One of the most perplexing issues facing the enterprise handheld mobile device market today is the variety of operating system (OS) options. In the past, Windows CE/Mobile handhelds were the clear choice with little to no competition outside of homegrown systems. Now, three operating systems have emerged on the market: Windows 10 IOT mobile, Android and iOS. So, where do we go from here? Throughout this piece, benefits and challenges will be highlighted for each OS option.