When Kagekatsu began to show a confrontational attitude towards Ieyasu TOKUGAWA with the chief retainer Kanetsugu NAOE, Nobuyoshi advised Kagekatsu to avoid a conflict with Ieyasu, and also visited Osaka to inform Ieyasu 'The Uesugi clan is not hostile to you,' making efforts to integrate them.
景勝が家老の直江兼続と図って徳川家康に敵対する姿勢を見せ始めると、信吉は景勝に思いとどまるように諫言すると同時に、大坂に上坂して家康に「上杉氏に敵対の意思は無い」と懸命に両家の融和に努めた。