In December 2019, the United States Air Force (USAF) received one of two newest additions to the Gulfstream fleet with the delivery of C-37B, serial 18-1942 (c/n 5586), to Joint Base Andrews (MD). C-37B 18-1947 (c/n 5592) joint in 2020.

On 3 November 2021, the 99th Airlift Squadron at Joint Base Andrews (MD) received a new C-37B Gulfstream G550 (20-1941, c/n: 5613). The US Air Force top military leader Chief of Staff Gen. CQ Brown, Jr. flew the first of two new C-37B aircraft from Maxwell AFB (AL) to Andrews. The new C-37B tail number is 1941, in honor of the year the Tuskegee Airmen were founded. The Tuskegee Airmen were a group of primarily African American military pilots (fighter and bomber) and airmen who fought in World War II. At the end of January 2020, the USAF awarded a USD 127,4 million contract to Gulfstream Aerospace for the delivery of two C-37B aircraft. Later on, Gulfstream then brought them up to the C-37B baseline with communications upgrades through L3 Harris, for a total of USD 159 million. 20-1941 was the sixth C-37B to be added to the 99th AS and the third 89th AW frame to receive its tail number from a key point in US military aviation history.

The 7th and last C-37B (besides 5 C-37A's) for 99th Airlift squadron was delivered to Andrews AFB (MD) on 15 February 2022 as 20-1949 (c/n: 5614). Also this tailnumber (1949) reflects a key point in US military aviation history. 1949 is dedicated to the year of the Berlin Airlift, one of the biggest airlift operations in history, mainly to support the Western part of Berlin with food, medicines and other supplies (credit: Scramble Magazine).