[RPG] use Booming Blade and Sneak Attack, and then use Disengage (if the first attack hit) or Two-Weapon Fighting (if it missed) on the same turn

advantage-and-disadvantagednd-5emulti-classingroguetwo-weapon-fighting

I am building a rogue-warlock multiclass in D&D 5e. I get advantage using my familiar's Help action. And because it is near me, I can use Sneak Attack as well.

I am thinking about using booming blade. I know you can't make your second attack with booming blade.

So can I make my 1st attack with advantage, then use booming blade, then use Sneak Attack, and after that use Cunning Action to Disengage?
And if my first attack misses, can I make a second attack with my other shortsword and after that use Sneak Attack (I won't use Disengage or booming blade with my second attack)?

Best Answer

Booming blade is a spell and thus does not use the Attack action

The core misunderstanding here, as far as I can tell, is that booming blade is a spell and thus uses the Cast a Spell action and not the Attack action. And you choose which action to take before making the attack. I'll try to run down what works and what doesn't.

To get them out of the way, booming blade and Sneak Attack does work, your familiar can grant andvantage and qualify you for Sneak Attack, and because Cunning action has no restrictions you could use your bonus action to Disengage. Cunning action has no relation to attacks, other than using the same action economy as they (generally) use (as it uses your bonus action).

However, even if the attack misses, you have still taken the Cast a Spell action, and not the Attack action required for Two Weapon Fighting (which is the rule which would let you take an attack with your other weapon as a bonus action). Note that you can only take one bonus action per turn (PHB p. 189), so you could never use two weapon fighting and cunning action of the same turn.