Form 1403 he was in the service of Henry of Monmouth, Prince of Wales, guarding the Welsh Border.

With his company of esquires and archers, Talbot defeated a superior Welsh force at Grosmont, Monmouthshire, in 1404.

After a trip to Ireland under Thomas of Lancaster in 1408 he joined forces with his brother John to recapture Harlech Castle from Owain Glyndŵr later in the year.

He succeeded to his mother's title in 1413, becoming 8th Baron Strange of Blakemere and was appointed Chief Justice of Chester in 1413.

He was appointed Captain of Caen Castle in 1418 and in the same year involved in the successful sieges of Domfront and Caudebec.