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Stormcloak Prisoners are one of many Random Encounters that occur along roads. These men or women will spawn with an Imperial vanguard and when activated will present the player with 3 options: leave them alone, free them, or free them and trade weapons/armor with them. Doing either of the latter actions will cause the guards escorting said prisoner to become hostile. If you do not give him/her any equipment, they are likely to die. It appears there are no actual advantages to assisting these NPCs, even if following the Stormcloaks storyline. If the player chooses to escort them once the NPC reaches the gates of Windhelm they will go inside and despawn (they cannot be found inside Windhelm).
If the player kills the Stormcloak Prisoner undetected and then reanimates the corpse with a sufficient conjuration spell, scroll or staff, the small Imperial Legion detail will follow the prisoner wherever he goes. Summarily, for the duration of the reanimate corpse spell, the player will get 3 followers. This can be useful if the player is nearing hostile territory or Forsworn strongholds as the Legionnaires will respond aggressively to hostile members of other factions.
Conversely, if the player lands a sneak attack on the prisoner without killing him / her, and the prisoner becomes hostile towards the player, the Legionnaires will kill the prisoner.
- The Elder Scrolls V: Skyrim (First appearance)