thread Re: Square reader keeps disconnecting from Squarespace in Payments Troubleshooting

Square reader keeps disconnecting from Squarespace

abstractbyrabra — Sat, 20 Sep 2025 18:39:16 GMT

Hi! I have a square reader (2nd gen chip) -- that I've used 4 times. First time worked great and keeps going downhill. It'll say it's connected, sometimes even identify itself when I click that in Squarespace and it won't take a payment.

I've gone through the whole trouble shooting rigamarole and factory reset didn't help.

I need a way to take payments that ideally tracks inventory. This needs to be on my ipad at least for the main part.

I have reached out to square support as squarespace says this is a square issue I need to reach out about... but any help, suggestions?

Thanksss

Re: Square reader keeps disconnecting from Squarespace

VanKalkerFarms — Tue, 20 May 2025 15:27:43 GMT

while investigating your question is the first time I learned Squarespace make a POS system. While I don't have anything to add, I would assume it is just a bluetooth connection, so I am not sure where the issue would be. Hopefully someone else has some experience to help you.

Re: Square reader keeps disconnecting from Squarespace

JJ_ — Tue, 20 May 2025 21:44:38 GMT

Hello, @abstractbyrabra, and welcome to the Square Community 👋

I see that you mentioned doing the troubleshooting steps on the Square Reader (thank you for sharing these details), but have you completed any troubleshooting on your iPad or compatible device? I recommend doing that as well to discard any possible "hiccups" or glitches with your device's Bluetooth.

Here's how to reset Bluetooth on your iPad:

IMPORTANT: This will reset all network settings, including Wi-Fi and Bluetooth, so make sure to have your WiFi password handy to reconnect to your network if required.

Reset Network Settings:

Open Settings > General > Transfer or Reset iPad.
Tap Reset > Reset Network Settings.
Confirm the reset by entering your iPad's passcode if prompted.

Let me know if this helps.

Re: Square reader keeps disconnecting from Squarespace

abstractbyrabra — Sun, 25 May 2025 03:25:41 GMT

Thanks JJ! I am away from the square reader - but I'll try that when I get back. I am not the only person that I've seen this happen to -- I had someone reply on Reddit and they had used this for much longer than me and the issue started around the same time.

Was there an update or something that could be causing this issue?

Re: Square reader keeps disconnecting from Squarespace

JJ_ — Tue, 27 May 2025 16:40:41 GMT

While you're right that this isn't the first time I've heard of something like this happening, I have learned in my time at Square that every report or issue has its nuances.

I will keep an eye out here. Hopefully, the iPad Restore/Reset solves your situation.

Re: Square reader keeps disconnecting from Squarespace

abstractbyrabra — Sat, 31 May 2025 22:00:28 GMT

I finally got around the trying the fix and it disconnected again within 30 minutes and is not reconnecting. So it seems like it is not bluetooth

Re: Square reader keeps disconnecting from Squarespace

sheanewstudio — Thu, 12 Jun 2025 16:28:54 GMT

I am having a similar issue. I thought maybe it was because my square reader was old (1st generation) I replaced it and same issue with the brand new, second generation reader. Using it to run squarespace on my iPad air for in person sales to track inventory.

Re: Square reader keeps disconnecting from Squarespace

abstractbyrabra — Thu, 12 Jun 2025 16:55:18 GMT

Ya... its pretty frustrating -- i am able to still use my magsafe thankfully - but that excludes tap.

Re: Square reader keeps disconnecting from Squarespace

abstractbyrabra — Thu, 12 Jun 2025 16:56:32 GMT

Also i reached out to Squarespace and they told me it was a square issue

Re: Square reader keeps disconnecting from Squarespace

sheanewstudio — Thu, 12 Jun 2025 19:07:55 GMT

Squarespace today did say this is a known issue and their engineering team is working on it.

"After investigating this issue further, and reviewing the device and software details provided, I can confirm that we’re currently investigating an issue with Squarespace Point of Sale where some users utilizing iPad devices upgraded to iOS 18.4+ are experiencing connectivity issues between the Squarespace app and Square readers"

Re: Square reader keeps disconnecting from Squarespace

abstractbyrabra — Thu, 12 Jun 2025 19:12:05 GMT

THAT IS AMAZING -- um can you reply to them and ask how others can submit issues about it? if it needs to be just a case or something specific? Because Squarespace told me to contact square.

Re: Square reader keeps disconnecting from Squarespace

abstractbyrabra — Thu, 12 Jun 2025 19:17:35 GMT

I ended up responding my support ticket on squarespace and shared the link to this chat.

Re: Square reader keeps disconnecting from Squarespace

sheanewstudio — Thu, 12 Jun 2025 19:26:49 GMT

I started by chatting them, then they took it to email

customercare@squarespace.com

I was talking to Savannah J.

Re: Square reader keeps disconnecting from Squarespace

Revivestudio — Tue, 23 Dec 2025 05:12:28 GMT

I have been with square for over 20 years and this I truly the first time I’ve had such a frustrating issue. I have contacted support without any solution. So I had to replace my square chip reader because it kept disconnecting from my network and the new one is doing it also. It’s the holidays and I have tried all of the resets, troubleshooting, settings and it’s still a piece of crap. I need someone to please help figure this out .