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Troubleshooting a USB-C Square Reader in the Trail’s End App®

If your USB-C Square Reader is not working with the Trail’s End App®, use the steps below to troubleshoot the connection.

Written by Brian Deyo

The USB-C Square Reader for magstripe plugs directly into your phone or tablet. It does not pair through Bluetooth.

Important: The USB-C reader only accepts cards by swiping the magnetic stripe. It does not support chip or contactless tap payments.

Before You Start

Make sure:

  • You are using the USB-C version of the Square Reader for magstripe.

  • Your phone or tablet has a USB-C port.

  • Your device is compatible with the Square Reader.

  • Your device software and the Trail’s End App® are updated.

  • The USB-C port is clean and free of debris.

Square currently lists the USB-C Square Reader for magstripe as compatible with supported Apple and Android devices running at least iOS 15 or Android 9.

1. Plug the Reader Directly Into Your Device

  1. Open the Trail’s End App®.

  2. Insert the USB-C Square Reader firmly into your phone or tablet's USB-C port.

  3. Make sure the reader is inserted completely.

There is no Bluetooth pairing process for this reader. The Trail’s End App® should detect it automatically when it is connected.

2. Remove Your Phone or Tablet Case

Some protective cases prevent the reader from inserting completely into the USB-C port.

Even if the reader looks connected, a small gap can prevent the phone from recognizing it.

  1. Remove your device case.

  2. Unplug the Square Reader.

  3. Plug it directly into the device again.

  4. Return to the Trail’s End App® and try taking a payment.

Square specifically recommends removing protective cases when troubleshooting a magstripe reader connection.

3. Disconnect and Reconnect the Reader

If the reader is not detected:

  1. Completely unplug the Square Reader.

  2. Wait a few seconds.

  3. Plug it firmly back into the USB-C port.

  4. Close and reopen the Trail’s End App® if necessary.

Also try turning Bluetooth off and back on. Although the USB-C reader itself does not use Bluetooth, Square includes resetting Bluetooth among its troubleshooting steps for magstripe-reader connection problems.

4. Check the USB-C Port

Confirm that the phone's USB-C port is working correctly.

Try connecting another USB-C accessory or charger.

If other accessories are also unreliable:

  • Inspect the port for lint or debris.

  • Make sure the connector seats completely.

  • Try another compatible phone or tablet if available.

A damaged or obstructed USB-C port can prevent the reader from being detected.

5. Avoid USB-C Adapters or Extensions

Whenever possible, connect the USB-C Square Reader directly to the phone or tablet.

Adapters, extension cables, hubs, or USB converters can interfere with the connection. Square does not guarantee compatibility with most third-party adapters.

6. If You're Using an iPhone or iPad

Some Apple devices may ask you to identify a USB accessory when it is first connected.

If prompted to identify the reader as an audio accessory, select Headphones.

If Other Device was accidentally selected, Square recommends:

  1. Unplugging the reader.

  2. Open Settings.

  3. Go to Sounds & Haptics > Headphone Safety > USB Audio Accessories.

  4. Select Forget All USB Audio Accessories.

  5. Return to the Trail’s End App®.

  6. Reconnect the reader and select Headphones when prompted.

7. Try Another Phone or Tablet

If possible, plug the reader into another compatible USB-C device with the Trail’s End App® installed.

This is one of the quickest ways to isolate the problem.

  • Works on another device: The issue is likely with the original device, USB-C port, permissions, or software.

  • Does not work on either device: The Square Reader itself becomes the more likely cause.

8. Test the Reader With the Square App

If the reader still is not recognized, test it using Square's own Point of Sale app.

Plug the reader into a compatible phone or tablet and attempt to use it with Square Point of Sale.

  • Works in Square but not Trail’s End: Contact Trail’s End Support so we can investigate the Trail’s End App® connection.

  • Does not work in Square either: The problem is more likely the reader, device compatibility, or USB-C connection.

Reader Connected but Card Won't Swipe

If the reader is recognized but a card will not process:

  1. Make sure the card's magnetic stripe faces away from the Square logo, toward the thicker portion of the reader.

  2. Keep the card flat against the bottom of the reader.

  3. Swipe smoothly and consistently through the entire reader.

  4. Try swiping in the opposite direction.

  5. Try a different card.

A damaged magnetic stripe can prevent an otherwise working reader from reading the card.

Chip Cards and Contactless Cards

The USB-C Square Reader for magstripe is a swipe-only reader.

It does not:

  • read EMV chips,

  • accept contactless card taps,

  • accept Apple Pay or Google Pay directly.

Customers must swipe a card with a magnetic stripe.

If you need chip and contactless payments, use a compatible Square Reader for contactless and chip instead.

Still Having Trouble?

Contact Trail’s End Support and include:

  • Your phone or tablet model

  • Your operating system version

  • Whether the reader is plugged directly into the device

  • Whether you've removed the device case

  • Whether other USB-C accessories work with the device

  • Whether you've tried another phone or tablet

  • Whether the reader works in the Square Point of Sale app

These details will help us determine whether the issue is with the reader, the phone or tablet, or the Trail’s End App®.

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