Still in their infancy as an organization, the wilderness scouts who patrol beyond Freehold's borders began as a rangers' guild proposed by Adoward Beastfriend, Samuel Fisher, and Lysander Arkaine; however, due to differences in ideology, the proposal was quickly separated into a disparate "hunters' guild" and what is slowly becoming known as the Greencloaks. The name is taken from the Cormyrian Special Forces, who were especially active during the Goblin Wars of 1370—1371DR; though the original Greencloaks were specially trained for woodland operations, at the basic level they were survivalists and stealth infiltration experts whose skills could reasonably apply in any environment. It was this underlying principle that saw the beginnings of the Freehold Greencloaks.

While initially granted a basic formal guild charter by the First Freehold Council, the small, loose operation is intended to be considered a public entity; however, the membership of the Greencloaks, as a whole, is held personally responsible for the actions of all members. Greencloaks are ultimately answerable to the Freehold government, and are considered public servants while they maintain membership—while they are expected to police their own membership, public complaints can be filed to request an injunction for irresponsible use of authority, and members found to be guilty of any crime within the bounds of Freehold proper are subject to all applicable laws, fines, and punishments, as appropriate. This is important because, outside the boundaries of Freehold proper, Greencloaks are held to a strict code of service in place of Freehold law:

Suffer your homeland to bow before no one. Be ever watchful, ever ready. Let death never be the first answer, but always the last word. If the end must justify the means, then must the end be worth more than a single man, or the burden on his soul.

According to the code, a Greencloak cannot be punished within Freehold for actions committed outside its boundaries that would normally be classified as criminal, so long as those actions involve the direct defense of Freehold's people against a provable threat. This suspension of limitations is to be clearly understood as a license to protect Freehold, not as an excuse or a motivation for "assisting" in expanding its borders, its fortunes, or its power base. A Greencloak who breaks their oath or abuses their power in the field, to the detriment or incrimination of the force or of the people of Freehold, individually or as a whole, is expected to be executed by their fellows or otherwise brought to swift justice. While this may sound harsh, it is also not widely spoken of nor regarded as totally unfair, since the purpose of the organization is to serve as Freehold's first line of defense and early warning/prevention system.

The Greencloaks function under the de facto leadership of Lysander Arkaine, who prefers not to use that name for them, but the term is already gaining popularity following Raxam Kelastro's idly repeated comparisons, against their founder's wishes.