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Message: <blockquote data-quote="Quickleaf" data-source="post: 5279810" data-attributes="member: 20323">Awesome <img src="https://cdn.jsdelivr.net/joypixels/assets/8.0/png/unicode/64/1f60e.png" class="smilie smilie--emoji" loading="lazy" width="64" height="64" alt=":cool:" title="Cool    :cool:"  data-smilie="6"data-shortname=":cool:" /> Sounds like a great first skill challenge.I did something similar with a masquerade ball where the PCs had to make contact with an informant without revealing themselves (or the informant) to other spies hidden in the masquerade.So, here are ideas specific to your scenario:* Is the mark already tipped off that the PCs are pursuing them? Do the PCs have an option of silently tailing (at least for a while)?* Nature could be used to navigate around animals in the masquerade, like a painted cow or a flock of pigeons? Or it could be used to identify flow of certain canals or where a fogbank might be? Or even piloting a gondola?* In a Venice-like city Perception has tons of uses, like noticing a subterranean passageway going underneath a canal or a series of passing boats than could be used as stepping stones with the right timing? Or to notice a change of cloaks/masks or unusual reactions of crowd to someone rushing thru?* Diplomacy could be used to quickly haggle with a merchant for something useful to the chase, to show proper decorum through a crowd of dancing revelers, or to convince a guardsman to get help?* Are the PCs already familiar with the mark? Insight could anticipate their next move or possible ways they'll try to shake the PCs?* What is the religious significance of the masks? Religion could help the PCs anticipate what comes next, the symbolism behind certain masks, or ways to get out of being hassled by masked priests?* What is the nature of the enchantment? Does it create an arcane signature which a character with Arcana could sniff out?Here's my advice about skill challenges in general:Think of a skill challenge as a solo monster - what makes a fun solo monster? For example, solos often change when bloodied, so consider having events which occur during the SC either independent of PCs' actions or caused by them.Consider whether you want to announce it as a skill challenge or not. This depends entirely on your group's preference for transparency.Players unused to SCs might be unsure of their options, and might be hesitant to participate. You might provide some examples of what they can do by describing the scene vividly or focusing your description on certain features.Once players get the hang of a SC they'll start jumping in with ideas. I quickly abandoned tracking initiative and let them go in whatever order they want (so long as each turn everyone gets an action).Players have a disincentive to participate with low skills because failure is worse than inaction in a SC. My best advice is to include as many skills as possible when designing the SC; in other words there should be a time and place for nearly every skill to be used during the SC.Avoid arbitrary restrictions like auto-fails or closing off a skill entirely.Include other options You either fail or you succeed in a SC. However, I find that having multiple possible outcomes dependent on degree on failure/success is more interesting since SCs rarely are as "binary" as combat.Good luck with it, and let us know how it turns out!</blockquote>

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