In February 1921, he led the disastrous Upton Train Ambush on 15 February 1921, an attack on train carrying British troops. In the action, the attacking IRA party was heavily outnumbered and the fire fight resulted in three IRA men and six civilians being killed. Hurley was also badly wounded in the face and ankle. Tom Barry wrote of the aftermath of the ambush 'he [Hurley] mourned deeply for his dead comrades and for the dead civilians, whom he did not know'.
Hurley was killed in action by British troops just before the Crossbarry Ambush on 19 March 1921. Hurley was staying in a house with a pro-republican family, where he was recuperating from serious wounds he had received at Upton a month earlier. When he realised that he was surrounded by the British forces he fled the house, as Tom Barry comments in his book, to reduce the danger to those in the house, and was shot dead by pursuing troops. Barry remarks that Hurley, 'died in the manner in which we expected.'
The British Army placed his body at the workhouse in Bandon but members of Cumann na mBan surreptitiously took away his body and he was given a secret republican funeral in Clogagh. A local ballad exists that commemorates him. In addition, the Gaelic Athletic Association grounds in Bandon was named after him in 1971.