Software upgrades play a pivotal role in enhancing software performance, and are a critical component of resolving software bugs and patching security issues. However, consumers' eagerness to upgrade to the newest operating system is often tempered after release. In this paper, we focus on the upgrade perceptions and practices of users utilizing Microsoft Windows, with particular consideration given to the current upgrade cycle to Windows 10, which was, for a time, offered at no monetary cost to many users. To better understand the relevant factors for upgrade decisions, we deployed a structured survey, including several open-ended questions to add additional depth. We collected data from 239 Microsoft Windows users and utilized qualitative and quantitative methods to analyze user upgrade practices. Important themes include how to best notify users of upcoming upgrade opportunities, how users perceive privacy issues associated with OS upgrade decisions, and whether security constitutes a significant decision-making factor. We also explore how end-of-life dates, indicating the end of support by the vendor, are perceived by users.