I purchased a cheap USB to serial adapter off of eBay.
This particular adapter uses the Prolific 2303HX chipset, which is not supported by windows 8 or newer according to the Prolific website.
It appears to work fine on Linux.
When connected a Windows 8 or newer box, it show up in Device Manager with the error “This Device cannot start. (Code 10)”.
To fix the issue, replace the windows default driver using the one below. It is version 3.3.2 with a date 9/24/2008.
Driver Download: Profilic_Win8_x64_x86