The achievement gap between southeastern Wisconsin schools and those in the rest of the state has widened in all subjects and at all grade levels from 2006. Although school spending is above the state average in the region, and removing the Milwaukee, Racine, and Kenosha public school districts from the equation currently improves overall performance in the region, the trending of smaller urban areas toward stresses similar to those in their large counterparts indicates that soon it will not be possible to improve the numbers by taking the biggest cities out of the equation. These stresses include: (1) Declining enrollment; (2) More minority majority districts; (3) More schools needing improvement; (4) More poverty; (5) Lower graduation rates; and (6) Lower student engagement. (Contains 15 tables.) [Additional funding for this report was provided by by Cardinal Stritch University, Multiple Listing Service, Northwestern Mutual Foundation and Stifel Nicolaus Investment Services.]