Well we had a couple of really fun (hysterical, really) combats this week, and the initiative (or lack of it) has been working very well the last couple of weeks.
The first encounter was following some tiny tracks in the snow away from their horses that had been looted in the night. The tracks ended, but they eventually found a bag hanging up in the trees. While trying to get that down, one of them was stabbed in the backside by a previously invisible sprite.
After being on the wrong end of a few snowballs (including a critical hit!), and other pranks, two of them were fed up. The bard backed away from the party and hoped to catch the invisible pranksters in a Thunderwave. She got one, which instantly dropped into the snow. Dead. The ranger and assassin quickly (and successfully) attempted to stabilize and heal it.
In the meantime, the rogue decided to go on the offensive. While he's about to make his attack, the ranger and assassin are yelling at him to stop, and both attempted to tackle him, but failed miserably (I think they rolled a 2 and a 3). In the meantime, the first attack roll was a 20, but since the sprite was invisible and (thankfully) the attack was with disadvantage. He still hit, but somehow rolled a 1 for damage, and the other two were once again able to save the poor creature.
In the meantime, the bard decided to listen to the other two and end the fight by casting sleep. Now the current rules don't indicate that sprites are immune to sleep, but being fey creatures, and the rest of the party being elves except the bard and the rogue she ended up putting the rogue to sleep. The sprites peppered him with a few arrows and flew away.
Just prior to the combat itself, the other bard (a sylvan elf) had disappeared into the snow using his natural hiding ability (rolled a 20 actually), this was after the sprites had dropped his trousers.
But the transition from encounter to combat and back was seamless, and the only time that an initiative roll might have been needed was when the ranger and assassin were attempting to tackle the rogue. It became irrelevant when they rolled so low so no initiative (reaction) roll was made.
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An interlude occurred when they noticed a displacer beast stalking them from the hills. It was still far enough away that they could have attacked with ranged spells, but instead they opted to try to avoid combat. The ranger is particularly fond of his bag of tricks, and pulled a giant badger out of it this time. So he sent the badger off to investigate the displacer beast (it didn't last long, but delayed it a bit), and in the meantime they took off at a fair pace. Riding horses with a speed of 60' and the beast only 40' and a snack. Even with the snow slowing all of them down it was a good choice.
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The second major encounter was at night. They had decided to continue travelling (on horseback) since it's nearly a full moon and the reflection on the snow on the largely open terrain provided plenty of light. Or so they thought. They are travelling along the edge of the Forlorn Hills, and did not see the wyvern crouching on the hillside until it was nearly too late.
On the first diving pass the wyvern missed (3 and a 4), and in the process of turning around took a few good hits from the ranger. In the meantime the assassin was herding the merchants they were protecting off of the road, the rogue (arcane trickster) hit it with a flame bolt, the human bard dropped off her horse into the snow to play dead, and the sylvan bard started to play his pipes of haunting.
When the wyvern came back around it grabbed the human bard's horse (randomly). In the meantime it made its save against the pipes, the ranger was firing more arrows at it, the human bard was watching her horse be snatched above her, the assassin was still herding merchants, and...
So I was ready with my description of the beast flying up out of reach in the hills to munch on the horse, also giving them the opportunity to get away. Hey, it's a tough creature and it was late.
The rogue decided to use his rope of entanglement.
What?!?
OK, does it work against a large creature? No restriction listed in the description. Looked at the d20 wyvern - 15' long, 20' wingspan, and a 30' rope. OK I think, maybe he'll get a leg and I'll get to yank him out of the saddle.
Nope. The wyvern attempted his Dexterity save to avoid it. A freaking natural 1. So, with no rules specifically against it, and that roll, yep he entangled the diving wyvern, just as it was grabbing the horse.
So the thing crash lands, restrained, and the group falls on it with advantage to attack (yes, with two rogues, one of them being an assassin), and that's the end of the wyvern (and the horse, unfortunately).
Again, everybody just told me what they were doing, and everything was either simultaneous or logically ordered. There wasn't really any point where initiative would have mattered. The only point where I think it might have made a difference would be if he entangled the wyvern before it grabbed the horse, but that was pretty much the place where the wyvern was in range anyway. Even if it had been entangled first, it would have just barreled through the poor horse anyway.
And like the encounter with the sprites, it was just part of the continuous story, no hard transition between exploration and combat.
Ilbranteloth