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As a Dungeon Master, one of my jobs is to adjudicate the rules of the game at my table. I can honestly say that no single rule in D&D gives me more of a headache than Sneak Attack. It's not that the rule is complicated (though the number of options have increased with the release of the Sword Coast Adventurers Guide), but rather that people bring a lot of preconceptions into their understanding of Sneak Attack, often borrowing from earlier editions that don't really apply in Fifth Edition terms.

The best way to cover those misconceptions is to break down the actual Sneak Attack rule, pointing out where people seem to get things wrong.

Once per turn, you can deal an extra 1d6 damage to one creature you hit with an attack if you have advantage on the attack roll.

Let's begin with one that should be obvious: Sneak Attack does not give you advantage on your attack roll. I've had two different players claim that they were using Sneak Attack to gain advantage on their attack roll, and that just doesn't make sense -- you need advantage before you can use Sneak Attack (but see below).

In addition, though this isn't as prevalent, if a character has more than one attack per turn, only one successful attack during that turn can deal Sneak Attack damage. Since rogues don't get the Extra Attacks feature, this only occurs with multi-classed characters, usually ranger/rogues or fighter/rogues. And though this does allow a rogue to deal Sneak Attack damage again if he makes an attack when it isn't his turn, every method for doing so currently in 5E D&D requires the character to use his reaction, which is only usable once between turns. So if you have a character who is using Extra Attacks, Action Surge, or Haste to deal multiple instances of Sneak Attack during the same turn, that's wrong. Note that, because the rule specifies that the character has to hit to deal the extra damage, a character with multiple attacks does not need to declare Sneak Attack prior to the attack roll; declaring after a successful hit is sufficient, but once declared, the character cannot change that declaration.

Lastly, since Sneak Attack damage is expressed in dice, they are multiplied on a critical hit. However, if a fighter/rogue has already dealt Sneak Attack and then rolls a critical hit on a subsequent attack, it is too late to go back and declare the crit as the Sneak Attack.

The attack must use a finesse or a ranged weapon.

Note that the definition of 'ranged weapon' is not 'a weapon that can be used to make ranged attacks'; in 5E, a 'ranged weapon' is a weapon listed as a ranged weapon on the weapon tables. Thus, javelins, spears, hand-axes, light hammers, and tridents cannot be used to make Sneak Attacks, even though they can be used to make ranged attacks -- they are all listed as melee weapons on the weapon charts.

The following are ranged weapons, by the definition of 5E D&D:

Light Crossbow

Dart

Shortbow

Sling

Blowgun

Hand Crossbow

Heavy Crossbow

Longbow

Although the net is also a ranged weapon, it cannot be used to Sneak Attack -- the net deals no damage, and thus there is no way to apply the 'extra' damage from the Sneak Attack to it. (Some players may argue that you can add damage to zero, but that is effectively a ruling from Third Edition, not Fifth -- in 5E, the net doesn't deal zero damage, it deals no damage, and thus can't do extra damage when it deals no damage to begin with.)

The dagger, however, can be used to make sneak attacks, as it is a finesse weapon. The following are finesse weapons, since they contain the finesse property in the weapon list:

Dagger

Dart

Rapier

Scimitar

Shortsword

Whip

Note that, because being a ranged weapon is defined by the weapon chart and not by the mode of attack used with the weapon, finesse weapons like the dagger can still benefit from Sneak Attack when used to make ranged attacks. Likewise, a ranged weapon used to make a melee attack (typically as an improvised melee weapon) can benefit from Sneak Attack. Nothing in the rule for Sneak Attack requires the rogue to use a weapon with which he is proficient, nor use it in a specific manner.

Single-classed rogues can effectively use Sneak Attack with any allowed weapon, but multi-classed rogues will almost always choose rapier as their weapon of choice, since it has the highest base damage. (Multi-classed rogues with the Crossbow Expert feat might choose to use the heavy crossbow instead, as long as they are at least Medium size.)

Now things start to get tricky:

You don't need advantage on the attack roll if another enemy of the target is within 5 feet of it, that enemy isn't incapacitated, and you don't have disadvantage on the attack roll.

There are a couple of potential 'gotchas' in here that I've messed up myself as a DM that should be pointed out.

First, though most D&D combats take place between only two sides, Sneak Attack does not require that the creature within 5 feet of your target be your ally -- only that it be an enemy of the creature you are attacking. (This can be significant if there are 'non-combatants' in the combat as well -- do they count as enemies of your target? If so, you can use them to Sneak Attack, if not, you can't.)

In addition, the restriction that you don't have disadvantage on the attack roll is not a general prohibition against using Sneak Attack while having disadvantage. It's actually true that having disadvantage will prevent you from making Sneak Attack by using advantage:

If circumstances cause a roll to have both advantage and disadvantage, you are considered to have neither of them...

So, if something applies disadvantage to your attack roll, you cannot have advantage on that roll at the same time, and thus the rule that allows you to Sneak Attack when you have advantage doesn't apply. However, note that in this situation, you are also not considered to actually have disadvantage on the roll either, so if your target has an active enemy within 5 feet of it, you still get to apply your Sneak Attack, if you hit.

Lastly, note that nothing in the rule for Sneak Attack mentions 'reach' or 'threatened areas' -- the latter is another rule carried over from previous editions of D&D -- the creature enabling Sneak Attack must be within 5 feet of your target for you to be able to claim the Sneak Attack benefit from it, so Polearm Masters and mounted lancers won't always be your friends.

In addition to the above, the Swashbuckler archetype adds yet another qualification for Sneak Attack, as part of the Rakish Audacity ability.

In addition, you don't need advantage on your attack roll to use your Sneak Attack if no creature other than your target is within 5 feet of you. All the other rules for the Sneak Attack class feature still apply to you.

Note that the restriction is on you -- as long as creatures aren't within 5 feet of you, there can be as many creatures within 5 feet of your target as can fit and you can still take your Sneak Attack.

The 'all other rules still apply' text means that, even if you have an adjacent ally and thus can't use the special Swashbuckler feature, you can still Sneak Attack by having an enemy of the target within 5 feet and not having disadvantage. The Swashbuckler feature is in addition to, not in place of, the general conditions for Sneak Attack in the Rogue feature.

Note as well that Swashbucklers have a harder time using ranged attacks than other rogues do -- the 'no creature other than your target' restriction means that your target does have to be within 5 feet of you in order for you to use this version of Sneak Attack. (A DM could rule that 'no creature other than your target' doesn't require the target to be within 5 feet, but other aspects of the archetype {specifically the ability to move away from a creature attacked in melee without provoking an attack of opportunity} suggest that the Swashbuckler is meant to be dealing Sneak Attack damage from melee range, not with bows or crossbows.)

Most importantly, note that the Swashbuckler feature mentions nothing about disadvantage -- this means that a Swashbuckler with disadvantage who can maneuver into a position to attack without any other creature other than the target within 5 feet can still Sneak Attack.

A lot of weapons in 5e with the Heavy property also have the Two-Handed property. Which means you can't dual wield them even with the Dual Wielder feat. - Role Player's Respite (https://roleplayersrespite.com), "Your Simple Guide to Dual Wielding in DnD 5e"

Wielding two weapons is one of those things that looks bad-ass and as a result, players often want to be able to do with their characters. However, the process of actually fighting with two weapons is something of a mixed bag for most classes, and it doesn't make it any easier that many tables get the rules for two-weapon fighting wrong, most significantly, using the rule for two-weapon fighting when it doesn't really apply.

How most characters fight with two weapons

The key rule for fighting with two weapons, for most classes, is found on page 77 of the Player's Basic Rules (or page 195 of the Player's Handbook -- the text is identical):

When you take the Attack action and attack with a light melee weapon that you're holding in one hand, you can use a bonus action to attack with a different light melee weapon that you're holding in the other hand. You don't add your ability modifier to the damage of the bonus attack, unless that modifier is negative. If either weapon has the thrown property, you can throw the weapon in stead of making a melee attack.

First off, some rules explanation. A 'light' weapon is a weapon that has the Light property on the Weapons list on page 48 of the PBR (page 149 of the PH). In fact, the description of the Light property specifically says the weapon is ideal for two-weapon fighting and references the chapter with the rule for Two-Weapon Fighting.

