Software updates are critical to the security of software systems and devices. Yet users often do not install them in a timely manner, leaving their devices open to security exploits. This research explored a re-design of automatic software updates on desktop and mobile devices to improve the uptake of updates through three studies. First using interviews, we studied users’ updating patterns and behaviors on desktop machines in a formative study. Second, we distilled these findings into the design of a low-fi prototype for desktops, and evaluated its efficacy for automating updates by means of a think-aloud study. Third, we investigated individual differences in update automation on Android devices using a large scale survey, and interviews. In this thesis, I present the findings of all three studies and provide evidence for how automatic updates can be better appropriated to fit users on both desktops and mobile devices. Additionally, I provide user interface design suggestions for software updates and outline recommendations for future work to improve the user experience of software updates.