In a famous letter to his missionaries in England, Pope Gregory the Great suggested that the newly converted Anglo-Saxons should be encouraged to build small huts, or ‘tabernacula’, in conjunction with Christian festivals. He seems to have associated these structures with the Jewish festival of Sukkot, reflecting a missionary strategy modelled on both the biblical conversion of the Israelites and on Gregory's own proselytizing approach towards the Jews of Rome. Gregory's instructions are discussed in the light of historical writings and archaeological evidence, which suggest that ‘tabernacula’ were indeed constructed in England during the conversion period, possibly adapted from pre-Christian Anglo-Saxon ritual structures.