Usually when press run, the code will upload and the device will run the program accordingly, but as of recent, I have to reboot the device so it will run the program
Anyone knows a solution to this, or is this device damaged?

I get this from time to time especially when im updating code several times in quick succession, and yeh, I just do a full restart.

If you have issues connecting to the UIFlow Website it may be due to server load as there are alot of people trying to access the server.