at some point in the first quarter of the thirteenth century, alan was granted a vast swathe of territory in ulster from john, king of england. the transaction itself almost certainly took place in the aftermath of the john's expedition to ireland in 1210. the exact date of the transaction, however, cannot be ascertained due to a gap in english charter records between the months of april 1209 and may 1212. the brunt of john's nine-week irish campaign appears to have been directed at wayward anglo-norman magnates—the troublesome lacy family in particular. with his subsequent destruction of hugh de lacy, earl of ulster, and the confiscation of the latter's irish earldom, john was evidently in a position to reward his own supporters with the lacys' former possessions. a date of 1210 for alan's grant, as well as the possibility of his participation in the english expedition of the same year, may be evidenced by the record of a certain "alan, son of roland" in the king's service that year.