The Colorado Department of Education recently received state funding to implement a Student Re-Engagement Grant Program (SRGP). The goal of this project is to inform the administration of the SRGP by looking back at data from a previously administered grant program, called Colorado Graduation Pathways (CGP). The CGP program was a federally funded grant with similar objectives to the SRGP (e.g., decreasing the dropout rate; increasing the high school graduation rate). Student-level data from one year of this program were used in combination with state administrative data to describe the relationships between targeted interventions and educational outcomes for served students, such as staying in school and graduating from high school. This was not a causal study -- that might suggest that outcomes were a result of specific interventions. Instead, the descriptive exploratory nature of the analyses is best used to generate ideas and guide conversations about strategic grant-making. The findings from the study suggest considering: (1) engaging grantees in conversations about equity and access; (2) expanding investments to create continuity through school transitions for all grade levels; (3) targeting interventions and supports to students who change schools during 12th grade so that they are more likely to graduate; (4) sustaining or increasing investments in Check & Connect to help keep students in school; (5) accelerating investments in Title I and highly mobile students; and (6) requiring grantees to report program data at the student level.