However, one thing folks frequently forget is that the rule also requires that you attack with a 'melee' weapon, which is a weapon listed under 'Simple Melee Weapons' or 'Martial Melee Weapons' on the same list. I have seen a number of charts of 'eligible weapons for two-weapon fighting' that include the hand crossbow (including the linked article in the introductory quote above), because the hand crossbow is a light weapon, but the hand crossbow is not eligible for the rule for two-weapon fighting because it is not a melee weapon, it is a ranged weapon, even when used to make a melee attack. (You can still effectively 'dual-wield' light crossbows, but it requires the use of the Crossbow Expert feat, which contains a variant of the Two-Weapon Fighting rule that allows you to fire a loaded hand crossbow as a bonus action after using the Attack action to attack with a light weapon; note that this variant of the rule does not specify that the initial attack be made with a melee weapon, which enables the use of the light hand crossbow to enable a second hand crossbow attack. However, there is some discussion that this may not allow you to dual-wield hand crossbows for more than a single round, as while the Crossbow Expert feat removes the Loading quality for crossbows with which you are proficient, the feat does not remove the Ammunition property of the hand crossbow, which requires a 'free hand' to reload the crossbow after firing. Holding a hand crossbow in each hand prevents those hands from being considered 'free', based on a similar wording in the spellcasting rules for which the War Caster feat serves as an exception.)

The rule also points out that you use your bonus action to attack with a 'different light melee weapon that you are holding in the other hand', but this does not require that you be using two different kinds of weapons -- you can in fact dual-wield with two daggers, or two scimitars, or two of any identical light weapon, so long as you are actually holding two of them, one in each hand. (The rule effectively prohibits wielding one weapon and simply moving it to your other hand to qualify for the second attack.) In addition, if you have a positive Strength modifier that you would normally add to your weapon damage roll, you do not add this modifier to your damage for your bonus attack. (There are a few other implied restrictions, which we'll cover later when we talk about the rules that allow you to ignore them.)

Note as well that light weapons tend to do less damage than non-light weapons; there is no light weapon on the basic weapon list that deals more than a d6 of damage, while there are a number of 'two-handed' and/or 'heavy' weapons that can deal significantly more than that. This might make some players believe that two-weapon fighting isn't as effective as fighting with one big weapon, but in fact the rules are designed to try to equalize those situations as much as possible for most 'typical' characters. So, for example, say you have two characters with the same Strength score, one of whom is wielding a greatsword while the other is wielding two shortswords. The greatsword wielder will attack once, dealing 2d6+Str damage, while the two-shortsword wielder will attack twice, dealing a total of 1d6+Str+1d6 if she hits with both attacks. This sets up the basic mechanical difference between the two types of fighting: a 'normal' fighter will sometimes miss with a single attack, resulting in no damage, while the dual-wielder, while they will only reach the expected damage of the greatsword fighter if they hit with both attacks, will more frequently hit with at least one attack, resulting in at least some damage.

If you choose to go down the munchkin path, be aware that most optimization sources come to the conclusion that, with the appropriate feats and class options in place, two-weapon fighting is slightly better than great-weapon fighting at low levels, but great-weapon fighting becomes more effective at higher levels, for reasons we're not going to cover in this article. Just be aware that the rule we've already covered applies to all characters, regardless of class, so technically, anybody can fight with two weapons!

How Fighters and Rangers dual-wield

However, as you might expect, some classes are designed to be more effective at fighting with two weapons than others. For the Fighter and Ranger, this comes from the Fighting Style feature that the Fighter gets at level 1 and the Ranger gets at level 2. In each class, one of the options for Fighting Style is this one:

Two-Weapon Fighting When you engage in two-weapon fighting, you can add your ability modifier to the damage of the second attack.

This may seem like a fairly tame benefit, but for most low-level characters, not only is this a great bonus, but is the main effect that causes two-weapon fighting to be better than great-weapon fighting at low level. Recall our two-shortsword versus greatsword character from above; if the two-shortsword character has taken the Two-Weapon Fighting fighting style, now that character always does 1d6+Str damage on a hit, regardless of which attack hits, and does 2d6+(Str*2) damage when hitting with both attacks. Since melee fighters tend to have high Strength scores, this means that the two-shortsword character now expects to do more damage overall than the greatsword character.

You may notice that I didn't mention Paladins in this section, even though Paladins also have a Fighting Style class feature; this is because Paladins do not get Two-Weapon Fighting as an option in their class feature. This doesn't mean that Paladins can't do two-weapon fighting, but it does mean that they would need to take a level of Fighter or two levels of Ranger to get the Fighting Style feature, if it's important to them.

Notice as well that I didn't mention Barbarians in this section; Barbarians don't even get a Fighting Style option (at least none of the archetypes in the Player's Handbook do), so they do not have the option to take a Fighting Style without multi-classing, either.

How Monks dual-wield

Here's the next part of two-weapon fighting where people tend to do the rule wrong. Even experienced players can get this one wrong, as Cody of Taking20 does in his video essay on "Absolute Worst Dungeons and Dragons 5e Rules as Written". Cody wants to hate on the Two-Weapon Fighting rule because you can't use it with unarmed strikes. The rule could not be more explicit (on p.76 of the PBR, p. of the PH):

Instead of using a weapon to make a melee weapon attack, you can use an unarmed strike: a punch, kick, head-butt, or similar forceful blow (none of which count as weapons).

Since the rule for Two-Weapon Fighting above only applies when you make an attack with a light melee weapon, you don't get to use it when making an unarmed strike, since an unarmed strike is not a weapon. In addition, since the rule specifies that you make the bonus action attack with a weapon that you are wielding in your other hand, and an unarmed strike is not a weapon, you cannot make an unarmed strike using the bonus action attack enabled by this rule. Cody may have a point when complaining that bar-brawler type characters can't take advantage of this rule, but he's completely wrong when he complains that monks can't use this rule. Well, he's not wrong that monks can't use this rule, but the point is that monks don't need to use this rule: monks in fact have two different class-specific ways to effectively dual-wield without making use of this rule, both of which are at least as effective if not more effective than this rule.

First, monks have access to the Martial Arts ability at level 1, which resembles the rule for two-weapon fighting quite a bit; a monk has to use a 'monk weapon' which is defined as a shortsword or a simple weapon that doesn't have either the heavy or two-handed properties. The monk can also explicitly use unarmed strikes, as per the text of the rule. When the monk uses the Attack action on his turn to make an attack with a monk weapon or an unarmed strike, the monk can then use a bonus action to make an additional unarmed strike. Though this ability is less restrictive in terms of what weapons can be used, it is more restrictive in that the monk is also restricted in his ability to wear armor or wield a shield. In addition, martial arts attacks start with low damage (d4), but improve as the monk goes up in level, eventually reaching a d10 in base damage. Lastly, unlike with Two-Weapon Fighting that prevents the adding of damage to the bonus attack without the enabler of a Fighting Style, the monk can always add his Dexterity modifier to damage with this attack. On the whole, I grade Martial Arts as at least comparable if not equal to 'base' Two-Weapon Fighting for classes that don't have access to the Two-Weapon Fighting Style.

But that's not all the monk gets! At level 2, the monk gains Ki powers, one of which is Flurry of Blows. The only obvious restriction on Flurry of Blows is that the monk must spend a ki point and a bonus action to make the extra attacks. But the benefits are that the monk gets to make two bonus unarmed strikes, the monk isn't required to be unarmored or not wielding a shield, and the monk technically doesn't even have to attack; the rule for Flurry of Blows only specifies that the monk "take the Attack action on your turn", not that they use it to make an attack or to attack with specific types of weapons. Thus the monk could use a Flurry of Blows after making a shove or grapple attack (PBR, p.77, PH, p.195). And the restriction of spending a ki point grows less onerous as the monk goes up in level, as the monk has a number of daily ki points equal to his level, and recovers them all after a long or short rest; in the correct party (a fighter, monk, and celestial warlock walk into a dungeon...), a monk can often use many times his normal amount of 'daily' ki points between long rests.

So the real answer to 'how do Monks use the Two-Weapon Fighting rule' is, they don't -- they have better options in their class features, so there's no real reason for them to ever need to use the generic Two-Weapon Fighting rule.

How Rogues dual wield

The Rogue is an interesting case for Two-Weapon Fighting. On one hand, most rogues find Two-Weapon Fighting a bit too restrictive for their tastes; not only does it require the rogue to close to melee range (where the lightly armored character tends to be less viable than the more heavily-armored and higher hit-die front-liners like the Fighter, Paladin, and the like), but it also requires the rogue to use her bonus action to make the bonus attack, which the rogue generally wants to use for other things, most commonly a Disengage via Cunning Action. Most significantly, the main benefit that a rogue would gain from making multiple attacks in a turn doesn't actually apply, since the bonus damage from their Sneak Attack class feature can only be used once per turn; while making multiple attacks does give the rogue more opportunities to make a Sneak Attack, and thus less of a chance to pass through a turn without using her Sneak Attack, the trade-offs for a typical rogue generally aren't worth it except in exceptional circumstances.

