The Hattiesburg Public School District (HPSD) is a small urban school system located in southern Mississippi. Of the almost 4,500 students enrolled in its nine schools, 92 percent are African American and 90 percent receive free or reduced lunch. Currently, HPSD employs 34 administrators, 375 teachers, and 11 technology specialists. When the 21st Century Schools Initiative (21S) began in the 2005-2006 school year, only two of the nine HPSD schools participated--Rowan Elementary and Hattiesburg High School. During the second year of the initiative, however, participation rose to include all of the district's schools, a level that continues to the present. Over time, the 21S vision is helping teachers recognize the value of technology within a 21st century education. In 2008, 83 percent of surveyed teachers agreed that technology was an integral part of their school; by 2009 that number had increased to 92 percent. A large majority of leaders (81 percent) say they have created leadership teams to help support the process of change in their school. The 21S Initiative centers around three structural transformations: (1) Connected District/School; (2) Connected Learning; and (3) Connected Community. Rowan Elementary School Classroom Maps are appended. (Contains 47 figures, 21 tables, and 7 footnotes.)