After 1997 the district educated students at
Saint Basil Academy in
Garrison after that institution stopped in-house instruction. In 2003, Highland Falls-Fort Montgomery stopped allowing St. Basil students to attend classes at Highland Falls-Fort Montgomery because St. Basil was not paying tuition for the students. Saint Basil had failed to pay $237,000 to HFFMCSD. In 2004 the
New York State Education Department decided that in the meantime, the
Garrison Union Free School District (which sends high school students to Highland Falls-Fort Montgomery) would be the school district for Saint Basil Academy students who originated from households residing in New York State, although the Garrison district operated in a manner that the order did not require them to pay for the education of high school students. Frank Sheboy began his term as superintendent circa 2015. In 2021 the agency at West Point announced that the bid to educate West Point High School students would be competitive. In 2022 Sheboy decided to leave his position. ==Service area==