Jackson receives and writes many letters detailing the general conditions of Augusta County as he begins his tenure as the local Bureau administrator. Several letters address the state of local freedmen schools, including attempts to begin new schools in the area, and the lack of food and clothing to distribute to the local freedmen. Jackson also deals with a wide variety of legal matters such as contracts, monetary disputes, labor disputes, and the registration of marriages among the ex-slaves.

Jackson reports that local whites have become more comfortable and tolerant of the new rights of the freedmen, in part because the great demand for labor means they need to treat the freedmen well. Active in cases where freedmen are involved, Jackson reports that the courts give African Americans fair and impartial trials. In all Jackson is optimistic, though he expects more trouble to crop up when winter comes. He deals with various legal matters and labor disputes, and continues to work with the local freedmen schools. Jackson also reports the beatings of local freedmen and forwards statements from people who claim to have aided Union soldiers during the war and want compensation. Many freedmen send letters to the Bureau asking for aid in finding family that had been sold away during slavery.

Jackson describes the increase in assaults on black women and complains about the ease with which whites defraud blacks because of the freedmen's lack of education. J. Marshall McCue, for example, writes to Jackson that a conman has been selling false land titles to local blacks. Many of the letters Jackson writes and receives during this period concern freedmen's attempts to local loved ones, the establishment and upkeep of freedmen's schools, and ongoing labor disputes. Jackson discusses efforts to care for poor blacks and their future in Augusta County. Bureau administrators continue to chastise Jackson for filing his reports and requests late.

Many of Jackson's letters during this period relate to efforts to bring new teachers to Staunton for the freedmen schools, since most of the teachers from the previous season did not return, and controversy over a school in the Methodist Episcopal church in Staunton. Jackson also writes about local political conditions and efforts among whites to control black voting. He cites increases tensions between the races, reports several cases of assault against blacks, and details the increased frustration of local African Americans. Jackson continues to receive and forward information about freedmen who are looking for loved ones sold away during slavery, as well as deal with various legal and labor disputes.

Jackson reports on the poor attitudes of local whites and their hostility toward African Americans in Augusta County. Much of Jackson's communication deals with locating displaced family members of local freedmen, and in some cases arranging transportation for reuniting. He reports on several court cases concerning assaults against blacks, and Jackson continues to field a variety of labor and legal disputes. A new school in Augusta writes Jackson for aid, and many letters deal with black schools. Jackson is generally more pessimistic about local conditions and contrasts the sobriety of the freedmen during the Christmas holidays with the drunkeness of area whites.

Jackson continues his work in locating African Americans who had been separated from one another because of slavery, and his work setting up local schools. There is a report by another Bureau agent on assaults against Augusta blacks, lamenting their frequency and the lack of justice in Augusta's courts. Jackson's superior writes a report stating that labor demands in the Shenandoah currently outstrip supply. Jackson deals with various legal and labor disputes, and writes that he does not believe whites and blacks will ever be able to coexist as equals. Several letters deal with Jackson's transfer out of Augusta.