However, with the release of the Sword Coast Adventurers Guide came the Swashbuckler Rogue, a rogue archetype explicitly designed to try to make use of Two-Weapon Fighting. This rogue doesn't gain any additional 'uses' of Sneak Attack, but she does gain an additional condition in which her Sneak Attack applies (via the Rakish Audacity feature), as well as the ability to move away from targets she hits in melee combat without requiring she use the Disengage action (via the Fancy Footwork feature); the former allows the Swashbuckler more flexibility in attempting to land a Sneak Attack and the latter allows the Swashbuckler a chance to get away from an opponent she's struck with Sneak Attack without suffering that opponent's melee wrath. The Swashbuckler was re-printed in Xanathar's Guide to Everything, so Organized Play games presume you are using that version of the class, but there doesn't seem to be any actual difference in the two versions printed in SCAG and XGtE, so from a practical standpoint, if you have either book, you have the ability to play a Swashbuckler, which would appear to be the 'official' way to play a rogue who wants to make use of Two-Weapon Fighting.

How casters dual wield

If non-Swashbuckler Rogues have a difficult time using the Two-Weapon Fighting rules effectively, then the casting classes, for the most part, have at least as difficult a time using that rule. Generally, the reasons for this boil down to one or more of the following:

Casters generally use spells rather than weapons to deal damage, which can't be used to enable a bonus attack via Two-Weapon Fighting.

In most cases where a caster does make a weapon attack, they do so via the Cast a Spell action rather than the Attack action, which also prevents the attack from enabling a bonus action attack via Two-Weapon Fighting.

Caster classes that do allow for actual weapon attacks often have restrictions within their class that make Two-Weapon Fighting difficult if not impossible to combine with their key class features.

Most caster classes simply don't have spells to buff their existing weapons; instead they typically create weapons that attack on their own using the character's actions or bonus actions

Reason One is pretty straightforward: most casters deal their consistent round-by-round damage via cantrips, whether that's the Warlock's Eldritch Blast, the Sorcerer/Wizard's Fire Bolt, or the Cleric's Sacred Flame. None of these are weapons, so they can't be used to enable additional weapon attacks via Two-Weapon Fighting.

However, the Sword Coast Adventurers Guide introduced a trio of 'weapon cantrips', cantrip spells that enable weapon attacks. These cantrips, Booming Blade, Green-Flame Blade, and Sword Burst, allow a Sorcerer, Wizard, or Warlock (mainly the Bladesinger Wizard also introduced in that book) to make weapon attacks by casting a spell. Note, though, that the Two-Weapon Fighting rule specifies that the character use the Attack action to make a qualifying attack, and these cantrips don't make use of the attack action; they each use the Cast a Spell action, and specify that the weapon attack made during the spell is "part of the action used to cast this spell". Since these spells don't make use of the Attack action, they also do not enable Two-Weapon Fighting.

But a Bladesinger Wizard might decide they want to try Two-Weapon Fighting anyway; though Bladesingers in prior editions tended to use longswords, nothing in the 5e version of the Bladesinger requires the use of that weapon; indeed, a sidebar of Bladesinger Styles in the SCAG points out that hafted weapons like axes or hammers have their own style, and both the light hammer and hand-axe are valid weapons for use with the Two-Weapon Fighting rule. At this point, though, you run into a potential issue with the key class benefit of the Bladesinger, the Bladesong, which ends if "you use two hands to make an attack with a weapon". Though some DMs do rule that this only prevents a bladesinger from making an attack with a two-handed weapon or a versatile weapon wielded in two hands, DMs familiar with prior editions of the Bladesong will often interpret this rule as preventing the Bladesinger from attacking with weapons in two hands.

To avoid this problem, you can switch gears and instead make use of the Hexblade Warlock, a warlock archetype that explicitly gains a bonded weapon that they can use with their class features. So long as this weapon qualifies for Two-Weapon Fighting, a Hexblade can use that rule with their bonded weapon. And it's at this point that you encounter the final problem with using Two-Weapon Fighting as a caster -- Rogues can use the rule to try to more reliably land their Sneak Attack, and Fighters and Rangers have class features that make the rule more efficient when used as intended, but casters just simply don't have spells that can be used to take advantage of having a bonus action attack available via Two-Weapon Fighting.

There are spells that buff a character's weapon, but most of these spells are Paladin spells, such as the various Smite spells (Branding Smite, Staggering Smite, etc.), and though they are cast on you rather than explicitly on one of your weapons, meaning they would trigger from a hit with a bonus action Two-Weapon Fighting attack, they only trigger once, meaning that you're not so much getting more use out of the spell as ensuring that the spell goes off more quickly. Of the few spells that buff weapons that aren't Paladin spells, the main one in the Player's Handbook/Player's Basic Rules is Magic Weapon, which Organized Play and games based on its rules of awarding magic items has rendered all but irrelevant (when every character has a magic weapon by level 5, there's little reason to learn or prepare a spell whose only purpose is to make a weapon magical after that point), and as with the Smite spells, most of the other spells buff you rather than your weapon, such as Tenser's Transformation from Xanathar's Guide to Everything, or Tasha's Otherworldly Guise from Tasha's Cauldron of Everything.

Lastly, there are spells that summon or conjure weapons, but most of these do so to create weapons that act on their own. The most familiar to most players is the Cleric spell Spiritual Weapon, which not only doesn't qualify for Two-Weapon Fighting, but is basically what the Cleric uses instead of Two-Weapon Fighting, as both the casting of the spell and the use of the spell to attack while the spell is running make use of the caster's bonus action, and since the conjured weapon is superior to just about any off-hand weapon a Cleric might wield at low level, it's hard to see a Cleric choosing to make use of Two-Weapon Fighting when they could nearly as effectively just cast Spiritual Weapon. The spells Mordenkainen's Sword and Black Blade of Disaster do similar things, but at much higher level, and again basically have effects that make anything you might want to do with an off-hand weapon attack pretty much irrelevant.

About the only spell that would in fact enable a caster to perform Two-Weapon Fighting is the spell Shadow Blade from Xanathar's Guide to Everything (page 164). This spell creates a magical sword that counts as a light weapon and that you use with the Attack action, which would trigger a possible bonus action attack via Two-Weapon Fighting if you as the caster are actually wielding a second weapon that qualifies (or conversely, might allow this weapon to serve as the bonus action attack after attacking with a different qualifying weapon in your 'main hand'). The downside is that the spell is a concentration spell, which means you can't conjure a second one while you already have one, and the blade is defined as disappearing if you drop or throw it, which likely prevents another caster from conjuring one and giving it to you. The damage of the blade also scales up as you cast it with a higher level spell, meaning that classes with limited spell level caps like the Arcane Trickster, who you might think would be ideal for such a spell, wouldn't get quite as much value from it as the classes that get it directly on their spell list, the sorcerer and warlock.

So, without actually doing the math, it would appear that the best Two-Weapon Fighter caster class would be the Hexblade Warlock with the bonded weapon in the main hand, and a conjured Shadow Blade in their off-hand, triggered by the attack with their main bonded weapon. This also means that the Hexblade could still cast Shadow Blade without the need to take the War Caster feat (noted below) in order to 'set up' Two-Weapon Fighting mode.

Final caveats and thoughts

There is one last rule that can impact the use of Two-Weapon Fighting, and that is the Dual Wielder feat (PH, p.165). That feat grants a slight bonus to AC when holding a weapon in each hand, allows you to wield weapons that aren't light and still use the Two-Weapon Fighting rule*, and most significantly, allows you to draw or stow two weapons in the same amount of time that you would normally use to draw or stow one weapon. This last benefit exposes perhaps the biggest unwritten restriction of Two-Weapon Fighting: the 'free' draw or stow a weapon action that characters get each round only allows you to draw or stow one weapon. So if you go into a combat with no weapons drawn, in the opening round you cannot make use of Two-Weapon Fighting without this feat, barring something like the Fighter's Action Surge or a friendly casting of Haste before your turn: either you draw just one weapon, leaving you without a second weapon to use to make the bonus action attack, or you spend your Action to draw your second weapon ("Use an Object", PH, p.192), leaving you without an Action to use to even attack.

