As part of the Community and Environment in Rural America (CERA) initiative, the Carsey Institute has been investigating broad trends between rural community types, including the education level of residents and their parents. Since 2007, Carsey researchers have conducted over 17,000 telephone surveys with randomly selected adult Americans from twelve diverse rural locations to ask about both their own and their parents' educational attainment, as well as their perceptions of school quality in their communities. Survey results conclude that educational achievement varies significantly by type of place in rural America. In chronically poor rural areas, 45 percent of residents have completed only high school or less, compared with 22 to 33 percent in amenity-rich, amenity-transition, and declining resource-dependent rural areas. Although people from all types of rural communities generally have more education than their parents, those in chronically poor rural areas still have relatively low education levels--a disadvantage that persists across generations. This brief highlights the need to invest in the educational systems of chronically poor rural areas where generations of underinvestment have contributed to persistent poverty. (Contains 3 figures and 8 endnotes.) [This work was supported by the Neil and Louise Tillotson Foundation.]