There is no record of when or where Henryson was born or educated. The earliest found unconfirmed reference to him occurs in September 1462 when a man of his name with license to teach is on record as having taken a post in the recently founded University of Glasgow. If this was the poet, as is usually assumed, then the citation indicates that he had completed studies in both arts and canon law. With no record of him as a student in Scotland, it is normally thought that he graduated in a university furth of the land, possibly in Leuven, Paris or Bologna. This has not been established.
Almost all early references to Henryson firmly associate his name with Dunfermline. He probably had some attachment to the city's Benedictine abbey, the burial place for many of the kingdom's monarchs and an important centre for pilgrimage close to a major ferry-crossing
en-route to St Andrews. Direct unconfirmed evidence for this connection occurs in 1478 when his name appears as a witness on abbey charters. If this was the poet, then it would establish that one of his functions was as notary for the abbey, an institution which possessed and managed a vast portfolio of territory across Scotland.
The almost universal references to Henryson as schoolmaster are usually taken to mean that he taught in and had some duty to run the grammar school for Dunfermline's abbatial burgh. A partial picture of what this meant in practice may be derived from a
confirmatio of 1468 which granted provision to build a "suitable" house for the habitation of a "priest" (as master of grammar) and "scholars" in Dunfermline, including "poor scholars being taught free of charge".
Dunfermline, as a royal burgh with capital status, was routinely visited by the court with residences directly linked to the abbey complex. There is no record of Henryson as a court poet, but the close proximity makes acquaintance with the royal household likely. He was active during the reigns of James III and James IV, both of whom had strong interests in literature.
According to the poet William Dunbar, Henryson died in Dunfermline. An apocryphal story by the English poet Francis Kynaston in the early 17th century refers to the flux as the cause of death, but this has not been established. The year of death also is unknown, although 1498 or 1499, a time of plague in the burgh, have been tentatively suggested. However, Dunbar gives the terminus ad quem in a couplet (usually considered to have been composed c.1505) which simply states that Death
in Dunfermelyne
- ...hes done roune (has whispered in private)
- with Maister Robert Henrysoun.
(William Dunbar,
Lament for the Makaris, lines 81-2)
Almost nothing else is known of Henryson outside of his surviving writing. It is not known if he originated from Dunfermline and a suggestion that he may have been linked to the Fife branch of the Clan Henderson is not possible to verify, although his name is certainly of that ilk.