I've been playing 5th Edition Dungeons and Dragons since its initial release. I've been consuming media about it. I've been buying supplements. And, sorry to say, I am a rules lawyer.
Hence, I have compiled this list of nine commonly misunderstood rules in 5th Edition D&D.
1. Every time you pick up a d20 you are making an ability check.
This is the basic mechanic for the 5e ruleset. Roll a d20, add an ability bonus, and add your proficiency bonus, if that is relevant to the check.
For a melee attack roll, you roll a Strength check. For a ranged attack roll, you roll a Dexterity check. For a spell attack roll, you roll an Intelligence, Wisdom, or Charisma check, depending on the particular spellcasting class you are. Attack rolls add your Proficiency bonus, as long as you are proficient with the weapon you are using.
A saving throw is the relevant ability check, with your proficiency bonus if your class has proficiency in that saving throw. Each class grants proficiency in two abilities. One of these will be one of the three most common saving throws - Dexterity, Constitution, or Wisdom. The other will be Strength, Intelligence, or Charisma.
Skill checks are the interesting one. A skill check is just an ability check, and you can add your proficiency bonus if it seems appropriate. Skills are listed with abilities, but that doesn't mean they always have to be that. If you want to roll a Performance check with Intelligence instead of Charisma, and you can make a reasonable case to the DM why it should be so, you can do that.
2. There is no flanking rule.
You do not get advantage on your attack roll for flanking your opponent. The reason for this is that flanking is a special ability that kobolds and wolves have called Pack Tactics, and a special ability of the Rogue class. Kobolds, goblins and rogues can get advantage if an ally is within 5 feet of their target (rogues can also get Sneak Attack damage if this is the case) but you don't have to be physically flanking your opponent like in earlier editions.
Giving the ability to everyone negates this special advantage.
3. You can't hold your initiative.
At the beginning of a combat encounter, all creatures roll intiative. This randomises the combat order, giving priority to people with high initiative scores. If the rules allowed you to "hold" your turn so that you go at a different place in the order, then what was the point of rolling in the first place? Why doesn't everyone just hold their turn and act when they want to?
Instead, on your turn you can take the Ready action. You specify to your DM what you want to do - an action - and when you want to do it - the triggering event. When the triggering event occurs, you can use your Reaction to act out of turn.
Note that you get only one Reaction per turn. If you do this, you can't take an Attack of Opportunity or cast a Reaction spell like Feather Fall or Shield. Or if you do, you lose your prepared action. If you're patiently waiting for the goblin to pop his head out of cover but then the ogre shoves you off the cliff, it's probably worth losing the prepared shot.
4. There is no critical fail
You don't automatically succeed on a natural 20, and you don't automatically fail on a natural 1. Attack rolls do a critical hit on a natural 20, but there is no additional penalty for rolling a 1. Some groups house rule critical failures, but there is a problem with this. It is generally quite easy to avoid rolling a natural 1. Halflings almost never suffer critical failures, for example, due to their Lucky trait. Several feats allow you to re-roll 1s. You have to be especially unlucky to roll a 1 that you cannot just avoid in some manner.
5. There is no move action in your turn
In your turn, you can do three things: move up to your speed, take an action, and take a bonus action if you have one. Your move can be split up as much as you want before or after your action and bonus action. Moving does not take an action. You can take an action to Dash, which allows you to move your speed, effectively doubling the distance you can move.
6. Twinned Spell
Boy, the Sage Advice column is full of this. If a spell is capable of affecting more than one target, it can't be Twinned. That's it.
7. You still need to carry a lantern
A lot of the races in D&D get Darkvision. Some parties arrange to have all Darkvision-enabled characters in their party so they don't need to carry torches and lanterns.
Darkvision does not mean that you can see perfectly in the dark. It means that you can see in complete darkness as though it were dim light, and you can see in dim light as though it were bright light.
Dim light is not good. Your range and visual acuity suffer, and you cannot make out colours. I would not blame a DM for setting a puzzle for the characters that depends on colour vision for its solutions, just to push home the message that Dwarves and Elves still need a light source.
8. You cannot go below 0 hit points.
Zero is the floor. There are no negative hit points. When you hit zero you are unconscious and you start making Death Saves. There is no need to track how far below zero you go.
9. Grappling
This is actually very simple. If you want to grab someone, you make an Athletics check, opposed by their Athletics or Acrobatics check. If you beat theirs, then they have the Grappled condition.
The effect of the Grappled condition is that they can't move. That's it. It doesn't stop them from taking actions. So yes, you can cast Shocking Grasp while you're grappled. Alternatively, you can make a Strength or Agility check to try and escape the grapple. Electrocuting someone who's got you in a bear hug may be satisfying, but unless you take them to 0 hit points, it won't get you out of the bear hug.
So there it is. Nine commonly misunderstood rules in Dungeons and Dragons. If you have any questions, read the rulebooks. You'd be surprised how many rules questions can be answered with the simple formula RTFM.
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