* - This brings us back to the quote that leads this essay: the author points out that, even with the restriction of only using light weapons removed via the Dual Wielder feat, you still can't use Two-Weapon Fighting with a weapon that has the Two-Handed property, as the rule requires you to make an attack with a weapon in one hand, which you cannot do with a weapon with the Two-Handed property. The trick is that the author notes that 'a lot of' weapons with the Heavy property also have the Two-Handed property, suggesting that there are some Heavy weapons that you can actually use in Two-Weapon Fighting. This is incorrect, as every weapon with the Heavy property on the weapons list in the PH and PBR (the Glaive, Greataxe, Greatsword, Halberd, Maul, Pike, Heavy Crossbow, and Longbow) also has the Two-Handed property. There are weapons with the Two-Handed property that do not have the Heavy property (the Shortbow and Light Crossbow), but these are both ranged weapons and wouldn't qualify for Two-Weapon Fighting even if the Two-Handed property could be removed.

Normally, you can't hide from someone if you're in full view. A lightfoot halfling, though, can try to vanish behind a creature that is at least one size larger, and a wood elf can try to hide simply by being in heavy rain, mist, falling snow, foliage, or similar natural phenomena. It's as if nature itself cloaks a wood elf from prying eyes -- even eyes staring right at the elf! - Sage Advice Compendium, p.2

In Fifth Edition D&D, the rules for using Stealth to hide consist of three paragraphs in a sidebar in the section of the Player's Handbook that covers using Dexterity as an ability, so in a sense, it's a bit unreasonable for me to claim that DMs are doing Stealth wrong when the official rules support for how to actually do Stealth correctly is so sparse. Nevertheless, the actual rule does specifically state a distinction between hiding and being actually invisible ("An invisible creature can't be seen, so it can always try to hide. Signs of its passage might still be noticed, however, and it still has to stay quiet."), and as a result implies a distinction between being hidden and being invisible that, if stated explicitly, would make adjudicating Hiding situations correctly a lot easier...except for one thing.

The distinction is actually fairly easy to state, once you understand it:

When you are invisible, other creatures can't see you.

When you are hidden, other creatures don't know where you are.

Understanding the distinction between those two things makes a lot of what the rules do say make much more sense. For instance, the note above about invisible creatures being always able to hide; if you can't be seen, then you can attempt to move or otherwise mislead another creature into thinking you are standing in a place you actually aren't, or at the very least that it doesn't know that you're standing where you are. Whether you succeed or not depends on how you try to accomplish this, and whether you succeed at the appropriate check -- a Stealth check would certainly be appropriate if trying to move somewhere to make a creature think you're still in the space you 'disappeared' from, while not actually being in that space anymore, but misleading a creature, say by throwing a pebble to make a noise somewhere else, might actually require a Sleight of Hand check or even just a straight Dexterity check without a skill modifier.

But the most egregious use of Stealth is from those folks, often who have played a previous edition of D&D and gotten into the habit of using Stealth as a way of claiming a combat bonus -- this is true in 5E as well, particularly for the rogue class, as rogues not only can take advantage of the advantage granted by attacking an opponent who isn't able to see the rogue to gain Sneak Attack on that attack, but also by using the rogue's Cunning Action ability to hide as a bonus action either before or after attacking in order to set up the attack. And in this, the biggest aider and abettor of this kind of abusive rules exploitation is, sadly, the Sage, who seems to not really understand the distinction between being hidden and being invisible.

The Naturally Stealth ability of the lightfoot halfling does say that the character "can attempt to hide even when you are obscured only by a creature that is at least one size larger than you." However, nothing in the ability says that a halfling can do this while being observed, and the rules for hiding, scant as they are, do at least point out that "[y]ou can't hide from a creature that can see you". It's the next phrase, though, that really nails down the distinction we're trying to make here: "and if you make noise..., you give away your position." Being hidden is a matter of creatures not knowing where you are, and if you've given away your position (say by openly walking up to another member of your party and trying to hide behind them), any creature that saw you walk up to your fellow party member still pretty clearly knows where you are -- behind the other person.

Similarly, the Mark of the Wild ability of the wood elf does not provide an explicit exception to the general rule that you can't hide from creatures that can see you: "You can attempt to hide even when you are only lightly obscured by foliage, heavy rain, falling snow, mist, and other natural phenomena." Despite the Sage's flowery text, nothing in the ability actually allows the wood elf to simply vanish from the eyes of enemies simply because there's a heavy rain or snow falling.

So what good are these abilities if they can't be used the way the Sage implies? Well, there are two things to focus on in the rules, and then another thing to consider that's not explicitly within the rules, but probably should be.

The first thing to focus on that is within the rules is the use of the word 'obscured' in both abilities discussed above. Obscurement comes in two types, heavy and light, and heavy obscurement imposes the blinded condition on all creatures who don't have an ability that allows them to see otherwise (for example, mundane darkness is heavy obscurement, and thus blinds creatures that don't have darkvision; creatures that do have darkvision, though, can see even in the area). If a creature is blinded by being in a heavily obscured area, it can't see a creature trying to hide, which takes care of the problem that you can't hide from a creature that can see you. Light obscurement, though, generally only provides disadvantage to Perception checks, it doesn't prevent them entirely, so even though it may be more difficult to see in light obscurement, it's not impossible. Nevertheless, presuming that both abilities are referring to 'obscurement' caused by the things they describe in their text would allow characters with those abilities to attempt Stealth checks in circumstances where other characters could not; the effect of a successful check, though, is not to make the character invisible, but only to make the observer think that the character is still in the last space they saw them in -- recall, being hidden means that other creatures don't know where you are, but they won't just forget the last place they did see you, especially in a combat situation ("In combat, most creatures stay alert for signs of danger all around, so if you come out of hiding and approach a creature, it usually sees you."). If you actually are in the place that a creature thinks you're in, then you're not actually hidden, even if you made your Stealth check -- as noted above, you need to move to another position so you are not actually in the space the observers think you're in, or create some distraction or other misdirection to make those observers believe you're no longer in the place they last saw you. Being successfully hidden is what allows that misdirection to be successful, as being hidden means that while an observer may believe it knows where you are (based on where it last saw you), it actually doesn't. Admittedly, this may be a bit more difficult for a halfling hiding behind a single ally than for an elf hiding in an area of foliage consisting of multiple 5-foot squares, but neither is impossible.

The other thing to keep in mind is that the rules also explicitly say that "when you make an attack, you give away your location when the attack hits or misses." For people that want to do the 'attack, hide, repeat' mambo, this just means to them that they need to make a Stealth check each round, but keep in mind that once you've given away your position, not only are you no longer hiding, but creatures that you were hidden from, who didn't know where you were, now do know where you are. Trying to hide in exactly the same position you were just in creates the same problem as trying to hide in the space that creatures can actually see you're in before you try to hide; if your enemies think you're in the space you're actually in, because that's the space they last noticed you were in, you're not actually getting the benefit of being hidden. So what's the benefit of being hidden in combat if you're not invisible? That's easy, and spelled out right in the combat rules: "If the target isn't in the location you targeted, you automatically miss, but the DM typically just says that the attack missed, not whether you guessed the target's location correctly." If an enemy doesn't know where you are, and attacks a space it thinks you're in, but that you're actually not in, the attack automatically misses, and depending on the attack roll, the enemy might not even realize that he missed because you're not actually in that space.

There is one thing that isn't in the rules that probably should be, though, and it comes down to how enemies can detect you if you are hidden. Imagine you're a rogue and you sneak up to a wall behind which you can hear enemy monsters. There are archways to allow movement between the monster's room and where you are, but you're not standing in the archways -- you have full cover from the enemies and thus they can't see you. So you declare your intention to hide, which is perfectly reasonable: the creatures can't see you, and you want to be sure they don't know you're there. You make your Dexterity (Stealth) check against their passive Perception and succeed. Then, one creature leaves the group and walks through an arch into your area. You're hidden, so the creature doesn't know where you are, but you no longer have cover blocking the creature from being able to see you. Does the creature see you? (In previous editions of D&D, the creature would automatically notice you if it now had line of sight to you, which I always found irritating as a player.)

While there are many different situations that might affect a general rule (is the creature carrying a light source, or does it have darkvision? how much general detritus is there where you are that might provide additional cover or concealment from the enemy's location?), I'd argue that a general rule should be that, if you don't take an action that might reveal your position, enemies don't automatically get to spot you, though they could use an action to try to find you if they had reason to suspect you're there.

