Scout

Exploring - While exploring a rogue usually scouts ahead of the party. This primarily involves stealth and perception. While moving stealthily they have to keep a sharp eye out for foes, traps and hidden doors, and take careful note of all the details they see in order to relay them to the party so that the party can make good decisions on how to proceed. Rogues can disarm the traps they see (making the path safe for the party) or navigate past them leaving them armed (so noone notices the intrusion), or even reposition them (so that they can be used against the people that set them). At each door they see they should press their ear against it and listen to discern if there are any enemies on the other side. Then they may need to pick the lock before quietly opening the door slightly and poking their head in to see what is there. Getting past guards or accessing rooms through windows may involve climbing walls or making long jumps between buildings. Rogues may also have to squeeze through narrow openings and swim moats and waterways to fully scout out an area to try to find the safest routes through for the party. Moving stealthily requires Dexterity (Stealth), perceiving requires Wisdom (Perception), and climbing, jumping and swimming requires Strength (Athletics).

Thief

Stealing – Sneaking into a room and stealing the item the party is seeking may make a quest much shorter and be safer than having everyone fight their way in and out. Making off with an inattentive enemy’s weapon or magic item before the party engages them will make for an easier fight. Rogues using Dexterity (Sleight of hand) can pick the pocket of a noble perhaps to gain a letter which gives the party an important clue or a key for easy access to a house or castle.

While sneaking around exploring, a rogue can pocket any expensive jewellery or magic item they see, even if it has been carelessly left lying around in a locked chest, ensuring they get the best pick of the treasure.

Assassin

Killing – Sneaking up behind the lone guard and making a sneak attack might instantly kill them giving the party quiet entry to a building. In combat, a rogue can take advantage of gaps in a person’s defence to make more deadly attacks as long as they have advantage on the attack or if the person is distracted by another combatant next to them. These sneak attacks allow them to do more damage using a small knife than the strongest fighter can with a great axe.

Note that sneak attack can be used very effectively with ranged weapons as shooting from hiding gives advantage on the attack, so as long as the rogue is not at long range (which would cancel out the advantage) they can sneak attack.

Rogues can use their cunning action to disengage or hide after every attack they make in order to make it safer for them. In melee combat they can attack an enemy someone else in their party is already attacking, then disengage to move half their movement out of the enemy’s range, then move back in on their turn to attack again. In the case of a ranged weapon, they can hide after every attack which means they cannot be the target of return fire.

One final point is that if a rogue uses their cunning action to dash they can surprise people with how far they can move around the battlefield. In the same round they can dash twice, moving three times their speed in a round. If they hide as their action and then dash while hidden they can pop up next round in a very different location.

Con artist

deception – Using persuasion, deception or intimidation to manipulate people in order to get their way. These skills use Charisma.