Robert was appointed governor of Porchester Castle in 50 Henry III (1265–6). He accompanied Edward I on Lord Edward's crusade to the Holy Land in 1270. He was made governor of Nottingham Castle in 1275. In 9 Edward I (1280–1) he was appointed justice of South Wales and governor of Cardigan and Carmarthen Castles. Tiptoft was responsible for the compulsory introduction of "English customs" in South Wales which then prompted the revolt of Rhys ap Maredudd in 1287–8.