- "Riley, you comin'? I'm growin' a beard waitin' for ya!"
- — Anderson to Riley.
As German forces attempted to breakthrough the Allied lines in the Ardennes Forest with the intent of capturing the strategic port in Antwerp, Anderson as well as the rest of the 506th were rushed to the crossroad town of Bastogne. The 506th arrived on 19 December and was placed on the northeastern flank of Bastogne to halt the German advance from Foy. As 2nd Battalion arrived on the frontline, it dug in, preparing for an attack from the 76th Volksgrenadier Division and 2nd SS Panzer Division. On 26 December, the Germans launched a large scale assault on the American line. Anderson accompanies Riley to their foxhole, and moves down the line as the attack shifts towards the right flank. Repelling several armor attacks, the line is eventually relieved by a formation of Sherman's ending the battle.
On 13 January 1945 around 0200 Hours, Anderson participates in a coordinated attack on the crossroads just south of Foy, rescuing a missing combat patrol and facilitating the attack on Foy itself later the day. At 1100 Hours, Anderson, along with the rest of Fox Company, initiates the attack on Foy, defeating a large German force, destroying a small armored unit, and capturing the town. Two days later on 15 January, Anderson would take part in the attack on Noville, capturing the city and repelling a massive German counter offensive until reinforcements and air support arrives.