If you can, try connecting to your phone's hotspot to get past the software update. The 14.40 error is often caused by special characters in the Wi-Fi password, so eliminating them is another option and maybe the only option if the software update doesn't get you going.
Roku Community Streaming Expert
Help others find this answer and click "Accept as Solution."
If you appreciate my answer, maybe give me a Kudo.
I am not a Roku employee.