The son of a town education officer, Kesselring joined the army as a cadet in 1904. After serving in World War I and remaining in the army under the Weimar Republic, he transferred to the Luftwaffe (air force) in 1935 and a year later was promoted to lieutenant general and chief of the General Staff of the Luftwaffe. Early in World War II Kesselring commanded air fleets in Poland (September 1939) and France (May–June 1940) and during the Battle of Britain (1940–41). Having already had experience in the bombing of civilian population centres such as Warsaw and Rotterdam, he apparently concurred in Hermann Göring (Göring, Hermann)'s decision to redirect Luftwaffe bombing toward London. This proved to be a fateful decision because the resulting discontinuance of attacks on British airfields gave the Royal Air Force Fighter Command time to recover and eventually defeat the German air offensive against England.

After participating in the attack on the Soviet Union (summer 1941), Kesselring became commander in chief, south (late 1941), to bolster Italy's efforts in North Africa and against Malta. Though unable to take Malta, he commanded Erwin Rommel and the Axis campaign in North Africa. After the Allied invasions of Sicily and Italy in the summer of 1943, Kesselring fought a brilliant defensive action that prevented an Allied victory in that theatre for more than a year. Injured in October 1944, he became commander in chief, west, in March 1945, replacing Field Marshal Gerd von Rundstedt, but proved unable to stop the Anglo-American drive into Germany and surrendered the southern half of the German forces on May 7, 1945. He remained loyal to Hitler to the end.

In 1947 a British military court in Venice tried and convicted Kesselring of war crimes—for ordering the shooting of 335 Italian civilian hostages in the so-called Ardeatine cave massacre of March 1944, an atrocity committed in reprisal for an attack by Italian partisans on German soldiers. Sentenced to death on May 6, 1947, Kesselring later won commutation to life imprisonment. In 1952 he was pardoned and freed, and he became active in veterans' organizations. He wrote Soldat bis zum letzten Tag (1953; “Soldier up to the Last Day”; Eng. trans. The Memoirs of Field Marshal Kesselring).