While the Court House and many supporting structures have been lovingly preserved over the years, it is the uncertain future of the two old jails. State and local historians and preservationists are concerned about the two structures, and in turn, the integrity and continuity of the court green complex.

Lack of funding and threat of demolition by neglect have dominated the conversation recently as county and town officials struggle to come to some viable agreement about the future of the buildings. Northampton Historic Preservation Society remains an integral part of these conversations as an advocate of protection, stewardship, and feasible solutions. The 1914 Jail, a four-square brick, currently sits vacant. In use until 2000, it was shut down in 2009 after the conclusion of lead and asbestos abatement. In its time, it was considered a large, modern facility "worth a dozen of the dinky little hovels" now in use as a jail. And one which "could handle a good portion of the speak-easy crowd even if they are numerous." The smaller 1907 jail, which sits behind the 1914 building, is a one-story brick structure needing repair though it still retains many of its original architectural elements. (The 1914 Jail was torn down in late 2017, but the 1907 Jail still remains.)