When the king and queen visited their son Sigismund III Wasa in Reval in 1589, he and Axel Bielke was appointed to serve as regent during their absence. He was described as clever and skillful and worked to increase the power of nobility against the crown. He sided with Sigimund III against Duke Charles. His son Svante fled to Denmark after the War against Sigismund to avoid execution. Hogenskild was tried during the Linköping Bloodbath in 1600, but was imprisoned rather than executed. In 1605, however, he was found to have been involved in a correspondence judged as treasonable alongside his daughter Ebba Bielke. He was executed for treason in Stockholm.