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[BorkBorkGoesTheCode]

Do I have to send my characters into a hostile area without a disguise?

[Taberone]

Disguise can be trained and levelled up even with 0 points in it, but I'm not sure if the same applies to Sneak. IIRC, Sneak only raises on successful stealth attempts, while Disguise can raise even if you fail a roll.

[BorkBorkGoesTheCode]

What initiates a stealth roll?

EDIT: I mean: What tells the game to roll virtual dice.

[SlatersQuest]

Stealth can be leveled up just like Disguise, but Stealth is harder because Disguise takes precedence over it.

My solution would be to train in a location with an inappropriate disguise but which is good for stealth. Cheaply, this means a black turtleneck while sneaking around in the AM Radio and Cable News stations.

[BorkBorkGoesTheCode]

Thank you.

[Rakeela]

The Ninja Outfit is the ideal stealth trainer outfit.  It offers a bonus to stealth and it isn't the correct disguise anywhere, ensuring that you'll be making stealth rather than disguise checks.