In 1590, Ienori was killed in the offensive and defensive battle at Hachioji-jo Castle during the conquest and siege of Odawara, but after the war, Nobuyoshi and his older brother Terumori were employed by Ieyasu TOKUGAWA, and Nobuyoshi served at the post of a page (1,500 koku [of rice; 1 koku is approx. 180.39 liters]).
1590年、小田原征伐における八王子城攻防戦で家範は討死するが、戦後、兄照守とともに徳川家康に召し抱えられ、信吉は小姓役（1500石）として仕えた。