In the later middle ages in England, military service increasingly became based on service contracts, either for long or short periods. The earliest such short term contracts (that we have found) date from 1270 CE, when Prince Edward (later King Edward I) paid a company of knights to serve with him on the Eighth Crusade for a year's time. There are earlier references to such arrangements as well. Military service contracts began to increase in importance starting from the 1290s, until the 1330s, when an entire field army would have been fielded through the mechanism of contracts (whether for life service in a retinue or for a specific campaign).

The primary benefit of signing such a contract and fighting for the king in France or Scotland was being paid. Aside from the regular daily wage of a man-at-arms or an archer, there were several other benefits. Mounted troops could recieve the restauro equorum, which provided for compensation in the event that a man's horse was killed or lost in battle. Regard was a bonus payment to captains and officers to cover the general costs of raising a company and leading it in the field. Bonuses might also be paid in the aftermath of a major battle, if the king or one of his advisors thought a man or a company had fought particularly well.

Soldiers could also loot conquered towns or victorious battlefields for the copious amounts of booty free for the taking. In the aftermath of battles like Crecy (1346), where the bodies of thousand of French aristocrats littered the field, the pickings could be extremely lucrative. The exact division of spoils varied, but at Crecy, half of a man's spoils would be forfeit to his captain, who would then hand over half of that half to the king. Ransom from prisoners counted as spoils in this circumstance, although English tactics often ensured that there were very few prisoners remaining by the end of a battle. With extremely important prisoners (like a French noble of royal blood, or an important noble from some other kingdom), the king had the right to take custody of these prisoners from the soldiers who had captured them. If this ended up being the case, it was usually expected that the king would pay compensation to the soldier who had been deprived of a ransom. However, that depended on the generosity of the king at that particular moment.

There were several legal benefits available as well for soldiers. Convicted criminals might serve in exchange for a royal pardon. There were two main benefits to this: 1) Convicts often would be required to fight without drawing a wage and 2) criminals generally paid a fee in exchange for their pardon. Men with what Andrew Ayton calls "significant property interests" could get a letter of protection for his lands after he signed up for military service. This meant that his estate and lands were secure from being sued when he was away. Without this protection, landowners wouldn't be able to leave England to fight.

Of course, this is all in ideal terms. Often, wages were not paid, or if they were, were insufficient. Sometimes wages were only paid to men who had achieved some kind of political influence years after their actual service. Henry V was forced to pawn off many of his royal jewels in order to convince nobles to serve and to receive loans from towns. War debts escalated wildly for the English crown over the course of the Hundred Years War, which contributed to the eventual English defeat. Henry VI was so desperate to find additional sources of revenue that he formed a committee of alchemists to try and make gold for the crown.