In 2001, Donald Post became the school's second headmaster, and in 2006 moved to the Faith City Family Church building in Christiana.

Under Reach's acquisition of Tall Oaks, athletics and other after-school activities were merged with Red Lion's programs.

[7] DVCS students have the opportunity to earn several college credits before graduation through a dual enrollment program with Cairn University.

[8] There are also elective opportunities for art, chess club, Russian literature, athletics, speech & debate, vocal ensemble, drama, orchestra, and creative writing.

[10] At the 2021 MIL League Championship, girls cross country runners took 2nd and 3rd place overall, but did not have enough participants to qualify for team standings.

[13] During their partnership on the Red Lion campus, Tall Oaks students earned lead roles in productions of the musicals The Wizard of Oz, The Pirates of Penzance, and Newsies.

[20] Seniors present and defend a thesis as a requirement for graduation, after which it can be nominated for submission to the annual ACCS Chrysostom Oratory Competition.

Students Kelly Weber, Phoebe Hu, and Sarah Chaffee represented Tall Oaks by earning first prize in the ACCS Chrysostom Oratory Competition in successive years from 2011–13, and in 2017, Kana Turley became the fourth Tall Oaks student to earn first prize in the competition.

[33] In 2023, the middle school team earned DVCS its first state championship, with 1st place finishes in four events and top 5 in eleven others.

[36] The middle school team repeated as state champions in 2024, with 1st place finishes in six of the twenty-five events and top 5 in eleven others.

In 2017, Tall Oaks student Nick Yu earned a perfect score and a 3rd place finish in the Delaware Secondary School Mathematics League Invitational Meet.