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N'raac Here is an example from a social Skill Challenge in my home game that went horribly awry in the same way that the one outlined above went extraordinarily well. It makes have use of the technique of "Fail Forward" so I suspect it will be very averse to your tastes. But I just wanted to show it to you as an example that things can go terribly wrong just as they can go terribly well. It was remarkable/memorable to me for two reasons:
1 - It was only a complexity 1 Skill Challenge that extraordinarily went south and went south hard due to a series of wonky die rolls.
2 - The impact on the resolution of the final tier of play, and afterward, was fairly significant.
The tier of play being resolved was a riff off the classic trope (Gap of Rohan, Thermopylae Pass, The Wall in ASoF&I) of hopelessly outnumbered, but utterly committed, defenders heroically defending the lone breach to civilization from an oncoming horde. In this case it was a mixed horde of human barbarians and monstrous creatures versus several settlements on the edge of civilization where various Ranger Lodges have been watching and defending this breach throughout history. However, the old allegiances had died and it was a fractured fraternity. The PCs task was to "unite the clans (lodges)" by convincing each High Huntsman (the leader of the lodge) of the impending threat. This particular lodge had a very proud, very severe half-orc as High Huntsman. Of note, in my game the elf/orc feud is not one of socialization, its born of the Gruumsh/Correlon creator influence; effectively magical (genetic) predisposition. "Its in the blood." Half-orcs are not free of this. Two of my 3 PCs are elven (one is technically eladrin...but elf nonetheless).
B (Bladesinger), R (Rogue), D (Druid)
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They arrived in his village with children playing, practicing archery, tanners tanning, warriors practicing morning drills with the great half-orc huntsmen chopping great blocks of wood on a redwood stump.
The initial scene Bang involved the aformentioned, archery-practicing-children enamored of an elf (Eladrin Bladesinger) and his beautifully carved bow. They wanted to see the bow and they wanted him to show them the legendary elven technique and accuracy. He indulges them...in eyeshot and earshot of the half-orc High Huntsman and the proud warriors of his clan...
0:1 - (B) Dexterity check + Bow proficiency bonus + magic item bonus (would have added + to hit from Expertise etc if he had it as well) versus Moderate DC. The Bladesinger lets them see the bow, pull back the string, etc. At their behest, he lets loose an arrow at their target and hits it square in the middle, cheers abound.
Mechanically this was a failure by 1. Complication: The High Huntsman is not amused. He is visibly offended, big time. He grunts disdain and snorts something under his bread, slamming his axe home and splitting a log in one fell blow.
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SA - (D) Insight support action versus Easy DC. The elven Druid takes measure of the High Huntsman's "not amused" response to the foreigner elf proposing to "instruct" the children of his clan on archery...of which their lodge is legendary for. She gives gives a brief look of acknowledging consternation to the Rogue for his follow-up effort at damage mitigation.
Mechanically a success so a + 2 to the Rogue's next check below.
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0:2 (uh oh) - (R) Diplomacy versus Medium DC. The Rogue attempts damage control, making note of and praising the lodge's legendary reputation as archers...and make, hopefully, a mood-lightening joke at the naive elf's expense.
Mechanically this check was impossible to miss...yeah, except he rolled a 1. There was an amusing facepalm moment here. Complication: The High Huntsman acknowledges the Rogue's words, says "yes, he is clearly a fool...state your purpose." However, his top warrior (also offended and unwilling to let it go at that) walks over, focuses his ire squarely on the elf and begins to recount a folk tale about the wolf going into the bear's den and "rearranging the place." He asks the elf he knows it.
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1:2 - (B) He pondered going with Intimidation (he would have used the Spook Cantrip; sub Arcana for Intimidate) here, but went History check versus Medium DC (as the opportunity presented itself, making sense in the narrative and allowing him to keep Spook in his back pocket should it be needed later). He dispassionately finishes the story about the bear waking up and eating the wolf. The two warriors stand not far from each other, looking grimly at each other.
Mechanically an easy success. Result: The High Huntsman, amused, lightens for a moment and asks them "are you here to scare me and my clan into being the levee overcome by the great flood?"
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SA - (D) Intimidate support action versus Easy DC. The Druid attempts to relate that the great food is all-consuming. All of the land is washed away, the animals, the trees, everything...not just the breaking levee. Hopefully setting up the Rogue for a follow-on.
Mechanically. Yeah, inexplicably she fails. - 2 to Rogue's upcoming check. Complication: Exhausted and the interruption to his morning work, he lashes out at her, irrationally blaming her for distracting him when his favorite wood-cutting axe becomes lodged in an unforgiving knot in his next blow. He lets go of the stuck axe, backs off and wipes his sweating brow, catching his breath.
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1:3 - (R) Athletics versus Hard DC. Going to do the mechanic part first here. An interesting thing happened here. Before the Skill Challenge, the Rogue invoked the Martial Practice Uncanny Strength (10 minute duration, take 10 on Athletics checks for a Healing Surge). If the Druid passed her Intimidate support action, that would have given the Rogue an automatic success versus a Hard DC with Athletics. Now, with a failure, he needed a 13 or better. He still could have auto-passed on a Moderate DC but he wanted this to be narratively impactful and they needed to rally. He bartered for the Hard DC for 2 successes in the challenge. Rolled an 11. Yeah. Aggressively and assertively, the Rogue tore the deeply buried axehead free of the knot in the half-split log. Before he sent it down, he made some sort of symbolic statement (invoking the spirit of the flood metaphor) like "a swing from each of your lodges and the horde will be rent asunder" and he brought the axe down. The axe tears through the defiant knot, splits the log in two but the axehead buries deep into the stump as the handle explodes into pieces, destroying the axe.
From my recollection I didn't have the High Huntsman say anything, he just delivered an acknowledging glare at the irony. The PCs left defeated. The cost of the lost Skill Challenge was that the mass battle to end the tier was + 1 level in difficulty in encounter budgeting. Because of the way of this loss, I actually had the Half-Orc High Huntsman cut a deal with the Horde, in return for sparing his people/lodge, his Rangers showed the horde's lead scouts a secret mountain path (cue Thermopylae) that let them surround the manned bastion that spanned the gap. The PCs knew who their betrayer was immediately and after defeating the horde (with great cost...almost all of the Rangers of the other lodges were killed), conflict with that rogue lodge ensued.