Leaked passwords from data breaches can pose a serious threat if users reuse or slightly modify the passwords for other services. With more and more online services getting breached today, there is still a lack of large-scale quantitative understanding of the risks of password reuse and modification. In this project, we perform the first large-scale empirical analysis of password reuse and modification patterns using a ground-truth dataset of 28.8 million users and their 61.5 million passwords in 107 services over 8 years. We find that password reuse and modification is a very common behavior (observed on 52% of the users). More surprisingly, sensitive online services such as shopping websites and email services received the most reused and modified passwords. We also observe that users would still reuse the already-leaked passwords for other online services for years after the initial data breach. Finally, to quantify the security risks, we develop a new training-based guessing algorithm. Extensive evaluations show that more than 16 million password pairs (30% of the modified passwords and all the reused passwords) can be cracked within just 10 guesses. We argue that more proactive mechanisms are needed to protect user accounts after major data breaches. / Master of Science