On Initiative

Initiative is a system that's always bothered me in D&D. There are tons of way to determine it throughout D&D's history, from Chainmail to B/X to AD&D to what exists in modern editions of D&D. There are things I enjoy about all of these systems - pass-through fire, the elegance of B/X, weapon speeds, casting times, and the chance of spellcasters being interrupted in AD&D, and the simplicity of 5e - but none of them quite "do it" for me.

I'm currently running an AD&D 2e campaign, and expressed some concerns early on about the initiative system using weapon speed factors and casting times. Admittedly, we haven't had a ton of complex combats yet (after nearly ten sessions!), but I've warmed up to the system. I usually have players declare actions at the start of combat, roll initiative accordingly, and then we only reroll when someone wants to do something different than they did the previous round.

After my AD&D game ends - which might take years, based on my last campaign with this group - I'm hoping to run Old School Essentials (using the Advanced Fantasy rules, if Exalted Funeral ever restocks the Advanced Fantasy Player's Tome, that is). OSE uses the B/X initiative system, which, like with AD&D, I'll likely try to run unmodified for as long as it doesn't bother me too much, so I can feel like I'm having the intended experience.

For now, I want to talk about initiative in 5e. By the book (PHB, page 189), initiative is determined by each creature in combat making a Dexterity check. Then, combat is resolved in descending order based on the results of each creature's check. Some character classes get an additional bonus to their initiative check - the Champion fighter adds half their proficiency bonus at 7th-level, the Gloomstalker ranger adds their Wisdom modifier at 3rd-level, and the Swashbuckler rogue adds their Charisma modifier at 3rd-level, for example.

Some players have a problem with this, as rolling a die, adding a number, writing down the total, and reordering the totals into an descending list is seen as onerous. I play entirely online at this point using Roll20, so the turn tracker makes this a lot easier, and I don't see it as a problem. If I was playing in person, I'd just ask one of the players to track initiative.

Still, one could always simplify 5e initiative by using old-school side-based initiative. This is even suggested as an optional rule in the 5e DMG (page 270). One benefit of this system is that it allows players to better coordinate their actions, emphasizing teamwork. A drawback is that it accentuates the "rocket tag" nature of 5e combat - the side that goes first is, in all likelihood, going to devastate the other side before they get a chance to act.

I'm growing to enjoy the more complex nature of initiative in AD&D. If anything - as with many elements of 5e - my inclination is to make 5e initiative more complex.

Declarations, Simultaneity, and Speed of Action

Initiative in 5e is truly turn-based - that is, actions aren't occurring simultaneously. A character or monster waits around until it's their turn, at which point they take all of their actions all at once - interrupted only by the occasional reaction - then the next person goes. One drawback of this is that players often don't decide - or even think about - what to do until their turn comes up, which often slows the combat to a standstill. 

I prefer that actions are declared at the start of the round, then resolved somewhat logically in order, while occurring simultaneously in the fiction. This has the added benefit of allowing spellcasters to be interrupted while casting. Since they have to declare whether or not they're casting a spell at the top of the round, they start casting immediately. If they're hit before their turn comes around - at which point the spell goes off - they may lose the spell. This is an important balancing factor which checks the otherwise outsized power of spellcasters.

Initiative in 5e also doesn't account for what actions are being taken. A character can do nothing but move one round, then move, take a bonus action, and cast a 9th-level spell the next round, and it takes the same amount of time. It doesn't matter if the character is using a heavy weapon, a light weapon, a loading weapon, or a reach weapon - so long as they rolled high enough, they go next.

5e has another optional initiative rule for speed factor, similar to AD&D (DMG, page 170). Light weapons and smaller-than-medium creatures are faster, and heavy weapons, loading weapons, two-handed weapons, and larger-than-medium creatures are slower. I don't really want to modify every initiative roll every round, however.

Taking Initiative

Inspired by a combination of B/X's elegance, AD&D's use of speed factor, and 5e's own suggestions of speed factor modifiers, I've come up with personal house rules for initiative in 5e. The exact order of operations differs somewhat from B/X where my own sensibilities and preferences are at odds with those rules.

