As others have said, I would recommend your DM consider using the passive stealth check for the PC. This allows the DM to get an idea as to how stealthy your character is normally. If something would change that would cause the characters stealth to potentially change then a roll is most likely needed. What could change that would affect a repeatable stealth roll? I would suggest the following: rain, dense & dry brush, very soft ground or deep mud, dense loose gravel, fog, etc. This is a list of terrain or environmental conditions one would find outside.
Stealth inside is a different matter in my mind. Depending on the materials in the structure the sound from walking may echo through a hallway or may be stopped by sound absorbing materials (i.e. curtains). In addition, the interior of structures have a lot of variation in visibility. The lighting may be bright, dim, or dark. The room may have columns and walls lined with mirrors or polished stone or the walls may be wood or a similar material that does a poor job of reflecting light. The variation from room to room may be enough for a new roll needed in each room. However, in my opinion, if a character has spent enough time in a particular room such that the stealth check becomes repeatable then I would use the passive stealth score.
Some additional things your DM mind find useful regarding the passive stealth score. If the character has advantage on the roll or disadvantage on the roll, then it is a modifier of +5 or -5 respectively. I believe the DM may also choose a number modifier other than that. For example, a passive stealth across dense gravel may be the passive score -2. A passive stealth through dense fog near a wharf may be the passive score +3.
In the end though, it's up to your DM to decide if a roll is necessary. I tend to like less rolls and use passive scores. Other on this thread tend to like more rolls.
Stealth inside is a different matter in my mind. Depending on the materials in the structure the sound from walking may echo through a hallway or may be stopped by sound absorbing materials (i.e. curtains). In addition, the interior of structures have a lot of variation in visibility. The lighting may be bright, dim, or dark. The room may have columns and walls lined with mirrors or polished stone or the walls may be wood or a similar material that does a poor job of reflecting light. The variation from room to room may be enough for a new roll needed in each room. However, in my opinion, if a character has spent enough time in a particular room such that the stealth check becomes repeatable then I would use the passive stealth score.
Some additional things your DM mind find useful regarding the passive stealth score. If the character has advantage on the roll or disadvantage on the roll, then it is a modifier of +5 or -5 respectively. I believe the DM may also choose a number modifier other than that. For example, a passive stealth across dense gravel may be the passive score -2. A passive stealth through dense fog near a wharf may be the passive score +3.
In the end though, it's up to your DM to decide if a roll is necessary. I tend to like less rolls and use passive scores. Other on this thread tend to like more rolls.
