Sugar Shadows mostly consist of Jamanni Clan's former retainers who did not agree with S'var-Lhajiito's rule. Following the signing of the business contract with Ya'Tirrje, the Gold Cat, in 2E 879, Rak'sad, an advisor to S'var-Lhajiito, expressed his disappointment due to the unprofitable position in the skooma market gained by the Jamanni. Rak'sad then formed the Sugar Shadows alongside his lieutenants Adargo and Khit. Sugar Shadows were responsible for stealing most of the Moon Sugar and Skooma supplies which belonged to both the Jamanni and Ya'Tirrje. Their other activities included sugar smuggling, destruction or capture of plantations and, in some cases, assassinations.
It is speculated that Sugar Shadows are partially involved in Jamanni Clan's crippling and decline in early Third Era. The smuggling faction exists to this day.
Like the Jamanni, Sugar Shadows' favored skills were:
Sugar Shadows did not practice magic much, most often relying on stealth and combat.
- Footpad - the lowest rank within Sugar Shadows. Footpads are most commonly trained in Light Armor and utilize daggers and shortswords in combat.
- Blackcap - those retainers are fairly skilled in Light Armor, Sneak and Marksman. In most cases, Blackcaps prefer striking from the shadows, using bows and, rarely, crossbows. They switch to daggers if engaged in close combat.
- Agent - skilled in both Light and Medium Armor, as well as Short Blade and Security, Agents are formidable opponents in combat and almost invisible when sneaking.
- Thug - a tough foe that tricks opponents by hiding in the shadows during combat, and then reappearing from behind. Thugs are trained in Light and Medium Armor, Sneak and Blunt Weapon.
- Ringleader - skilled in everything but Marksman and Medium Armor, Ringleaders are an uncommon rank. They are given their own piece of land as well as a group of Thugs to control within Sugar Shadows.
- Sugar Finger - a unique rank. Only one Sugar Finger can be active at one time. Sugar Finger operates exclusively under moonlight, and gets missions directly from the boss.
- Lieutenant - Lieutenants are the most trusted members. They are the advisors to the leader, and are skilled in everything but Blunt Weapon. Lieutenants are the ones that grant Ringleaders their respective property and Thug groups.
- Redcap - the highest rank within Sugar Shadows. Trained in every favored skill of the faction, Redcaps are the leaders. A Redcap is chosen among the Lieutenants by all members after a previous leader passes.
A list of most prominent members of Sugar Shadows:
- Rak'sad - a former advisor to S'var-Lhajiito and founder of the faction. Redcap.
- Adargo - a former retainer of Jamanni Clan and Rak'sad's lieutenant.
- Khit - a former retainer of Jamanni Clan and Rak'sad's lieutenant.
- Khamuz - Zahraji's aunt and a high-ranking member of Sugar Shadows. Ringleader.
- Gajaran - a member of Sugar Shadows who was accused of stealing Masser and Secunda in an event known as the Void Nights. Sugar Finger.
- Baadar - a retainer residing at Redfur Trading Post. Thug.
- J'hatt - a retainer residing at Redfur Trading Post. Thug.
As of 4E 202, the Sugar Shadows have no Redcap; Ra'zirr, a Lieutenant and Khamuz' descendant, is in charge of the faction until a worthy Redcap is chosen.