The important thing to note is that players and monsters still roll for initiative at the start of combat. It's important to me to preserve this element of initiative in 5e so that those classes which benefit from bonuses to initiative do not then lose out on those class features. The initiative score is used only to resolve ties within the following sequence, which plays out in order each round:

1. Check monster and NPC morale: This obviously requires a system for checking morale.
2. Declare actions, spellcasters begin casting: AD&D suggests that the DM does not telegraph the monsters' intended actions to the players, but I disagree on this point. Telegraphing the monsters' actions allows players to make informed choices. If the monsters look like they will flee, the players can decide whether to pursue or simply let combat end. If an enemy spellcaster begins casting, the players can focus-fire the caster to attempt to interrupt the spell. If it looks like the goblins are moving to attack the cleric who desperately needs to heal the wizard, the fighter can move to intercept them. The general type of action is what's important, not the specific target of an attack or spell or the destination of movement. If a character declares that they're attacking with their bow, but their target is dead or out of range when missile attacks come up in the initiative order, they can choose another target. If the spellcaster prepares a fireball, but a melee forms before the spell goes off, the caster can later aim the fireball such that it causes less harm to their allies.
1. Spellcasters who take damage must make a Constitution saving throw (PHB, page 203) or lose their spell: The spell fizzles, and the spell slot is lost.
3. Bonus actions: These go off first, unless they have a specific trigger which wouldn't occur until later (for example, a character who uses two-weapon fighting makes an off-hand attack after the main hand attack, and a monk uses Flurry of Blows after taking the attack action). Otherwise, these are resolved in order following the standard initiative system below (for example, a rogue can dash, disengage, or hide as a bonus action before a wizard can cast misty step as a bonus action). I allow creatures to drink a potion as a bonus action, so that would also go here.
4. Magic item activation: My inclination is that these should be faster than regular attacks and spellcasting, as they normally require only a command word or press of a button to activate.
1. Scrolls go on spellcasting: Because they're just a means of casting spells.
5. Missile attacks: These go off first to represent that ranged attackers have arrows knocked, bolts loaded, thrown weapons ready, etc. This allows ranged attackers to attack before their targets take cover, and before a big melee forms, at which point they may have to fire past other creatures or risk hitting their allies. Beyond the first round of combat, this obviously becomes more complicated as the scenario unfolds. Missiles attacks, in turn, are resolved in the following order (ties are resolved by initiative order):
1. Finesse and light weapons: Thrown daggers, darts, hand axes, and light hammers.
2. Non-finesse, heavy, light, loading, and two-handed weapons: Javelins, nets, slings, spears, and tridents.
3. Heavy, loading, and two-handed weapons: Blowguns, bows, and crossbows.
6. Movement and non-attack/spellcasting actions: Now characters and monsters can move into or away from melee, seek cover against further missile fire, and the like. I'm tempted to further restrict spellcasters by ruling that they can't move on a turn where they're also casting a spell (which comes from B/X), but in wanting to preserve 5e's conception of highly-mobile spellcasters, I'm resisting the urge here. Here, using initiative order is absolutely necessary, or else everyone simply moves in somewhat disparate directions (the melee fighter moves towards the goblin archer, who in turn moves away, meaning no ground is gained at all), unless the two sides are like-minded about closing into melee range. This is also where characters can open doors, switch weapons, and otherwise interact with objects, attempt to hide (if not using a bonus action to do so), and the like.
1. Regular movement occurs first
2. Dash actions occur last
7. Melee attacks: This comes after movement by necessity. Melee attack are resolved in the following order (ties are resolved by initiative order):
1. Reach weapons of all kinds: Glaives, halberds, lances, pikes, and whips. A lot of these are heavy weapons, which come later in the order, but it only makes sense to me that these should strike first, due to their longer reach. I'm a bit divided on whips being here, but whatever. No one uses a whip anyway.
1. Characters and monsters with the longest reach go first: A bugbear character with +5 feet of reach wielding a glaive attacks before a human wielding a glaive. A roper with a 50-foor reach attacks before just about everyone. 
2. If reach is equal, resolve actions in the order used for other melee attacks: Tiny monsters using natural weapons go first, then whips and small monsters using natural weapons, then lances and medium monsters using natural weapons, then glaives, halberds, pikes, and large monsters using natural weapons, then huge monsters using natural weapons, then gargantuan monsters using natural weapons.
2. Tiny monsters using natural weapons: The will-o'-wisp's shock attack is faster than a dagger.
3. Finesse and light weapons, and small monsters using natural weapons: Clubs, daggers, hand axes, light hammers, rapiers, scimitars, shortswords, and sickles. The twig blights claws are as fast as a dagger. 
4. Non-finesse, heavy, light, reach, and two-handed weapons, and medium monsters using natural weapons: Flails, javelins, maces, morningstars, spears, war picks, and battleaxes, longswords, quarterstaffs, spears, tridents, and warhammers wielded with one hand. A mind flayer's tentacles are as fast as a longsword.
5. Heavy and two-handed weapons, and large monsters using natural weapons: Greatclubs, greataxes, greatswords, mauls, and battleaxes, longswords, quarterstaffs, spears, tridents, and warhammers wielded with two hands. A yeti's claws are as fast as a greataxe.
6. Huge monsters using natural weapons: A giant elk takes a few second to rear up and kick with its hooves.
7. Gargantuan monsters using natural weapons: A rock swoops down and rakes with its talons.
8. Spells: It's important that these go close to last, as I like the idea that spells take longer to cast than most other action in combat. It also provides ample time to interrupt or slay spellcasters with attacks, which is an important balancing factor. It makes it harder to cast fireball, lightning bolt, and cone of cold in an ideal spot without causing collateral damage to allies. 
1. Spellcasting is resolved in ascending order based on the level of the spell, such that 1st-level spells go off first, and 9th-level spells go off last. The wizard can fire off a magic missile before another wizard casts time stop. Otherwise, ties are resolved by initiative order.
9. Breath weapons and other special monster abilities: These go last purely as a matter of taste. I like the idea of a dragon "charging" its breath weapon and unleashing it at the end of the round. It gives players time to react, such as by killing the dragon before it attacks or by taking cover. In AD&D, breath weapons actually have a smaller initiative modifier (i.e., they are faster) than a dagger, so one could also put this near the top of the turn order if desired.
1. Larger monsters go later: Like with melee attacks with natural weapons, so a young dragon unleashes its breath weapon before an ancient one, for example.

