Many people delay or completely avoid updating the software on their devices. This can cause serious issues for security and software management. Most computers are compromised using vulnerabilities for which a security update already exists. If users had updated they would have been safe. Despite this many users still choose to not update their devices. The fact is that updating software is risky for end users. In this talk, I will discuss my research exploring the reasons people choose to avoid updating their devices. I will also discuss how these reasons relate to software design and discuss approaches that will likely improve update installation rates.