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Troubleshooting a Bluetooth Square Reader in the Trail’s End App®

If your Bluetooth Square Reader will not connect to the Trail’s End App®, use the steps below to troubleshoot the connection.

Written by Rachelle C

✅ Note: If you are unable to use a Square Reader, you can still accept credit cards by manually entering card information in the Trail’s End App®.

Tap to Pay Troubleshooting

If Tap to Pay is not working, please review the platform-specific guides:

Important: Pair the Square Reader from inside the Trail’s End App®. Do not pair it directly from your phone or tablet's Bluetooth settings.

Before You Start

Make sure:

  • Your Square Reader is charged.

  • Bluetooth is turned on.

  • Your phone or tablet is connected to the internet.

  • The Trail’s End App® is updated to the latest version.

  • The reader is within 10 feet of your phone or tablet.

  • The Trail’s End App® has permission to use Bluetooth or Nearby Devices.

Square requires an internet connection when setting up a reader so it can authenticate the reader and check for firmware updates.

1. Put the Square Reader Into Pairing Mode

  1. Open the Trail’s End App® and go to Settings > Square Settings.

  2. Select the option to connect a Square Reader.

  3. Press and hold the button on the Square Reader for approximately 3–5 seconds.

  4. Release the button as soon as the orange lights begin flashing.

The lights indicate what the reader is doing:

Lights

Meaning

Four flashing orange lights

Reader is ready to pair

Four green lights

Reader paired successfully

Four red lights

Pairing failed

If the lights turn red while you are holding the button, you held the button too long. Release it and try again.

2. Accept Any Bluetooth Pairing Requests

Your phone or tablet may display a Bluetooth pairing request after the reader is discovered. Tap Pair when prompted.

On some Android devices, you may receive multiple Pair or Pair & connect prompts. Accept each prompt immediately. Square recommends responding to these prompts within about five seconds or the pairing attempt may fail.

When pairing is successful, the reader should appear as Ready in the Trail’s End App®.

3. Restart Bluetooth

If the reader does not appear or pairing fails:

  1. Open your phone or tablet's Settings.

  2. Turn Bluetooth OFF.

  3. Wait a few seconds.

  4. Turn Bluetooth ON again.

  5. Return to the Trail’s End App® and try pairing again.

Do not select the Square Reader from the phone's Bluetooth device list. Start the pairing process from inside the Trail’s End App®.

4. Remove an Existing Reader Connection

If the Square Reader has previously been connected to this phone or tablet, an old Bluetooth connection may interfere with pairing.

If the reader appears in your phone's Bluetooth settings:

  1. Open Settings > Bluetooth.

  2. Find the Square Reader.

  3. Select Forget, Unpair, or Remove Device.

If the reader is already listed inside the Trail’s End App®, remove or forget the reader there as well.

Then restart Bluetooth and try pairing again.

If the reader has never connected to the device, it may not appear in the Bluetooth device list. In that case, simply continue to the next step.

5. Restart the Square Reader

If the reader still will not pair, restart it.

  1. Charge the reader for at least 20 minutes.

  2. Press and hold the button on the reader for approximately 20 seconds.

  3. Continue holding the button until the red lights have finished flashing.

  4. Release the button.

  5. Press the button once to turn the reader back on.

  6. Try pairing again using the normal 3–5 second pairing process.

Restarting the reader does not affect Trail’s End sales or payment history.

6. Try Another Phone or Tablet

If possible, try connecting the Square Reader to the Trail’s End App® on another compatible phone or tablet.

This can help determine whether the problem is with:

  • the original phone or tablet,

  • its Bluetooth connection or permissions,

  • or the Square Reader itself.

If the reader fails in exactly the same way on multiple devices, the reader itself becomes a more likely cause.

7. Test the Reader With the Square App

If the Square Reader still cannot connect, testing it with Square's own Point of Sale app can help isolate the problem.

Have the owner of the Square account attempt to connect the reader through the Square Point of Sale app.

  • If the reader connects successfully to Square but not Trail’s End: contact Trail’s End Support so we can investigate the Trail’s End App® connection.

  • If the reader also fails to connect to the Square app: the issue is more likely related to the reader, its Bluetooth connection, firmware, or hardware.

Android: Clear the Bluetooth Cache

If you're using an Android device and other troubleshooting has failed, resetting the phone's Bluetooth data may help.

On supported Samsung devices:

  1. Open Settings > Apps.

  2. Choose the option to Show system apps.

  3. Find Bluetooth.

  4. Select Storage.

  5. Clear the Bluetooth data/cache.

  6. Restart the phone.

Note: Clearing Bluetooth data may remove other Bluetooth connections from your phone, requiring you to reconnect devices such as headphones, watches, or your vehicle.

Square specifically recommends clearing Bluetooth data/cache as an advanced troubleshooting step on supported Android devices.

Still Having Trouble?

Contact Trail’s End Support and include:

  • Your phone or tablet model

  • Your operating system version

  • Whether the reader appears in the Trail’s End App®

  • What lights appear on the reader when you attempt to pair

  • Whether you've tried another phone or tablet

  • Whether the reader can connect using the Square Point of Sale app

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

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