In this work, we investigate the effectiveness of deep-learning-based password guessing models for targeted attacks on human-chosen passwords. In recent years, service providers have increased the level of security of users' passwords. This is done by requiring more complex password generation patterns and by using computationally expensive hash functions. For the attackers this means a reduced number of available guessing attempts, which introduces the necessity to target their guess by exploiting a victim's publicly available information. In this work, we introduce a contextaware password guessing model that better capture attackers' behavior. We demonstrate that knowing a victim's email address is already critical in compromising the associated password and provide an in-depth analysis of the relationship between them. We also show the potential of such models to identify clusters of users based on their password generation behaviour, which can spot fake profiles and populations more vulnerable to context-aware guesses. The code is publicly available at https://github.com/spring-epfl/DCM_sp.