This is an analytical report that looks across four district case studies (published between 2007 and 2009 by the Small Schools Project) to reflect on what happens when a district commits to the goal of graduating each student ready for college, career, and citizenship. The report describes four challenge areas--differentiation and standardization, capacity building, equity and resources, and use of data--that highlight the need for greater connection, alignment, and capacity throughout the district system if they are to reach this college-ready goal. (Four appendixes are included: (1) Cascades School District; (2) Olympic School District; (3) Forest Hills School District; and (4) Eastridge School District. Contains 24 notes.)