Problems with Windows 8.1 install of Arduino IDE
Getting started with a new toolchain can be quite a challenge…

I'm not a Windows guy, but it looks like there are drivers that need to  be installed to get things working with the Arduino. I'm guessing that what is going on here is that Windows is looking locally for drivers and not finding them (or any indication that drivers are needed). I think the button was grayed out because it couldn't help – not because help wasn't needed.

Here are a few sources that I found by searching on:


  arduino driver windows 8.1



[SOLVED] Arduino drivers for Windows 8.1 64bit
Windows 8.1 (64bit) USB-serial driver for Arduino?
Installing the Arduino IDE – Windows 8.1 &amp; 10
Install Arduino Drivers on Windows 8


While we're at it, it is worth mentioning that "out of sync" error message from avrdude are very common. A bit of searching here will find you some good resources on solving them as well – deal with the drivers first, then see if errors persist.