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I have been reading about this and am finding a lot of questions similar to what I'm asking, but they also all have extra components and I just want a simple answer. I think I already know but I am new to DnD so please bear with me.

I have a lvl 5 Assassin and I use two short swords. Assassinate ability says "In addition, any hit you score against a creature that is surprised is a critical hit."

Surprise condition is listed as "If you’re surprised, you can’t move or take an action on your first turn of the combat, and you can’t take a Reaction until that turn ends."

I asked my DM if that meant that if I surprise an enemy, would both my main hand and offhand crit, with only my main hand getting sneak attack?

His answer was basically, "to prevent overkill he is limiting the assassinate crit to only the attack action, and not the bonus action."

So my main attack would trigger assassinate crit, but not my bonus action attack. I don't agree but I can't find any official proof otherwise. I know in the end it's his call but that seems like it really limits me, because the whole idea of an assassin is to jump them right off the bat and then go to normal fighting. I feel the RAW backs me up but I don't want to push it.

How do I argue this? Should I argue this after he made a ruling? Am I even right? I love playing with them and don't want to push it, but I also want to take advantage of what seems like a major class feature.

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  • \$\begingroup\$ Welcome to RPG.SE! Take the tour if you haven't already, and check out the help center for more guidance. We can't really tell you "should I argue this", as that's an entirely opinion-based question. We can answer whether a ruling is accurate based on the rules, or what the best way to bring up a specific issue is, but what you "should" do is a question with no way to pick a single "best" answer; any such answer could be equally valid. \$\endgroup\$ – V2Blast Aug 4 '20 at 12:28
  • \$\begingroup\$ Rogue, duplicates aren't a bad thing (unless they're literally just copy/pasting another question). They provide different search terms that are likely to help other people find the "main" question. Please don't deface/remove your question, it's not an issue if it's been answered previously. \$\endgroup\$ – Purple Monkey Aug 5 '20 at 8:05
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You are right: By rules as written, both of your attacks will auto-crit

You already quote the relevant part of the rules yourself. The Assassinate feature includes:

In addition, any hit you score against a creature that is surprised is a critical hit.

Even if you hit your enemy with your first attack, they will still be surprised¹, as it is still the first round of combat. Hence, your second attack (and any further attack, if you have Extra Attack from multi-classing) on this turn can still make use of Assassinate and will therefore automatically be a critical hit, unless it misses.

¹: Note that, strictly speaking, being surprised is not a condition mechanically. See this question for more on that.

...but the DM is always right

D&D 5E explicitly empowers the DM to make rulings that need not always be in accordance with rules as written. If they think nerfing Assassinate like this is a good idea for their game, you'll have to discuss it with them. There are many questions on this site about approaching the DM about a ruling you do not agree with, a good one to start with could be How should I handle a ruling that really hurts my character?.

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