Rogue Squadron

My first long-term D&D character way back in the days of B/X, was a thief. I loved the character's special talents and potential to land deadly sneak attacks. I also liked that the class was a challenge to play. Poor AC and low hit points meant that you had to be quite careful in how you approached the game.

Over the years the thief evolved into the rogue, and its unique skills became a core part of the game. Backstab was watered down into sneak attack, which was powerful but an expected part of the rogue's abilities. Failing to gain sneak attack damage was a fail state, as opposed to backstab's massive damage spikes.

I think the rogue and ranger have ended up in a similar spot. Both had unique abilities that eventually became available to every character. Both struggled to find niches, though the rogue's cunning action feature in 5e helped it stand out.

For this revision, I've tried to focus on aspects that make the rogue stand out as a clever character who is one step ahead of their enemies.

Superior Proficiency

The rogue has a higher proficiency bonus than other classes. In my mind, this is a simple, easy way to capture the rogue's skill supremacy. It also feeds into saving throws, making them the best at dodging spells, resisting magic, and so on. I like that benefit for the class called upon to sneak ahead of the group in a dungeon.

Cunning Strike

I've given the rogue two basic options in combat, extra damage or the option to effectively hide from a creature even if conditions prevent stealth. The idea is to let the rogue press the attack or dash away to safety depending on how the fight is going.

Tools of the Trade

I like the idea of the rogue turning mundane or weak weapons into deadly tools, reflecting the class's expertise and mastery. Tools of the trade enables a rogue to function as a knife fighter, club wielder, and so on, and makes overlooked weapons like the sling useful options. I am 100% channeling the Fritz Leiber stories here by punching up a selection of weapons often wielded by thieves in those stories.

Cunning Action and Sneak Attack

These survive in spirit from the 5e SRD, with some adjustments made to account for the simpler, boiled-down take on 5e I am creating. I wanted to make sure that the rogue excelled at handling traps and locks, while upping the class's mobility and stealth with options that other classes simply can't access.

Artful Dodger

I'm not a big fan of uncanny dodge. It's so useful that it cuts off other reactions for the rogue, but in play it feels very static. The cunning, agile rogue stands there and halves damage without doing anything. I also wanted something that felt useful in exploration our outside of combat.

A free hide or move felt like a nice, versatile piece. A rogue sneaking around can attempt to hide from a guard or monster they blunder into, or turn tail and run before facing any attacks. A rogue who is already hidden gets the best of both worlds. They can move past a guard or slip into a better position when they encounter another creature. While it lacks the pure mathematical impact of half damage, artful dodger strikes me as fun and evocative.

Favored Fortune

I'm a little fixated on non-traditional cool downs, and felt that a luck ability that had a random chance of sticking around felt like fun. I also think that if any class could have a claim to luck, it would be the rogue. I also wanted to capture the feel of a skill expert who could outwit the vagaries of the d20.

Steady Eye and Deadly Edge

Frankly, the rogue in the SRD has some pretty lame features. The class is heavily dependent on sneak attack to deal damage, and its higher levels are littered with narrow benefits that I don't think carry their weight. I wanted to give the rogue a counter to their single attack, so half damage on a miss felt like a good benefit. Boosted critical feels much more fun on the class throwing fistfuls of d6s rather than the champion fighter. When the rogue crits, the monster really, really feels it.