Bose Soundsport Free Wireless - Not Connecting or No sound on Left bud - Windows 10 - Aug 2019
I had the same issue, first not being able to connect my headphones, later when I could, the sound only came from the right bud.
I some cases I got to make them both work but after disconnecting and reconnecting I had the same issue again.
After testing several methods I got them working with any further issues.
Here are the steps I followed for a steady solution:
1.- Update your Windows 10 Version, windows had a problem with the driver that recognized the headphones as a Voice only device, it should be Voice and Music, to make both buds play.
To download the latest version just type "Windows Update" on the search menu, then check the updates.
Update to version 1903 or a later version, they fixed a bug on the sound driver, several devices reported the same issue.
2.- Make sure you have the latest update on your Bose headphones.
Use this Link from bose to update them: https://btu.bose.com/#section=start
I had them on version 2.5.4, it was updated to 2.6.0
3.- If you had previously paired your device remove it. We want to start at 0
4.- Press the left bud button for 10 seconds until you hear “Bluetooth device list cleared”
5.- (Key Point) The system recognizes a second Bluetooth device with the prefix "LE-" make sure you connect/pair this one first before our headphones.
6. Once our "LE-" device is paired, pair your headphones. It's easy to identify the difference due to the icon.
After this, you should see your device connected with the legend "Connected voice, music".
I haven't had the same issue again and now they work perfectly, even the sound is better with the latest update.
Have fun! Enjoy your headphones!