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Message: <blockquote data-quote="iserith" data-source="post: 6823802" data-attributes="member: 97077">You can try to be alert and ready for hidden dangers in general and not specifically searching out a hidden danger known to you. In the event the outcome is uncertain, the former calls for a passive Perception check; the latter calls for a Wisdom (Perception) check. The key thing is you can't be alert to hidden dangers in general and also be doing anything that is at least as distracting as navigating, drawing a map, foraging, tracking, etc. Unless, of course, you're a ranger in favored terrain.With regard to the initial post, the issue at hand is how the DM is resolving the actions described by the player. If the DM is always going to use the dice to determine the outcome of stealthy activity, then I would suggest investing in resources that will increase the Stealth bonus as high as possible. Multiclassing as a rogue and taking Expertise is a potential option, as is seeking out magic items that grant advantage to Stealth checks such as a cloak of elvenkind. If the DM sometimes rules outright success or failure and sometimes asks for checks based on how the player describes what he or she wants to do, then I would suggest paying attention to and engaging with the environment as described to eke out an advantage by seeking outright success.</blockquote>