Can I Sneak Attack with a bonus action, then Ready another Sneak Attack?

Question

I have a twf rogue with throwing daggers. I use my bonus action to sneak attack an enemy.

• Can I Ready action after I use a bonus action?
• Does Readying action count as a separate turn?
• Can I attack with a throwing dagger as a bonus action to proc SA, Ready action (for a later turn), throw another dagger to proc SA during the same round?

Answer 1

In order:

You can take the Ready action after you use a bonus action, sure. What really matters though is how you get your bonus action. If you just have a feature that lets you take your bonus action without any conditions then you can go ahead and do that. But some bonus actions have conditions that must be met in order for you to take them, like the one from wielding two weapons, as I will detail below.

Taking the Ready action does not count as a separate turn. What happens is, you decide on a triggering event, something you can perceive that you will react to in the future before your next turn. Then you pick the way you want to react to it. For example, you can take the Ready action to respond to an enemy approaching your companion and respond by throwing your dagger at him. Note: In order to actually respond to the trigger you described, you must use your reaction for the turn.

Two Weapon Fighting(PHB Page 195):

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.

(Relevant Portion)

So from here we can see that, in order to get your off-hand attack with your bonus action, you have to have already taken the Attack action. This eats up your action for the turn, so you will not be able to take the Ready action like this, unfortunately.

What this ultimately means is that you wouldn't have a way to throw a dagger as a bonus action (unless you found a way in-game, like if your DM gave you a magic item). If you could do it though, you would be able to make both attacks with Sneak Attack, as RogueBurger points out in his answer with a reference to a Jeremy Crawford tweet.

Answer 2

According to Crawford:

Yes. The Sneak Attack restriction is once per turn, not once per round.

So as long as your reaction happens on someone else's turn, you can apply sneak attack to it.

Answer 3

Yes, to your first question; and if your Readied action triggers on a different turn, then you get to add sneak attack damage (see related question). To answer your third question, yes IF you have a feature that enables you to attack with your thrown dagger using a bonus action.