Going back to our imagined situation, when the enemy walks through the archway, as long as you're still not acting, you haven't done anything to give away your position, so the default hiding result -- the enemy doesn't know where you are -- continues. However, if the creature can see something that doesn't look 'normal' to it -- a gnome-shaped mass pressed up against the wall, for example -- it can attempt a Wisdom (Perception) check against your Dexterity (Stealth) check result to try to figure out that what it sees is you. If it fails, your ability to hide was good enough so that the creature presumes that it either isn't seeing what it thinks it sees, or that it misinteprets what it sees as something else (just a weird-shaped rock, for instance). However, if the creature then returns to the other room and you decide to move to the archway in the hopes of peeking around the corner and seeing just how many creatures are there, now you've done something that might give away your position; you need to attempt a new Dexterity (Stealth) check to confirm that your movement and action didn't give away your position, and if one of the creatures had actually come through the other archway stealthily without you noticing (it made a Stealth check against your passive Perception, so it's effectively hidden from you), then that creature would automatically notice you when taking your action, unless there was some other reason it wouldn't be able to perceive you while you are moving.

For many thinking creatures, alignment is a moral choice. Humans, dwarves, elves, and other humanoid races can choose whether to follow the paths of good or evil, law or chaos. According to myth, the good-aligned gods who created these races gave them free will to choose their moral paths, knowing that good without free will is slavery. The evil deities who created other races, though, made those races to serve them. Those races have strong inborn tendencies that match the nature of their gods. Most orcs share the violent, savage nature of the orc god, Gruumsh, and are thus inclined toward evil. Even if an orc chooses a good alignment, it struggles against its innate tendencies for its entire life. (Even half-orcs feel the lingering pull of the orc god's influence.) Alignment is an essential part of the nature of celestials and fiends. A devil does not choose to be lawful evil, and it doesn't tend toward lawful evil, but rather it is lawful evil in its essence. If it somehow ceased to be lawful evil, it would cease to be a devil. - Dungeons & Dragons 5th Edition Player's Handbook (first printing), p.122 When a character makes a choice, and that choice has to be graded as pushing them toward good or evil or whatever, who decides how that action is interpreted? That is to say, who is assigning good and evil, law and chaos? Who’s branding the characters? Some folks will say it is the character themselves, but that leads to a problem. Because most evil people don’t view themselves as evil. They either view themselves as working toward the greater good or they view good and evil as irrelevant. So, they are either good or neutral in their own minds. That means an outside authority is assigning alignments....

- Scott "The Angry GM" Rehm, "Angry Rants: Alignment"

I've been beating up the Angry GM in a few posts recently, so I figured I'd give the guy a break and talk about something he's absolutely right about.

This is not an article that discusses the history of the D&D alignment system, or hypothesizes that Gary Gygax slowly crafted the alignment system over time to impose a moral order on his game universe, mainly as a way to use Aristotelian thinking to fend off a rising tide of post-modernist relative ethics coming into popularity in the real-world.

This is also not an article that discusses what to do if you find that your players are trying to portray alignment as relative in a game system, such as AD&D or D&D Third Edition, where it is clearly deterministic, because of its inclusion in game mechanics. The Angry GM has already written that article, and his solution is about as good an answer as I've seen for that question.

This article is about alignment in D&D Fifth Edition, because based on the quote from the Player's Handbook that leads off this essay, the designers of D&D 5E certainly feel as though they can both eat their cake and have it on the alignment question -- player characters can have alignments that are not terribly binding on their personalities or in-game activities, while monsters are not nearly so flexible in their own moral and ethical outlooks. It's a game where you don't have to spend a lot of time debating whether or not to kill the orc babies, because it comes right out and tells you that the orc babies are going to be drawn to evil for their entire lives and do you really want to be responsible for making sure that decision never comes back to bite you in the butt? In short, the designers have tried to cut the Gordian knot of D&D alignment by providing what they feel is a 'best of both worlds' approach -- PCs can freely choose their alignment, and there is no mechanical function in the game that requires them to act according to that alignment (as an example, paladins, who used to lose their class abilities if they failed to act according to the Lawful Good alignment, now lose their class abilities -- and can optionally gain new ones -- by breaking the oaths they take upon reaching third level), but monsters still act consistently or even exclusively based on their own defined alignments, so that players understand how to interact with them.

This article also has two goals. First, to let the DMs and players (and maybe even the designers) know that there are a couple of odd wrinkles that come out of interpreting D&D alignment this way -- a minor one and major one in my view, but once you read them you can choose for yourself which, if either, is important to you. Second, to try to give you a way of handling alignment in your game that's different from the way you used to handle it in Third Edition, because that way isn't relevant anymore, and why that way isn't relevant.

So, berk, I guess we're all dead now

The minor oddness is that, in taking the position that the PC races listed in the Player's Handbook have flexible alignment choices (due to free will) but monster races don't and planar races definitely don't, they are basically saying that there will never be an official Fifth Edition version of the Planescape setting.

Planescape was a setting published by TSR in 1994 and became fairly popular and highly acclaimed, becoming even more acclaimed in the years since its release. Initially, the setting didn't seem to have much to do with the D&D alignment rules, as the key movers and shakers in the setting were a number of factions inspired by real-life philosophical movements, but the placement of the city of Sigil at the center of the Great Wheel of D&D cosmology slowly allowed alignment to creep into the setting -- by the end of the Faction Wars (or in other words, the point where TSR stopped publishing official material for the setting), many of the factions had fled to other Outer Planes, all of which were associated with specific alignment or alignment combinations that matched their philosophies.

This in itself isn't necessarily a bad thing or a game-breaker; Fifth Edition explicitly allows monsters to have innate alignments, like the modrons of Planescape do. The problem comes from the setting's tolerance for exotic player characters, especially characters who are partially or completely planar beings themselves. The tiefling, for instance, was first introduced in Planescape and proved so popular that it's been an option in every edition since, and a core option in both Fourth and Fifth Edition D&D. But based on the blurb from above, planar beings don't have optional alignment -- they are the embodiment of their alignment type, which would make them highly unlikely as player characters. (Of course, this doesn't seem to apply to Fifth Edition tieflings, though the designers work around that problem by defining tieflings as human with an infernal ancestor rather than a planar species born or created on another world.)

This becomes a problem in Planescape because the fans of the setting have basically embraced the idea that one of the 'cool' things about the setting is that creatures and characters could have alignments that were atypical for their type, exemplified in the video game Planescape: Torment that was released just prior to the year 2000. The main character in that game not only interacts with a number of creatures that don't match their planar alignments (a succubus that nevertheless loves the main character, for example), but also allows the main character to cycle through various alignments based on the player's in-game choices. For at least some fans, a loss of that sort of alignment freedom would mean the loss of what makes Planescape distinct from other D&D settings. A Planescape without the ability to play a lawful good succubus is a Planescape that won't satisfy some of the greatest fans of the setting, and thus won't be released.

I'm not racist, but...

The bigger oddity, in my mind, is that the definition of alignment used in D&D Fifth Edition is that it justifies racism. I referenced the 'orc babies' moral dilemma earlier, and it was a fairly common trope for DMs to use on their paladin and lawful good cleric players for a number of reasons:

it gave those characters some tough role-playing choices to make, potentially enhancing the role-playing experience

it often gave the DM a chance to let the players start building things in the world, such as an orphanage to house the orc children in so that they could learn to not be evil, or at the very least not to grow up with a grudge against the races that killed their parents

if the character chose 'incorrectly' (based on how the DM expected the dilemma should be resolved), the DM could 'punish' the players with loss of class abilities or even being kicked out of their class and/or faith

That last point tended to rub players the wrong way, especially if the DM had very specific ideas of how certain alignments 'should' be played and the players disagreed. In Fifth Edition, though, there's little reason to consider this a dilemma: if the orc babies are evil by nature, and will still likely turn out evil even if raised in a 'good' environment, there's little reason short of overwhelming faith to believe it's a better thing to spare them than to eliminate them and thus eliminate future evil in advance.

Even more to the point, when it's general knowledge that orcs are not just evil but innately evil, then there's no reason for anyone who isn't themselves evil to treat them with anything other than contempt and scorn, and seek to destroy them whenever they appear. This goes pretty well with a 'Lord of the Rings' style-setting (and D&D does owe a lot to Tolkien's creation), but it also means that, where there are orcs, there's a need for killing before they start it first. I'm not just inventing this as a hypothetical -- the Player's Handbook has explicit sidebars referencing the 'common folk' and their hatred of orcs and demons, which based on the way alignment works in Fifth Edition is entirely justified when discussing half-orcs and tieflings who aren't slaves to their alignments (but also don't walk around with big 'PC' signs glowing over their heads). This is especially jarring when contrasted with Fifth Edition's explicit tolerance for gender and sexual orientation among characters -- it's admirable that the shopkeeper won't give the transgender character a second look or a moment's difficulty over his/her appearance, but the orc won't be able to get the time of day, and according to the game's underlying structure, rightly so.

