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Message: <blockquote data-quote="Ilbranteloth" data-source="post: 7208114" data-attributes="member: 6778044">Even at that level and with magic, it can still be a very interesting session if you run it like a dungeon. Set decision points (rooms) from 30 to maybe 300 feet apart. Remember that not all of the movement will be vertical, which can also extend the climb. For example:You've made it about 300 feet up, where the cliff juts out about 20 feet. It's about 30 feet to the left, or 80 feet to the right to get around it, or you can try to climb the overhang. An Insight check (in my case passive, to start), would tell them that the easiest route is to the right, but they can't easily see what's beyond that point. The left is harder, but it looks like there is a good path beyond that with a vertical crack in a bit of a corner making the vertical ascent a good probability there. Climbing the overhang is the shortest, but by far the most difficult.You then have encounters or events at each point. For example, to the right, there is a further overhang, and fewer handholds once they get around the corner. Not the best option. To the left, there is a clutch of stirges nesting in the vertical crack. If they are moving half-speed and using Stealth, they might be able to detect the stirges before they awaken them. Going over the overhang is very difficult, but if successful, it's shorter, and there's a very easy climb for several hundred feet. Although things like harnesses, carabiners, and such didn't exist, I'd assume they can use pitons and rope to attach themselves to the cliff. They won't have 1,300 feet of it, so if somebody falls, there will be a second skill check to see if the next person is also pulled off of the cliff, and once it gets to the pitons, it would be a check to see if it pulls loose (with it being more likely if more people fell). If somebody does fall (and use feather fall), then you can assume they'll take the same route up that they did the first time, to rejoin their companions. Just make the climbing checks that you feel are necessary, but let them rejoin fairly quickly. Instead, keep track of the amount of time it took, since their potions have a limited time limit. Combats should involve lots of flying creatures that can dive to attack then get out of reach, the characters can only use one hand, and risk falling each time they make an attack. Things like stirges are great. With a half dozen attacking a single target, they can't all easily be killed in the first round. So they'll have the opportunity to cause damage for a couple of rounds.Design rockslides, loose rocks, and even encounters with relatively insignificant creatures as traps. For example, a flock of birds might cause a small amount of damage, but force a climb check with disadvantage or fall.Keeping track of time will be important. Figure out blocks of time before the session. The easiest approach would be to pick a set amount of time, such as 5 minutes, for each decision point, regardless of what happens at each one. That means a potion would last 12 decision points. For ability checks themselves, instead of making them every 50', make them between decision points, and apply modifiers based on the distance. So the base DC might be 15, but because you're climbing 300' to the next point, make it a DC 18 or 20.This is based on the assumption that they'll need to set a piton and attach a rope, detach a rope from the back and maybe remove the piton, then move forward 50' and do it again. They could potentially tie multiple ropes together, but that runs the risk of longer falls for more damage, and the knot between the two failing on a fall.On a fall not lessened by feather fall but stopped by a rope, I would probably make a check to possibly drop equipment.I would also use the encumbrance rules (although RAW it would only impose disadvantage on climb checks if you were heavily encumbered), and probably also impose disadvantage on climb checks in any armor that has a strength requirement. But if I didn't impose disadvantage for merely being encumbered, there would be a greater chance that your equipment could pose a problem on a failure.If there is a failure, pick a random point along the way and that's a new decision point (adding 5 minutes of time), and address the failure.There are a lot of other options for failure (dropping something, getting equipment hung up on something, a piton pulling loose and you have to decide if you go back to fix it, or potentially risk losing it, knocking rocks loose, attracting curious creatures, or attacks from those at the top of the cliff, etc.). Not all of them have to cause damage either. They should be suspenseful, though, require some sort of action on the part of one or more of the PCs, and is eating up time. I generally use the threshold of failing by 5 or more is worse than 4 or less.Many of the possibilities for failure could also be potential random encounters. If you don't want "disturbing a bird's nest" to be a possible result on a climb check failure, then check for random encounters in addition to the climb check between points. It should be pretty clear to the character that can fly, that unless they have some other alternative (rope trick, for example), they won't be able to rest until they reach the top, and they'll be able to use that ability once on the climb.</blockquote>

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