We'd come to what I thought was a good conclusion on this in the commonly misunderstood rules thread, but then I read the Boots of Elvenkind and that opened up the question for me again. It'll take me a bit to explain how, so please bear with me.

First, an example or few.

  1. Alice is invisible. Bob enters the brightly lit room where Alice is. Alice has taken the Hide action, knowing he's coming, but, being invisible, hasn't hidden behind anything. Being invisible, she can absolutely hide in plain sight. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?
  2. Alice is invisible. Bob enters the dimly lit room where Alice is. Alice has taken the Hide action, knowing he's coming, but, being invisible, hasn't hidden behind anything. Being invisible, she can absolutely hide in plain sight. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?
  3. Alice is invisible. Bob (who lacks darkvision) enters the dark room where Alice is. Alice has taken the Hide action, knowing he's coming, but, being invisible, hasn't hidden behind anything. Being invisible, she can absolutely hide in plain sight. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?
  4. Alice is perfectly visible. Having heard Bob coming, Alice hides behind a tapestry in the brightly lit room. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?
  5. Alice is perfectly visible. Having heard Bob coming, Alice hides behind a tapestry in the dimly lit room. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?
  6. Alice is perfectly visible. Having heard Bob coming, Alice hides behind a tapestry in the dark room. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?
  7. Alice is invisible and wearing Boots of Elvenkind. Bob enters the brightly lit room where Alice is. Alice has taken the Hide action, knowing he's coming, but, being invisible, hasn't hidden behind anything. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?
  8. Alice is invisible and wearing Boots of Elvenkind. Bob enters the dimly lit room where Alice is. Alice has taken the Hide action, knowing he's coming, but, being invisible, hasn't hidden behind anything. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?
  9. Alice is invisible and wearing Boots of Elvenkind. Bob enters the dark room where Alice is. Alice has taken the Hide action, knowing he's coming, but, being invisible, hasn't hidden behind anything. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?
  10. Alice is perfectly visible and wearing Boots of Elvenkind. Having heard Bob coming, Alice hides behind a tapestry in the brightly lit room. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?
  11. Alice is perfectly visible and wearing Boots of Elvenkind. Having heard Bob coming, Alice hides behind a tapestry in the dimly lit room. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?
  12. Alice is perfectly visible and wearing Boots of Elvenkind. Having heard Bob coming, Alice hides behind a tapestry in the dark room. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?
  13. Alice is invisible and in a zone of magical silence. Bob enters the brightly lit room where Alice is. Alice has taken the Hide action, knowing he's coming, but, being invisible, hasn't hidden behind anything. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?
  14. Alice is invisible and in a zone of magical silence. Bob enters the dimly lit room where Alice is. Alice has taken the Hide action, knowing he's coming, but, being invisible, hasn't hidden behind anything. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?
  15. Alice is invisible and in a zone of magical silence. Bob enters the dark room where Alice is. Alice has taken the Hide action, knowing he's coming, but, being invisible, hasn't hidden behind anything. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?
  16. Alice is perfectly visible and in a zone of magical silence. Having heard Bob coming, Alice hides behind a tapestry in the brightly lit room. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?
  17. Alice is perfectly visible and in a zone of magical silence. Having heard Bob coming, Alice hides behind a tapestry in the dimly lit room. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?
  18. Alice is perfectly visible and in a zone of magical silence. Having heard Bob coming, Alice hides behind a tapestry in the dark room. Does Bob have Disadvantage on his Wisdom(Perception) check (passive or otherwise) to figure out where Alice is / that Alice is present?


It is noteworthy that while we initially discussed this in the other thread as Boots of Elvenkind making you move silently, they technically only give you Advantage on stealth rolls that rely on moving quietly. Would they apply to all cases, here, where the boots are present? Or only to those where Alice is invisible or in the dark?

Of particular concern, here, is whether Bob gets disadvantage EVER based on the dim lighting, and, if he does, if it goes away if Alice is invisible. The second case would mean that it's possible to make it harder to hide by turning invisible, which seems...counter-intuitive.