This is an update to this post in which I was frustrated by my party's tendency to long rest after every single encounter to get all their stuff back. I had so many replies that I couldn't hope to reply to all of them, and I just finished my latest session with the insights I gained there, so I thought I'd give an update. I flaired it as "offering advice" since I'm sharing my own experience, and linking to a thread with a ton of great advice in the comments.
Firstly, thank you to everyone for the replies. I hadn't done my due diligence as a DM in a few key ways, namely by not fully understanding the rules regarding long rests. I learned that a party can only benefit from a long rest once every 24 hours, and that it has to be a period of a reasonable amount of restfulness (i.e. in handcuffs might not be the best place to sleep for eight hours and wake up perfectly rested and refreshed). I've also just generally not been as strict in enforcing the difficulty of my campaign, and I need to work on my confidence as far as encounter-building goes.
Now, as for how the session went. After the encounter and loot they got at the end of our last session, the party traveled back to the inn and did the only long rest they got the entire session. After their long rest, they went and did their first fight, a gladiator-style arena battle against two mindwitnesses, and while they came out on top our ranger and paladin both came out a little worse for wear. Almost immediately after leaving the arena I introduced an urgent new objective when a boy ran up and told them about his missing friend, whom he'd last seen going to an area that previously two PCs had discovered had a nasty smell to it. They go and check it out, and a fight against two spawns of Kyuss ensues–one that had been rotting for some time, and the other the corpse of the boy they'd been sent to find.
A second fight really brought our paladin to the brink–he almost went down when a worm burrowed its way in his skin and started hammering him with necrotic damage–but honestly? I'm really happy with how it went. The party had to be smarter about using their resources, and I also got the chance to introduce a sense of urgency that has been lacking–they didn't fully investigate the area where the spawns of Kyuss were, so there were consequences and a villager died for it, plus they had another, decently dangerous fight fairly immediately after the last.
TL;DR: I'm starting to learn how to pace sessions better, and managed to introduce some much-needed urgency to my session so that my players have to play a little smarter. Thanks everyone!
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