Background/Context: Early warning indicators (EWI) are often used by states and districts to identify students who are not on track to finish high school, and provide supports/interventions to increase the odds the student will graduate. While EWI are diverse in terms of the academic behaviors they capture, research suggests that indicators like course failures, chronic absenteeism, and suspensions can help identify students in need of additional supports. In parallel with the expansion of administrative data that have made early versions of EWI possible, new machine learning methods have been developed. These methods are data-driven and often designed to sift through thousands of variables with the purpose of identifying the best predictors of a given outcome. While applications of machine learning techniques to identify students at-risk of high school dropout have obvious appeal, few studies consider the benefits and limitations of applying those models in an EWI context, especially as they relate to questions of fairness and equity. Focus of Study: In this study, we will provide applied examples of how machine learning can be used to support EWI selection. The purpose is to articulate the broad risks and benefits of using machine learning methods to identify students who may be at risk of dropping out. We focus on dropping out given its salience in the EWI literature, but also anticipate generating insights that will be germane to EWI used for a variety of outcomes. Research Design: We explore these issues by using several hypothetical examples of how ML techniques might be used to identify EWI. For example, we show results from decision tree algorithms used to identify predictors of dropout that use simulated data. Conclusions/Recommendations: Generally, we argue that machine learning techniques have several potential benefits in the EWI context. For example, some related methods can help create clear decision rules for which students are a dropout risk, and their predictive accuracy can be higher than for more traditional, regression-based models. At the same time, these methods often require additional statistical and data management expertise to be used appropriately. Further, the black-box nature of machine learning algorithms could invite their users to interpret results through the lens of preexisting biases about students and educational settings.