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Message: <blockquote data-quote="Quickleaf" data-source="post: 8380065" data-attributes="member: 20323">Sounds like this is a case of wanting to goad the other side into initiating hostilities? I'd actually need to know how each side (drow & PCs) intend to to do that – will it just be through roleplaying (e.g. leveraging known bonds/ideals/flaws or insult-slinging) or does someone intend to use magic (e.g. crown of madness)? In the former case, I'd let it play out until the breaking point and someone decides to attack, then roll initiative as normal. In the latter, I'd be inclined to roll initiative unless they had the Subtle Spell metamagic.This would not be a case of Insight vs Deception, IMHO, because everyone is on high alert,  suspicious of the other side, and anticipating a breakdown in negotiations, and also no one has declared intent to deceive the other side.The assassin is going to have to play smart to reach the target...<ul> <li data-xf-list-type="ul">Cast silence on the door before picking the lock, or maaaybe using some kind of metal-dissolving acid that doesn't make noise.</li> <li data-xf-list-type="ul">Use scry + teleport tactics or other spells/magic to get inside.</li> <li data-xf-list-type="ul">Disguise themself as someone who is supposed to bypass the locked door, for example, to deliver food to the prisoner once a day or an official come to perform a followup interrogation.</li> <li data-xf-list-type="ul">Orchestrate a "lapse in the prison defenses" or even a "masse jailbreak" to lure the target into attempting escape... right into an exposed position where the assassin wants them.</li> <li data-xf-list-type="ul">Slip sticks of burnt othur fumes incense under the tiniest gap beneath the door and try to kill the target with poison gas.</li> </ul>Like in the above situation, the target needs to play smart...<ul> <li data-xf-list-type="ul">Pay off or blackmail a guard to keep him informed of anyone suspicious entering the prison.</li> <li data-xf-list-type="ul">Use magic like clairvoyance or arcane eye.</li> <li data-xf-list-type="ul">Send their familiar (or other invisible animal companion / conjured critter / homunculus / pet) to scout the main hall/area leading to their prison cell.</li> <li data-xf-list-type="ul">Rig some kind of a simple "bucket trap" on the door to make a bunch of noise (or potentially even splash rock dust/chalk on invisible intruders) when the door is opened.</li> <li data-xf-list-type="ul">Getting a message out of the prison to circulate among local crime guilds that he'll pay twice the contract on his head to not be killed.</li> </ul>Unless there are further details, this one is a pretty straightforward group Dexterity (Stealth) check opposed by the orcs' passive Perception. If half or more of the PCs succeed, then they collectively surprise the orcs in the ravine.It's also entirely possible that certain players may have creative ideas, spells, or class abilities that they want to draw upon in order to ambush the orcs. In that case, I arbitrate those on a case by case basis – some may be narrative fluff, others might grant advantage, and others might allow them to auto-succeed. It depends on the resources expended, the player's idea, and the specific details of the scenario.The PC rogue needs to do some advance planning. If this was impromptu, there would be no "quick getaway" – there would be an edge-of-your-seat chase scene, where I'd rely on my <a href="https://www.enworld.org/threads/making-chase-rules-that-actually-do-what-theyre-supposed-to.482668/" target="_blank">rewrite of the 5e chase rules.</a>Some things the rogue might do to set things up for a quick getaway might include...<ul> <li data-xf-list-type="ul">Dosing the stew at the city guard's barracks with a long-acting lethargy-inducing poison.</li> <li data-xf-list-type="ul">Paying off some kids to drop marbles or caltrops when the mean bodyguards are in pursuit.</li> <li data-xf-list-type="ul">Learning that the local temple of Tymora has a procession to vespers during the politician's time at the agora, and having garments created which can quickly make them blend into the temple robes worn by the priests of Tymora.</li> <li data-xf-list-type="ul">Having an ally pre-cast longstrider, pass without trace, nondetection, or similar spells.</li> </ul></blockquote>

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