In spite of novel cybersecurity threats, digital security advice has remained largely unchanged in recent years. In fact, a lot of advice in response to high-profile attacks doesn’t actually address risks people are most likely to face. This talk will analyze several high-profile digital security concerns, whether viral advice to address it would have been effective, and what steps could be taken - both before and after the issue arises. You will hear of lessons learned from years of auditing and updating Security Planner, a digital security guide that provides customized plans based on responses to a few survey questions. The presentation will further delve into ways to segment digital security advice so that it’s personalized to the individual, their devices, their technical capabilities, and the type of risks they’re likely to face.