D&D 5E 5e Skill Challenge help

Nebulous

Legend
I know this has cropped up before and I read a few threads, but I wanted to get some new insights. I haven't used Skill Challenges since 4e, and not often even then, so it's been a super long time. I recall borrowing ideas from the Obsidian Skill Challenge, but I think that was more complex than the default rules. SC can seem VERY gamey, so it's more of an art to it than a skill to make them fun and organic. I also have a 5e pdf from DMGuild but it doesn't have good concrete examples, it just says look up old 4e stuff. I admit that skill challenges was never something I was great at although I did recognize the potential in them.

Here's the setup: the PCs will be traveling overland from Cragmaw Castle to find Wave Echo Cave, led by Reidoth the druid (NPC). It's roughly 8 to 10 hexes away, 40-50 miles. I normally roll random encounters, but I want to eschew that idea and instead do THREE challenges:
Easy, Medium and Hard (DCs 10, 15 and 20 respectively). I thought I would do a social encounter, a hazard encounter and a combat encounter (Easy, Medium and Hard respectively).

Easy (social): The PCs are near the Triboar Trail and camping for the night when a group of travelers join them. The travelers are actually bandits and will lull the PCs into trusting them so they can be robbed, pickpocketed, etc. (4 successes before 3 failures). How are some ways that this can play out in real time as the players use skill rolls? I am VERY rusty at challenges and forgot how to make these things flow well.

Medium (hazard): Flashflood in the foothills. A torrential rainstorm fills a canyon and the PCs have to navigate to safety or lose HD or gear or gain Exhaustion or a combination. (6 successes before 3 failures). I guess this will mostly end up being physical challenges for the players, but I could use some examples of how others have done this.

Hard (Combat): In the mountains, not far from the entrance to Wave Echo, they stumble across Mondo the Hill Giant. He's big, he's stupid, he's an naughty word, and CAN kill the 4th level party pretty easy. (8 successes before 3 failures). This would only devolve to combat if they fail the challenge, OR I can knock them down HD automatically and say they escaped, or it takes days to circumvent Mondo and they gain Exhaustion by having to climb steep alternate routes.

Any suggestions are welcome.
 

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I don't think the math necessarily works the same for D&D 4e skill challenges in the context of D&D 5e. The rules for skill challenges had a lot of particular requirements. See the D&D 4e Rules Compendium for the most up-to-date skill challenge structure.

While I don't think you can import them directly to D&D 5e, for any given exploration or social interaction challenge I think it's fine to come up with a number of complications, obstacles, or objections to overcome and set some kind of requirement for success in the overall challenge. Present each complication, obstacle, or objection and ask an individual PC how he or she deals with it. If what the player proposes has an uncertain outcome and a meaningful consequence for failure, then ask for an ability check. Once resolved, present the next complication, obstacle, or objection and call on a different PC for a response. And so on until the challenge is completed and you can tally up successes against failures to narrate a result of the adventurers' actions.

In this setup, you only need to come up with a list of complications, obstacles, or outcome objections that fall under the overall theme, so the prep is easy. Which ability checks and DCs there are can only be determined after the player describes what he or she wants to do about them.
 
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In this setup, you only need to come up with a list of complications, obstacles, or outcome that fall under the overall theme, so the prep is easy. Which ability checks and DCs there are can only be determined after the player describes what he or she wants to do about them.

Thank you. And that's what I'm trying to do, have a list of outcomes under each theme. What skills and how to use them will fall to the players. And this might not work well, but I wanted to try it and see how it pans out.
 

Sorry, "outcome" was a typo on my part. That should be "objection." Outcomes can't be determined until the players say what they want to do and the ability check, if any, is resolved.
 

Here's the setup: the PCs will be traveling overland from Cragmaw Castle to find Wave Echo Cave, led by Reidoth the druid (NPC). It's roughly 8 to 10 hexes away, 40-50 miles. I normally roll random encounters, but I want to eschew that idea and instead do THREE challenges:
My inclination is to do one Skill Challenge for the journey, with complications - like a 'random' encounter or loss of time and/or HD to a hazard - for each failure before the requisite successes complete the journey. There's no reason to even stop at 3 failures, either, the journey just keeps getting worse and worse... ;)
 

My inclination is to do one Skill Challenge for the journey, with complications - like a 'random' encounter or loss of time and/or HD to a hazard - for each failure before the requisite successes complete the journey. There's no reason to even stop at 3 failures, either, the journey just keeps getting worse and worse... ;)

That's another way to do it. But does that mean I need a list of all...um potential failures along the way? It should only take them 3 days max to reach their destination, which would normally be six random encounter rolls (assuming a morning and night encounter, which I usually roll 17+).

Let me phrase that another way: How do I set up a single skill challenge covering three days?
 

That's another way to do it. But does that mean I need a list of all...um potential failures along the way? It should only take them 3 days max to reach their destination, which would normally be six random encounter rolls (assuming a morning and night encounter, which I usually roll 17+).
You can base the type of consequence on the check failed. For instance, failed Perception or a failed group stealth check could result in a encounter. Failed survival or nature could result in problems with a hazard.

Let me phrase that another way: How do I set up a single skill challenge covering three days?
In addition to having consequences of failures ready (and the three challenges you have, the bandit encounter, the flash floods, and the Giant could work as failure consequences, for instance, as could the denizens of your usual random encounter table), you could decide the journey is hard enough that you only get the benefits of a short rest overnight, and can't get a long rest until the journey is complete (or even until after the journey back, for that matter).
 

You can base the type of consequence on the check failed. For instance, failed Perception or a failed group stealth check could result in a encounter. Failed survival or nature could result in problems with a hazard.

In addition to having consequences of failures ready (and the three challenges you have, the bandit encounter, the flash floods, and the Giant could work as failure consequences, for instance, as could the denizens of your usual random encounter table), you could decide the journey is hard enough that you only get the benefits of a short rest overnight, and can't get a long rest until the journey is complete (or even until after the journey back, for that matter).

Oh that's a good idea, hazardous weather or conditions prevents a long rest overnight and results in only a short rest. I've been trying to come up with ways (HD and exhaustion) to target them, and taking away easy long rests is another route. The party would just delay another day to rest up, but that could result in more random encounters, and thus more resources lost.
 

Oh that's a good idea, hazardous weather or conditions prevents a long rest overnight and results in only a short rest. I've been trying to come up with ways (HD and exhaustion) to target them, and taking away easy long rests is another route. The party would just delay another day to rest up, but that could result in more random encounters, and thus more resources lost.
Yeah, in 4e I'd routinely do that just as the format for journeys: there's a skill challenge - encounters, surges lost to hazards, etc, are consequences of failed checks along the way - only short rests during the journey, long rest waits until you reach the destination (or, as I suspect'd be the case, here, after the return journey, since the destination, itself, sound hazardous).
 

Yeah, in 4e I'd routinely do that just as the format for journeys: there's a skill challenge - encounters, surges lost to hazards, etc, are consequences of failed checks along the way - only short rests during the journey, long rest waits until you reach the destination (or, as I suspect'd be the case, here, after the return journey, since the destination, itself, sound hazardous).

Well Wave Echo Cave is a pretty huge area, they will have to long rest at some point. Probably not in the cave though.
 

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