This becomes an even bigger issue when it is used to undo massive changes in campaign continuity. For instance, in the Forgotten Realms, author R.A. Salvatore presents a character named Obould Many-Arrows, who conquers land for the orc people to live on and, from that base, threatens many good settlements, including the dwarven fortress of Mithral Hall and the human city of Silverymoon. Yet by Fourth Edition, the orcs had settled into a more comfortable trading relationship with their neighbors, such that when forces align to try to spark war between the orcish state and their dwarven and human neighbors, heroes step in to side with the orcs and prevent it. In Fifth Edition, only a madman would assert that the orcs have any goal other than the domination of the surrounding races (which, oddly, echoes some real-world sentiments about terrorism, but that's far too big a subject to get into in detail now), because, well, they're orcs. I'm not sure the designers of D&D intended to use the alignment rules to effectively say, 'sexism bad, racism surprisingly OK', but there it is.

To use alignment, or not to use alignment

So how should you use this tool in your game? More importantly, how can you use the alignment rules in a way that doesn't contribute to real-world evils? You could probably just ignore the alignment rules, after all -- Fifth Edition has personality traits that are both more detailed than alignment when it comes to defining a character's beliefs and behavior (there are multiple different Ideals for each alignment type, for instance), as well as being actually tied to mechanical rules (playing to a character's personality is meant to trigger a reward of Inspiration, which can be used to gain Advantage on a d20 roll, a not insignificant benefit). Alignment rules are included in the Player's Handbook because old-school players wouldn't recognize the game as D&D without alignment, but the designers have all but removed the need for alignment in the game, so there's no real drawback to deciding that characters don't need to actually have an alignment, if that's the way you want to go.

On the other hand, if you do want to use alignment, then the best way to do so in my opinion is to take the recommendation of the Angry GM:

So, given all of that, given that the universe is going to assign people an alignment, what does it matter what a player chooses to write on their character sheet? Well, you can think of that as a statement of intentions. Not of the player. But of the character. When a player writes “good,” what they are saying is “my character tries to do the right thing.” When they write “chaotic,” they are saying my character puts individual freedoms first. But those are intentions. Those are what the character wants to believe. And if they write “evil,” they are saying they reject the idea of morality as a driving force to such a degree that they are willing to bring harm on others for their own selfishness. And when they write “neutral,” they are saying they just do what they do...But, here’s where it gets tricky. Every character SHOULD have a real, true alignment. One that reflects the universe’s judgment of them. And if you want to use alignment, you should keep track of that. And only reveal it through the world itself. For example, a “lawful-good” character who casts detect alignment might discover they are chaotic-neutral. Or they might learn they don’t count as good when they get struck with an anarchic weapon. Let them noodle that one over.

At the fourth tier (levels 17-20), characters achieve the pinnacle of their class features, becoming heroic (or villainous) archetypes in their own right. The fate of the world or even the fundamental order of the multiverse might hang in the balance during their adventures. - D&D Player's Basic Rules, p.10 For each character in the party, use the Adventuring Day XP table to estimate how much XP that character is expected to earn in a day. Add together the values for all party members to get a total for the party's adventuring day. This provides a rough estimate of the adjusted XP value for encounters the party can handle before the characters will need to take a long rest. -D&D DM's Basic Rules, p.57

In 'old school' Dungeons & Dragons, characters who advanced to high enough level would begin to take an interest in the campaign world beyond simple adventuring. Some characters might build fortresses or temples, others might start businesses. Eventually, your group might well stand up from a D&D session without having plundered one treasure horde or killed one orc, but rather spent the whole session trying to recruit novices from the downtrodden City of Harvendale or drive hard bargains with the trade guilds of Uventish to get a foothold in the lucrative markets there.

Don't get me wrong; I'm not knocking this style of play at all, particularly if everyone at the table wants to play that kind of game. Some of my favorite campaigns ultimately involved leaving the D&D rules behind and improvising our own world-building systems on the fly.

Starting in Third Edition, though, the designers figured out some games might head in that direction, and so provided some rules structure to support it. It provided detailed rules, for instance, on how long it took to craft a suit of masterwork plate mail, and how much longer it would take to make it magical +3 plate mail. The game incorporated the Leadership feat for those who wanted to recruit an army or found a city, and even devoted an entire splatbook to the process of building a stronghold.

Still, in Third and even Fourth Edition, the presumption was that characters who decided to devote time to these sorts of activities weren't adventuring -- that the 'clock' was running in the background slowly ticking off time that wasn't being spent plundering tombs. Sometimes, that wouldn't be so much of a concern -- I remember a long-running Forgotten Realms campaign set in the Sword Coast and the North where, when the winter months rolled around, adventurers typically went into hibernation, like bears, except instead of sleeping, that would be the time they'd spend crafting magic items and tending to their businesses, ready to return to the fields of battle come the spring thaw.

The designers of Fifth Edition D&D decided to abstract this process somewhat by introducing a new resource -- the 'downtime day'. By spending downtime days, you can do specific tasks in the game world, such as crafting, recovering from disease or poison, or practicing a profession. There are a few weirdnesses about the downtime system (for example, everyone in a D&D world who is proficient with the Performance skill is a rock-star, earning enough to support a Wealthy lifestyle when spending downtime on practicing that profession), but for the most part, it's a pretty solid abstraction for distinguishing between adventuring time and non-adventuring time.

However, there's one other bit of weirdness surrounding downtime -- it's not immediately clear where downtime days come from. The Player's Basic Rules simply presume that characters have downtime days they can spend on the activities listed, but they also seem to assume that downtime days are limited in some way. For example, one of the things you can do with downtime is learn a language or gain proficiency with a set of tools -- that takes 250 downtime days spent with a willing instructor. If there is no limit to the number of downtime days a character has access to, then any reasonably high-level character should have all of the tool and language proficiencies allowed in the game, since the expense is only 1 gold per day (plus lifestyle expenses), which any high-level should more than be able to cover from a typical 'tier 4' adventure.

You might, as a guideline, choose to award downtime the way it's awarded in the D&D Adventurers League -- each completed Expeditions adventure, or completed chapter in an Encounters or similar environment, results in an award of 10 downtime days. At first glance, this seems like a good guideline; you award enough downtime days so that characters have something to aim for, but not so many that they seem cheap and unvalued.

There's only one problem with this, though in honesty, it's more of a problem with adventuring time than with downtime, and it's a problem that really entered the game back in Third Edition.

Let's start with a simple statement of the problem, as it begins with a combination of the tables that accompany the two quotes at the top of this essay. To put it bluntly, D&D makes characters powerful far too quickly.

The table in the DM's Basic Rules lists the amount of XP that a single character should earn in a 'typical' adventuring day. While this doesn't preclude some days not reaching this 'typical' total, the simple use of 'typical' to describe that award suggests that it's more common than not to reach it, or even exceed it. So at 1st level, a character should gain 300 XP from a single day of adventuring. A 6th level character is expected to earn 4000 XP per adventuring day, etcetera, all the way up the ladder.

Now check the XP table in the Player's Basic Rules that tells you when you go up a level -- a 1st level character reaches 2nd level after earning 300 XP: in other words, after a single day's adventuring. (This particular combination is Fifth Editions solution to the 'low levels are boring' problem -- where Fourth Edition added more and more abilities to starting characters to make them more interesting and thus more powerful, Fifth Edition simply says, 'don't worry, you won't be stuck here long'.) The problem is that the advancement rate doesn't ramp up nearly as rapidly as you might expect it should: that 4000 XP per day that a 6th level character gains is nearly half of the 9000 XP she needs to go from 6th (14,000 XP) to 7th level (23,000 XP).

By tier, the advancement rate goes like this -- in tier 1 (levels 1-4), a character advances between one level per day (at levels 1 and 2) and one level per day-and-a-half (at levels 2 and 3). In tier 2 (levels 5-10), the advancement rate slows slightly, so that a character is expected to gain enough XP in two adventuring days to fall just short of making the next level, assuming she started at minimum XP for the current level. But then, starting with tier 3, the advancement rate speeds up again -- characters from levels 11 to 16 should earn enough XP per day to advance a level every day-and-a-half. And a level 19 character, starting at 305,000 XP, should reach the pinnacle of her power, level 20 (355,000 XP), in barely over a single day (40,000 XP per day).

