The family of Oldhall had been settled in Norfolk for at least a century before Edmund’s career began, and had acquired there the manors in East Dereham, Cley and Dersingham, which all descended to him. As his maternal grandfather, Sir Richard Belhouse, died without male issue, Edmund also inherited an interest in the Belhouse estates at North Tuddenham and Wreningham.
Oldhall’s career in royal service began in 1394 when he was named as a j.p. in Cambridgeshire. Before the end of Richard II’s reign he was appointed receiver of the estates of the duchy of Lancaster in East Anglia, and although it is unclear whether he owed his position to John of Gaunt, to the King (following the confiscation of the Lancastrian inheritance), or to Henry of Bolingbroke, there is no doubt that he acted as Henry’s receiver after his return to England in July 1399 and before his accession to the throne. Indeed, before he became King, Henry also appointed Oldhall as receiver of the estates left by the recently deceased duchess of Norfolk, authorizing him in the course of the nine weeks he occupied this post to pay £200 to his supporters, Sir Walter Hungerford and Sir Thomas Beauchamp. Although there were some difficulties over Oldhall’s accounts for revenues collected on the duchess’s property, giving rise to an order in March 1400 for his appearance before the King’s Council on pain of a fine of £400, this did not affect his position in the duchy of Lancaster administration, for he retained his receivership there until his death.
Oldhall was one of the most frequently employed members of the Norfolk gentry in the government of the region, for besides his permanent duchy post he also held office for two terms as sheriff and three as escheator, and served on numerous royal commissions including that of the peace. Some of his duties were far from easy: in 1402, towards the end of his first shrievalty, he was sent letters by the royal council instructing him to obtain benevolences—always an unpopular task; and in August 1414, during his second year as sheriff, having been ordered to supervise the conduct of mayoral elections at Bishop’s Lynn, he found himself ignominiously trapped in the town by Bartholomew Petipas and his armed supporters, who went so far as to break down the bridges and put guards on the gates in order to secure their candidate’s appointment. As sheriff, Oldhall was responsible for holding the parliamentary elections in Norfolk and Suffolk to the assembly of 1414 (Nov.). The office was often a drain on the incumbent’s own resources, and in February following, ‘in consideration of his great losses and costs’, Oldhall was pardoned £100 due on his account at the Exchequer. Rewards for his efforts were otherwise few and far between, although he did secure, in 1412, a share in the wardship and marriage of a duchy tenant; in March 1413 he was one of a syndicate headed by Sir Thomas Erpingham KG which was permitted to purchase from the Crown a number of escheated properties in East Anglia; and, most important, from 20 Nov. 1415 he shared with the bishops of Winchester and Durham guardianship of the temporalities of the see of Norwich during the vacancy caused by Bishop Courtenay’s death.
In the course of his career Oldhall established a number of useful connexions, and no doubt his growing expertise in the sphere of estate management proved useful to those of his acquaintance, among whom were Erpingham, John Spencer and John Wynter, all prominent figures in the households of the King and the prince of Wales. Thus, he assisted Erpingham to make two purchases (of the manor of Cantley in 1401 and of ‘Berney’s Inn’ in Norwich eight years later); in 1408 he was party to transactions regarding manors in Banham which Spencer had acquired, and in later years he acted as his trustee; and he helped Wynter not only when he bought a manor in Saxthorpe in 1409, but also when he came to make settlements of his other estates.
Despite his prominent position in the administration of East Anglia, and his acquaintance among the more influential gentry of the region, Oldhall was himself reluctant to change his social rank by taking up knighthood, and in 1411 he paid a fine to obtain exoneration from so doing. At least five times a knight of the shire, he further showed his interest in parliamentary affairs by attending at the Norfolk elections of 1407 and 1410.