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I am playing a crossbow expert ranged rogue and trying to maximize my sneak attack capabilities in order to remain competitive with regard to DPR (Paladin and Fighter in the group).

I am wondering if by RAW, I can use the bonus action attack provided by this feat first and then if it is successful, ready my regular attack to trigger on someone else's turn - essentially allowing me a chance at two sneak attacks within the round.

I am solo-classed, so I don't have access to Extra attack and not looking to abuse Haste. I am wondering if this is in DM-rule territory or if there is some source I can point to that would allow something like this?

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    \$\begingroup\$ Welcome to RPG.SE! Take the tour if you haven't already and see the help center or ask us here in the comments (use @ to ping someone) if you need more guidance. Good Luck and Happy Gaming! \$\endgroup\$ – Someone_Evil Sep 12 '20 at 18:38
  • \$\begingroup\$ Related: Bonus action before Action for Crossbow Expert? \$\endgroup\$ – V2Blast Sep 13 '20 at 8:32
  • \$\begingroup\$ Note that Extra Attack wouldn't help you attack once on your turn and once on someone else's turn. You either use your action to ready one attack (and get no attacks during your turn because you haven't taken the Attack action), or you make up-to 2 attacks as part of the Attack action during your turn. (And could then make a 3rd as a bonus action with Crossbox Expert or dual wielding.) This cheese basically requires Haste or Action Surge to get another whole Action, not an extra attack as part of one action. \$\endgroup\$ – Peter Cordes Sep 13 '20 at 13:07
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If you are readying an action you aren't taking the Attack action

In order to take the bonus action attack of Crossbow Expert you have to take the Attack action (emphasis added):

When you use the Attack action and attack with a one-handed weapon, you can use a bonus action to attack with a hand crossbow you are holding.

Player's Handbook, p. 165

The Attack action (PHB 192) let's you take an attack on your turn, while the action which lets you take an action on another turn (as a reaction) is the Ready action (PHB 193). If you are taking the Ready action you aren't taking the Attack action on your turn (which is when you can take bonus actions) and thus can't take the Crossbow Experts bonus action.

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    \$\begingroup\$ @Someone_Evil Yeah, that covers it. Although in the extremely rare but theoretically possible case that you ready an attack and then the trigger occurs on your turn, you probably would then be able to take the bonus attack as well. \$\endgroup\$ – Ryan C. Thompson Sep 12 '20 at 20:03
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    \$\begingroup\$ @RyanC.Thompson That sounds like a different Q&A (if we haven't got it already) which is not relevant to the querent, and that would not help their rogue get more sneak attacks. \$\endgroup\$ – Someone_Evil Sep 12 '20 at 20:23
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Only if you have two Actions available and use one to take the Attack action.

In order to benefit from the Crossbow Expert feat, you need to be taking the Attack Action, but in order for you to ready an action, you need to take the Ready Action. As a result, if you want to do both, you're going to need to have two Actions available to use on your turn.

The two most notable examples of this would be if you're either a Fighter using the Action Surge ability or you're under the effects of the haste spell.

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