with my IPad.

Sammie_C — Thu, 09 Oct 2025 21:10:25 GMT

Hi @AbbyWooProducti, thank you for your post! I wanted to also welcome you to the Square Community. I am sorry to hear you are having some connection issues.

You may have already gone through this with Support, but could you please answer these few questions:

Could you provide some additional details on what you are seeing exactly on your side? Are you seeing any error messages?
Have you checked that you iPad is up to date?
Are you experiencing the same exact issues with both your old and new Readers? Are there any differences you have noticed?

Feel free to send over these details, and I can take a further look into this for you.

Re: My Square Reader (Contactless and Chip 4433) will not connect with my IPad.

AbbyWooProducti — Sun, 12 Oct 2025 14:53:19 GMT

We did an update on the IPad to the latest version, cleared the square reader to the "Red Lights" several times, and tried numerous other ideas with tech support. I am still getting the "Failed to Pair try paring later" message.

I bougjt the IPad strictly to use with the Square Reader as I am at craft shows and book festivals every weekend since my android phone is unpredictable at best.

Thank you!

Paul T.

Re: My Square Reader (Contactless and Chip 4433) will not connect with my IPad.

Sammie_C — Fri, 17 Oct 2025 23:59:16 GMT

I understand, @AbbyWooProducti. I am sorry for the slow response.

What other troubleshooting did you go over with Support? I just want to make sure when I reach out to our tech support teams I have all the details they may need.

Another quick question, have you tried to connect any other devices to your Square Reader besides the iPad?