[RPG] What are the mechanics of an Arcane Trickster using an Owl familiar’s Flyby ability to gain Sneak Attack


I'm coming from a 5e campaign where there were house rules for a lot of things, including familiars, and I'm trying to understand exactly how an Arcane Trickster would use an Owl familiar's Flyby ability for Sneak Attack. I know that if the familiar is within 5 feet of an enemy I as a rogue can use Sneak Attack if I hit that enemy, and I know that the flyby ability means an owl familiar doesn't provoke opportunity attacks.

What I can't figure out is exactly how all the pieces fit together given that the familiar acts on its own initiative. Like, if the familiar has a lower initiative roll than I do, does the familiar hold its action until my turn, and then do a flyby of my opponent, and then I attack? Or does the familiar do a flyby when its turn comes and then I just keep that in mind when I attack? Or am I misunderstanding flyby and it's actually movement rather than action?

Let's say I'm in solo combat with two enemies and the initiative order is Enemy 1—>Owl familiar—>Enemy 2—Me.

Can I both get sneak attack by having the owl within 5 feet of my target and have the owl avoid attacks of opportunity? If so, how and when do I do it?

Best Answer

Use your action to Ready an attack for the Owl's flyby, and have the owl use Help.

This method allows you to do exactly what you're trying to do. On your turn, you use the Ready action to make your attack, with trigger "my owl is within five feet of my target". Then on your owl's turn, the owl flies to the target, triggering your readied attack with Sneak Attack, then flies away.

This tactic can be made even better by having the owl use the Help action when it reaches the target, giving you advantage on your attack.

You're a rogue. You won't feel like you're missing out on Extra Attack when you use Ready, because unlike fighters, your secret sauce works even when it isn't your turn.

If your Owl is immediately before you in the order, you can make the attack on your turn.

This method only works if your target does not take its turn between your owl's turn and your own.

  • Owl flies to within five feet of target.
  • Owl uses Ready action to fly away from the target after you attack.
  • Your turn, you attack with Sneak Attack.
  • Owl uses reaction to fly away.

If the target has a turn between the Owl's turn and your own, the owl is vulnerable to melee attacks from the target while waiting for your turn.

Talk to your DM about commands and narrative.

There is one final consideration here, and I have played this both ways. You need to discuss with the DM about how to handle the commands given the familiar. For example, at one table, the DM let me just control the familiar as I would my own character. However, at another table, the DM required that anything the familiar did on its turn had to be the result of a telepathic command issued in-character on my own turn. If your DM requires in-character commands, these situations might get a little weird or difficult to reproduce.

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