A character goes from being basically a nobody -- an apprentice level character who hasn't even mastered all of her character abilities -- to one of the movers and shakers of the universe in just about seven weeks of adventuring. This is a huge contrast to AD&D, where reaching 'name level' might take years of in-game adventuring (and a couple of years or more of real-time), and each level after would take about the same amount of time as it took to reach that 'name level'.

Now granted, it'll likely take more than seven weeks of real-time gaming to get to maximum level, which is the real point of the system -- a game where you can only get to the highest levels by dutifully playing week after week for years is not a game a lot of people are going to play for that long. This does, however, throw a huge curve into the presumed system where the existing 'movers and shakers' are themselves only in their positions because they are high-level characters themselves. Did the king refuse your request to establish a church in his territory? Don't worry -- in another month you'll be higher level than he is and you can kick his ass then.

How do you reconcile a world where it only takes a couple of months to achieve world-shattering power, but most folks who have it are presumed to have spent years gathering that same power? Two options seem obvious:

Run your campaign like an anime, where anyone who is old and experienced will eventually be overthrown by a teenage prodigy, or

Throw enough downtime days at the party that years will actually pass while they advance to 20th level.

The D&D Adventurers League system is not going to give you enough downtime days to avoid this problem -- D&D Expeditions modules are set up so that the maximum possible XP a character can gain is roughly the same XP that the character would expect to earn in an adventuring day, so in effect you gain 10 downtime days for each actual adventuring day, or roughly 280 downtime days. That plus the adventuring days does manage to extend the world-shattering horizon from seven weeks to nearly a year, assuming your characters spend all their downtime days, but this doesn't really solve the problem. (More problematic is that this system doesn't actually let characters really use the downtime system as written -- such a character would be able to learn a single new language or tool proficiency, at roughly level 18, by hoarding her downtime.)

If you want a more 'realistic' system that supports the idea that existing powers in the world got there through hard work and leveling up, then what you want is a system by which a character advances from level 1 to level 20 in roughly 20-30 years of in-game campaign time, which implies a system where a character gains roughly a year or more of downtime each level, and is encouraged to spend that downtime freely in order to make the calendar run. (Well, that or you deliberately slow advancement so that, instead of getting to level 20 over the course of a couple of months, you get there over years, plus downtime.) So basically, whenever a character goes up a level, she gains 200 downtime days, plus an additional 75 downtime days for her level tier -- so going up to 5th level and reaching tier 2 grants 350 downtime days.

You might think you can prevent abuse via 'hoarding' downtime by declaring that any downtime days not spent when the next award is given are lost -- use 'em or lose 'em, as they say in Human Resources -- but sadly this doesn't work here, because forcing your players to lose downtime days goes right back into the 'we just started this gig two months ago and now we're here to save the world' problem you're trying to avoid by implementing this system. The cool thing is, you can assume your key NPCs did the same thing when they were adventurers, so the wizard-king likely has some impressive and unique spells he can bust out against the party, if they piss him off too much.

image from xkcd.com

The image above expresses one of two ways people generally treat rules in RPGs:

Anything that isn't expressly forbidden is allowed.

Anything that isn't expressly allowed is forbidden.

The first option is the default setting for so-called 'character optimizers', who take sometimes bizarre interpretations of rules and use them to break games. The second is often the refuge of players and DMs burned by these optimizers, in the hopes of preventing them (or at least delaying them) from breaking the current game.

There is, however, a third option, one that has been embraced by the designers of D&D Fifth Edition:

3. Anything that isn't expressly allowed or forbidden is the DM's call.

This approach codifies the DM's role as adjudicator, as well as being the authority on things in her campaign universe. The DM's ruling is always the final word, after which arguing is simply detracting from game time.

Given this, how do I justify claiming that people are, sometimes "doing it wrong"?

Well, simply put, while the DM is the final arbiter of how things work in her campaign, ideally she shouldn't be arbitrary about it -- if she specifically chooses for a given rule to work in a given way, that's absolutely fine, but if, on the other hand, she makes a ruling without really understanding how the associated rules are designed to work, it leads to a number of problems: players have a difficult time predicting what the results of their actions might be, which tends to limit players to only attempting actions where they know how the DM will rule, which limits the potential of gameplay, for one. Another problem is that an arbitrary DM can open up opportunities for rules abuse by not considering how rules work together; making the 'wrong' ruling makes it easier for unscrupulous players to break the game.

So, when I say "you're doing it wrong" to you as a DM, if you're fine with that and have a justification for why you're doing it wrong, that's actually cool. It's really only a problem if you don't know why you're doing it wrong and would rather do it right.

So let's start with a simple one: Actions in Fifth Edition. First, some history.

Prior to Third Edition, there wasn't really a concept of 'actions' or an 'action budget' in D&D. There was the idea that characters would get to attack once during a melee round (with some classes, mainly fighters and their sub-classes, getting more than one attack in some or all rounds), and with casting a spell basically substituting for making an attack. Outside of combat, you described what you wanted your character to do, and the DM decided how long it took for you to do those things.

Third Edition introduced an action budget -- a menu of things your character might be able to accomplish in the span of a single round. (For things that would take longer than a round, the action budget didn't really apply, and was handled within the game's skill system.) At the beginning, there were standard actions (like attacks), move actions (like, well, moving), and free actions (actions that didn't take any time in-game and could be done at any time, like shouting a warning). Some of the things Third Edition introduced, however, didn't really fit this structure (mainly the Quicken Spell feat), so sometime before the release of D&D 3.5, the budget was expanded to include swift actions and immediate actions -- the latter being swift actions you could do when it wasn't your turn, as long as you hadn't already used a swift action on your turn. It was kind of kluge-y and still involved things that didn't officially fit in the action budget (such as attacks of opportunity), but it was a solid start in making D&D a more tactical game for a new era.

Fourth Edition took the mess that was actions in Third Edition and codified it -- each player got a standard, move, and minor action on his turn, an immediate action that he could use when it wasn't his turn, and an opportunity action usable once on any single character or creature's turn. (The game still had free actions, but they became largely cosmetic, again mainly for things like shouting warnings.) Anything in the game that didn't require the use of an action was flagged as a 'No Action' activity. The game also used immediate actions to clean up the concept of 'triggered actions', mainly used in Third Edition for readying actions -- in Fourth Edition, a triggered action had a specific trigger, and it also specified whether the trigger was a reaction (which would occur after the triggering condition or action) or an interrupt (which would occur before the triggering condition or action). Attacks of opportunity were given their own specific action type -- the Opportunity Action -- which allowed the creation of abilities that could then replace an attack of opportunity with some other action. It still wasn't a perfect system, but the issues were much more corner-cases than they were in Third Edition. (Example: The Blinding Ward power allowed a character to blind a creature that attacked himself or an ally as an immediate interrupt, blinding the enemy before it made its attack. However, if used when the ally had provoked an opportunity attack, the attack should have been prevented, since opportunity attacks can only be used against targets that the attacker can see. But this prevents the triggering condition from going off, which means the power can't be used, and the attack happens, which triggers the power, etc. Most DM's resolved this paradox by allowing the attack with the -5 penalty for being unable to see the attacker.) The system was structured, but not any simpler, really, than the 3.5 action budget, and we've already discussed how later designers messed up the codification by allowing action types to 'bleed' into other action types, so by the time Fifth Edition rolled around, the designers knew they wanted to actually simplify the action budget, but not get rid of it entirely (the idea of an action budget is useful in encounter and monster design in that it helps the designer have a concrete idea of what a character or monster of a given power level should be able to 'do' in a round, and thus, for example, how many rounds a monster of a given amount of hit points should remain threatening).

So in Fifth Edition, the action budget actually was simplified. Characters got an Action, which they could use to attack, cast a spell, activate a magic item, or interact with a non-magical object. Characters could also use a single Bonus Action on their turn in addition to their regular Action, if they had an ability (often a spell) that could be used as a bonus action. Characters also got a Reaction, which, like a bonus action, could be used if something allowed them to spend their Reaction, such as making an attack of opportunity.

Aside: this is one area where DMs get actions wrong in 5th Edition -- they remember prior editions where the attack of opportunity was either its own action or its own action type, and don't realize that taking an attack of opportunity prevents a character from using another available reaction, such as a readied action. Another is that, in 5th Edition, unlike in prior editions, characters can take reactions on their own turn.

