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Suppose I'm playing in combat as a 2nd level fighter/3rd level rogue assassin, and at least one more party member surprises the enemy. We have higher initiative.

Can the assassin use his action to score the autocritical + sneak attack, and then use the fighter's action surge feature to use a ready action to repeat attack against the same target, triggered on some action taken by his other party member?

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    \$\begingroup\$ Hi Piero. Your question is extremely rambly and difficult to parse. Since you're asking if you can do something specific with a specific build and have it work out a specific way, could I suggest you edit this to just describe (clearly): the relevant parts of the build, the actions you're trying to take, and how you think it will work out, and strip out the rest? E.g. I'm pretty sure I can just delete the whole first paragraph, and strip the second down to "I'm making a fighter 2 / rogue 3, who will have action surge, the assassin archetype, and the alert feat and stealth expertise." \$\endgroup\$ – doppelgreener May 15 '17 at 9:48
  • \$\begingroup\$ you are right i tend to do that, i will edit \$\endgroup\$ – Piero May 15 '17 at 14:53
  • \$\begingroup\$ One thing that might help with these scenarios is the writing practice of voyage out, voyage in. You voyaged out already -- this would be the voyage in. \$\endgroup\$ – doppelgreener May 15 '17 at 14:55
  • \$\begingroup\$ Thanks for taking that request on board. That's quite a good editing effort! :) \$\endgroup\$ – doppelgreener May 15 '17 at 15:16
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Yes, this is legal

As long as you hit with both attacks -- the one on your turn and the one on your ally's -- you can autocrit with Sneak Attack damage on both. All the requirements of Sneak Attack and Assassinate are fulfilled.

Other builds that can do this

These MC builds achieve the same thing at a later level, but here's to illustrate that you can do this without Action Surge, using just your regular Action.

  • A Sorcerer 3/Rogue Assassin 3 with Quickened Spell

    • Quicken Green Flame Blade or Booming Blade (GFB/BB) for a bonus action, and then use their action to Ready another GFB/BB
  • A Wizard 5/Rogue 3, or Sorc 5/Rogue 3, or Lore Bard 6/Rogue 3

    • Pre-cast haste to receive an extra action before the surprise round begins. During the surprise round, use that extra action to make a regular Attack, and use your regular action to Ready a second regular attack (you may not ready a spell as Readying a spell requires Concentration, which haste already takes up)
  • A Frenzy Barb 3/Rogue 3, Strength-based

    • Use Frenzied Rage as a bonus before the ambush, and during the surprise round, use their bonus action to make one weapon attack. They can use their action to Ready another attack.
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