Transcript from a recent game
Dwarf Priest "Hey, send someone across the field to see if there's any baddies waitin' on us in the winery!"
Elf Wizard "But... the rogue didn't come tonight... his kid had baseball or something..."
Dragonborn Trickery Domain Cleric "I've got this! I cast Pass Without Trace on myself!"
DM "OK, you cast Pass Without Trace. Your party members find it harder to notice you. You have to maintain concentration on this. The field is completely open between the tree line where you guys are and the winery. Also. It is fairly bright out right now. It's about noon and the weather is good. Tell us how you plan to approach the winery."
Dragonborn Trickery Domain Cleric "I'm just gonna run across. I'll use dash and cross the distance quickly before anyone spots me!"
Human Paladin "In your armor? Aren't you wearing chainmail? That'll be noisy!"
DM [looks it up and confirms that stealth checks are at disadvantage while in chainmail. He says nothing, but kinda chuckles to himself imagining the possibilities]
Dragonborn Trickery Domain Cleric "OK. You're right. I won't need it. I take my chainmail off and hand it to the Paladin for safe keeping"
Elf Wizard "This doesn't sound like a good idea..."
Dragonborn Trickery Domain Cleric "OK. Ready. I'm running across"
DM "You dash across the field magically concealed, but not invisible." [DM looks up the cleric's passive perception] "As you approach the building, you see multiple figures inside actively looking outside, and you also note multiple figures outside keeping guard that were not previously visible from where you were at. I need you to roll a Dexterity (Stealth) Check. This is not an easy situation to hide, but you get to add +10 for Pass Without Trace."
DM is thinking of how to mediate this.. maybe set a DC of 15? that's very generous because he's thinking that really it should be 20 but if they fail there will be a bloodbath.. or maybe do opposing Stealth vs Perception checks?
Dragonborn Trickery Domain Cleric [rolls...] "I rolled a 1...."
Elf Wizard "..."
DM "I need you to roll for initiative while 10 blights move in on the cleric's position with multiple more inside. The party will need a round to run up to your position. And.. remember that you don't have any armor on."
Hilarity ensues...