While I have heard rumors that there are DMs who rule otherwise, in almost 20 years of playing D&D I have never seen a DM rule that a failed stealth check meant anything other than one thing: you’re caught. Recently when a friend of mine retired his 5e Rogue character he lamented that D&D was not really fit for characters who wanted to resolve problems outside of combat and his preferred method for handling challenges with that character, mainly using stealth and subterfuge, were handled via binary pass/fail ability checks.
Following that conversation, I decided to develop a system that made non-combat resolution a little more viable by introducing shades of success. In combat, characters gradually reduce the hit points of their enemies earning a victory bit by bit. In this new stealth system, Strongholds & Sentinels, characters earn their victory bit by bit by sneaking from one place to another while slowly building up to a showdown with each failure.
Another merit of a defined stealth system is that it helps DMs and players share expectations of what the game is about. In a campaign where the DM rules that Strongholds & Sentinels will feature, players can be assured that proficiency in stealth related skills will pay off and character concepts that emphasize subterfuge over direct aggression will have a place.
But enough talk, now is the time for deliberate silence…