In its first decade, the Jolenites were mainly guards and guides, taking food, shelter, or coin in exchange for escorting travelers through dangerous country. Their first major triumph came when they led several stranded caravans through a pass after a local lord's soldiers abandoned the road. The rescued merchants paid generously, and word spread that the Jolenites were dangerous but dependable. The gang's watershed moment came during the Winter of Split Axles. A new ruler declared the Jolenite tolls illegal and sent soldiers to seize the wagons. The gang's then-leader negotiated safe passage for the soldiers' families, then used the resulting confusion to evacuate the wagons and the families together. The soldiers were disgraced, the ruler lost leverage, and the Jolenites became known as people who could turn a threat into a bargain. They also began keeping written records of every debt and promise, a practice that made their extortion more systematic. Over the next two decades, they expanded from escort work into smuggling, protection, and coercive toll collection. A famine made them popular in some villages after they delivered grain past blockades, but they charged those same villages steep fees for later protection. A disastrous feud with the Ash Hounds cost them wagons, members, and a winter's supply of food. The gang survived by relying on local informants and making its collectors more disciplined. Today the Jolenites are a medium-sized traveling organization with enough reach to influence several routes, but not enough power to enforce every promise. Their old tradition of protecting travelers now coexists with a predatory toll system. Members argue over which side is the real Jolenite inheritance.

The Jolenites have no fixed headquarters. Their moving center is a ring of wagons arranged around a cooking fire, with the lead wagon facing the next day's road. At least one wagon is always awake, and the camp is laid out to become a defensive barricade in minutes. Their meeting place is wherever the wagons stop, though senior members keep a covered chest of records and seals in the central cart.