Another, unheralded way in which Fifth Edition simplified the action budget was by eliminating 'action exchange' -- in previous editions, actions had a hierarchy, and a character could trade an action that was higher on the hierarchy (such as a standard action) for an action that was lower (such as a move action). Fifth Edition simplified this by making the things you might want to 'trade' actions to do into actions of their own -- a character that has moved her full allowance but still wants to move farther can use her action to Dash. A character who wants to draw a weapon can do so as part of a single free 'interaction' action on his turn, but if he wants to put a weapon away and draw a different one, he uses his action to Use an Object for one of those interactions.

Notice something I didn't mention above? You guessed it -- 5E eliminated the 'move action'. Each character is now presumed to be able to move her speed on her turn, and can divide her movement however she wishes between her other actions, even using movement between parts of the same action. So a character with 30 feet of movement and the Extra Attacks feature can move 10 feet up to a monster, attack with the first attack of her Attack action, move another 15 feet up to another monster, attack with the second attack of her Attack action, and then move 5 feet away from that monster (possibly provoking attacks of opportunity if she didn't actually drop the monsters she attacked). This is something that both players and DMs who spent a lot of time working with the 3.5-era Spring Attack feat have a hard time wrapping their heads around, and is another thing those DMs and players tend to get wrong.

The big YDIW for this essay comes now, though: Can you take an action in the middle of resolving another action?

For higher level characters, this isn't really uncommon -- a character might be in the middle of resolving his Attack action when the monster's readied action triggers, allowing the currently acting character to attempt an Opportunity Attack. Can he take it? Or a different character makes the first attack of multiple attacks granted by Extra Attacks, drops the creature she's fighting, and decides she wants to cast a bonus action spell before moving to the next creature. Can she do this?

(Hint: don't bother looking in the Player's Handbook for this; the rules are silent on this question.)

My answer: Yes, they can.

Fifth Edition has already done away with a number of restrictions on when actions can be taken; reactions can be taken on a character's own turn, for instance, unlike in previous editions. Also, the rules explicitly allow movement to occur before, after, and during a character's action. Given these precedents, it's not a huge step to allow characters to take actions (usually a bonus action or reaction) in the midst of another action.

As I noted in the previous essay, the Angry GM has a pithy aphorism that applies to nearly any game-mastering situation, "You can run your game any wrong way you want." Based on the D&D Fifth Edition Adventurers League games I've played in over the past year, I can attest that a lot of you seem to be taking that advice to heart; there's a lot of stuff that people seem to be doing wrong when running D&D Fifth Edition.

My goal in the next few essays related to the 'YDIW' topic is to point out a number of areas where Fifth Edition DMs are having trouble adjudicating rules, and demonstrate both what the 'proper' ruling should be (at least from my own perspective), and why that ruling is 'proper'. For starters, though, we'll take a quick look at the most common reasons why DMs get rulings wrong in 5E.

Among experienced DMs, the biggest reason wrong rulings get made is that 5E uses the names of rules from previous editions, but changes how those rules work; as an example, just because 5E has an Opportunity Attack, doesn't mean that the 5E Opportunity Attack works the same way as the 4E or the 3E Opportunity Attack.

D&D 5E was designed with two main goals: first, attract new gamers to the game (i.e.: grow the market for D&D), and second, satisfy experienced D&D gamers that they're actually playing D&D. Fourth Edition was actually very successful in the first of those goals, but was perceived to have failed miserably in the second, due largely to the degree to which Third Edition D&D gamers migrated to Pathfinder instead of D&D Fourth Edition. But the first goal is arguably the more important goal -- next time you find yourself at a game convention, go poke your head into the room where the Warhammer games are taking place. You'll likely find that almost all the folks in that room are 50+ year old dudes, which both convinces younger dudes and pretty much all women that the game isn't for them, and adds the additional problem that, once those dudes start dying off, your game is pretty much done.

The sneaky part is that those two goals, at least with respect to D&D, aren't independent goals; if anything, the goal of growing the game is contingent on the goal of convincing gamers that 5E is 'really' D&D. Mike Mearls (one of the lead designers of 5E) has stated on multiple occasions that, since the number of people participating in geeky hobbies appears to be exploding in the past half-decade, there's little reason to think that D&D, as the godfather of geeky hobbies, shouldn't also explode. But there's a catch -- if you're trying to convince some friends that they should watch Doctor Who, you can tell them how awesome the show is, and all they need to do is find a way to watch some episodes to decide for themselves. You can pass around your own Doctor Who DVDs among the group, or let them figure out how to Netflix or otherwise watch on their own. They don't have to coordinate, and that's actually a strength -- because when one of them tries Doctor Who and comes back to the group to gush about how awesome it is, that alone will provide additional motivation for those still sitting on the fence to try Doctor Who.

But if you're trying to convince a group of friends how awesome D&D is, the only way to do that is to get them into a game, which means getting them to sit down at a table at the same time and play the game. Your local store may be sponsoring Adventurers League, but they're likely only doing that one night a week. So the most likely way to get them hooked is to coordinate everyone's schedule, get them all to sit down at your table, and run a game for them. And that's where the second goal comes in -- because if you're a gamer who's convinced that 5E isn't really D&D, you're not going to go to the trouble of doing that, or if you do, it won't be to run D&D 5E, it'll be to run Pathfinder, or Savage Worlds, or some other RPG that you are excited about. And if one friend does decide to try D&D separately, say by checking out a D&D Encounters night at the local game store, that person's experience becomes paramount to determining how likely others are to follow suit -- each episode of Doctor Who is fixed, and you can point your friends toward the better ones and avoid the less stellar episodes. A session of D&D is only as good as its DM, though, and if your local game store happens to be the fiefdom of a particularly crappy DM, then your attempt to get your friends to adopt your love of D&D may likely be toast unless you suit up and take on the role yourself.

So it's not just laziness that 5E D&D has Opportunity Attacks and fireballs and paladins; changing too many of the tropes of the game will lose you exactly those motivated folks you need to evangelize your game to the next generation of players. But a fireball in Fifth Edition doesn't work the same way that a fireball worked in Third Edition, so unless you're able to notice that and shift gears, you're going to confuse your new players, who don't have any idea how a fireball used to work and are only going to be puzzled as to why you're not allowing the wizard's fireball to work the way the book says it should work.

The other reason DMs get the rules wrong is a bit more subtle, and it boils down to the rules of D&D not explicitly covering how a specific situation should be resolved. This, again, is a feature of D&D 5E, not a bug, no matter how many optimization grognards want to argue otherwise. And again, you can blame D&D Fourth Edition for this.

In Fourth Edition, pretty much everything got a very precise definition, especially powers. A power could be used when it said it could be used, did what it said it did, and that was that. Some players, though, found this too restrictive -- if, say, a character was restrained by spider webs, the creative player wanted to be able to cast his Whirling Daggers spell on his ally to cut the spider webs and free the ally. If the DM was amenable, then that was OK, but many DMs simply chose to point out that the effects of Whirling Daggers don't specify that they end a restrained condition on a target, and so, to avoid potentially game-breaking precedents, stuck with the strict definition of what powers could do in combat.

Jeremy Crawford (the other main designer of 5E D&D) put it like this:

The DM is key. Many unexpected things can happen in a D&D campaign, and no set of rules could reasonably account for every contingency. If the rules tried to do so, the game would become unplayable. An alternative would be for the rules to severely limit what characters can do, which would be counter to the open-endedness of D&D. The direction we chose for the current edition was to lay a foundation of rules that a DM could build on, and we embraced the DM’s role as the bridge between the things the rules address and the things they don’t.

(That 'severely limit what characters can do' comment is a subtle elbow in the ribs of Fourth Edition D&D, as run by unimaginative DMs.)

So the rules for D&D Fifth Edition deliberately leave a number of things unanswered, with the understanding that the DM will answer those questions for her specific game, which is fine, if as a player you only ever play in one game. But some players, and I'm an example, play in many different games -- I've played in D&D Encounters at one game store, D&D Expeditions at another, and played Adventurers League at GenCon and plan to play more at other game conventions. Every time I go to a new venue, I get a new DM, which means all my assumptions about how certain parts of the game rules work effectively go out the window each time I sit down at a new table.

The key is that, while the rules don't directly address every contingency, they do set precedents and provide patterns that can be used to determine what the most reasonable interpretation of an unaddressed rule should be. That's why I can still say that a DM, who has the power to make any ruling she wishes at her own table, can still be 'doing it wrong' if she doesn't make the ruling that the rules seem to want her to make, even if they don't say so in so many words.