However, Wolsey proved himself on a errand to Scotland. Soon after, he proved himself again as a messenger from Henry to the Holy Roman Emperor (Ferguson 72). In 1509, Wolsey was appointed Bishop of Lincoln, and upon the death of Henry VII, was given the position of Royal Almoner in the household of Henry VII's son, Henry VIII (Williams 12). 1510 brought Wolsey even more favor from the young king who, preferring lovemaking and hunting to the political arena, presented Wolsey with the office of Registrar of the Order of the Garter and was permitted to supplicate for the degrees of B.D. and D.D. (Ferguson 91). In 1511, Wolsey proved his growing power when he convinced Henry VIII, who was already openly anti-French, to side with Henry's father-in-law, King Ferdinand II of Spain, Pope Julius II, Holy Roman Emperor Maximilian I, the Swiss, and the Italian city-state of Venice in the Holy League against France. Wolsey aided in the creation and signing of the Westminster Bill between Ferdinand and Henry, promising help to each other against the French (Weir, Henry 140). In 1513, Henry and his fellow members of the Holy League became poised for war with France. Pope Julius bestowed the kingdom of France upon Henry, now all he had to do was win it. He sent an army under the Marquess of Dorset to France that June, but the campaign "ended in inglorious failure" (Weir 151). Wolsey and Katherine however, were able to convince him to mount a second army against France, this time lead by Henry himself (Weir 157). .
When it came to preparing for war, Weir tells us that Wolsey proved his true worth, undergoing a multitude of tasks with good humor and efficiency. Foreign observers noted with astonishment the sheer volume of work that Wolsey coped with, with what was sufficient to keep busy "all the magistrates, offices and courts of Venice" (Weir 157). .
Wolsey had already shown himself worthy in many other ways.