A final important note is that creatures can choose to take any of the above actions during a later stage of the initiative order than listed. So a character can take a bonus action after activating a magic item, make a missile attack after moving, or make a melee attack after casting a spell, for example. 

They character is essentially delaying these actions until later in the round if they're for whatever reason unable or unwilling to take that action when they're otherwise supposed to. Granted, I suppose a player could choose to delay their entire turn until the end of the round, taking all of their actions at once, but the drawback would be essentially granting initiative to their enemies, so maybe that isn't a problem.

Here is the order of operations sans my commentary:

1. Check monster and NPC morale
2. Declare actions, spellcasters begin casting
1. Spellcasters who take damage must make a Constitution saving throw or lose their spell
3. Bonus actions (unless triggered by another action later in the initiative order)
1. Resolve the order of bonus actions based on the type of action (i.e. magic item activation, movement, spellcasting, etc.)
4. Magic item activation
1. Scrolls go on spellcasting
5. Missile attacks: 
1. Finesse and light weapons
2. Non-finesse, heavy, light, loading, and two-handed weapons
3. Heavy, loading, and two-handed weapons
6. Movement and non-attack/spellcasting actions
1. Regular movement occurs first
2. Dash actions occur last
7. Melee attacks:
1. Reach weapons of all kinds
1. Characters and monsters with the longest reach go first
2. If reach is equal, resolve actions in the order used for other melee attacks
2. Tiny monsters using natural weapons
3. Finesse and light weapons, and small monsters using natural weapons
4. Non-finesse, heavy, light, reach, and two-handed weapons, and medium monsters using natural weapons
5. Heavy and two-handed weapons, and large monsters using natural weapons
6. Huge monsters using natural weapons
7. Gargantuan monsters using natural weapons
8. Spells
1. Spellcasting is resolved in ascending order based on the level of the spell (i.e. 1st-level spells first, 9th-level spells last)
9. Breath weapons and other special monster abilities
1. Resolve order based on monster size (i.e. tiny first, gargantuan last)

It's worth noting that I'm not currently running a 5e game, so these rules are not playtested. I'm sure they are in need of some refinement, and there are likely edge-cases which I'm neglecting, but this is a theoretical framework from which I'll work the next time I DM a 5e game.

Quick Thinking, Sage Advice

One thing which still bothers me is that Dexterity is used to determine initiative regardless of the action being taken. It makes more sense to me that spellcasters would use their spellcasting ability modifier instead, if they're casting a spell. My inclination in that case would be for spellcasters to reroll their initiative each round if they're switching between casting spells and taking more physical actions - or else just modify their initiative by the difference between their Dexterity and their spellcasting ability as needed - but that kind of rerolling/fiddling is the sort of thing I'd like to avoid. Plus, again, I use Roll20, and as of now there isn't an option to change the ability score which modifies the initiative roll, so this seems like more trouble than it's worth.

5e's designers have even suggested using Intelligence for initiative instead of Dexterity, and this is a popular house rule I've seen here and there. However, it doesn't really solve the problem I have, which is that initiative isn't being determined by the action being taken, just whichever ability score is higher for the specific character or creature.

Ultimately, like many of my house rules, this won't be for everyone. It is likely more complex than many people prefer, with players and DMs needing to keep track of who took what actions over the course of a round - more than they normally would have to, but I crave more complexity in my 5e games, and specifically in the case of initiative. 

This process may exacerbate the issue of initiative slowing the game down, but my hope is that the combination of declared and simultaneous actions, along with a quick outline of the order in which these actions are resolved, will actually reduce time spent on individual players' turns, and make combat feel more lifelike and fluid, rather than artificially turn-based, playing out in sudden starts and long, drawn-out stops.