Roualeyn was educated at Shrewsbury School and Magdalene College, Cambridge, where he took a first in classics. He became an honorary Fellow at Magdalene in 1977. Cumming-Bruce was an active communist whilst at Cambridge, once arguing during a debate at the Cambridge Union that "hope lay in the adoption of the Soviet system – a system which combined the spirit of democracy with swift and certain action."T. E. B. Howarth, Cambridge Between Two Wars (London: Collins, 1978), p. 224.
