Failure to report bad news at the right time has been one of the major contributors to IS project failures. While prior studies have identified many factors that can affect bad news reporting, there is a dearth of research on how context and timing affect the perception and reporting of bad news. Furthermore, little is known about how individuals perceive and process different types of bad news that can emerge during a project’s lifecycle. In this study, we employ a multiple case study approach to address these important theoretical gaps that exist within the bad news reporting literature. Our aim to shed light on how context and timing affect bad news reporting in IS projects.