
Sandslice |

So... a debate came up just recently.
The Haunted Heroes version of the Pact Wizard has an ability called Great Power, Greater Expense, with the following effects:
- At level 5, you gain an Oracle Curse as though you were an oracle of half your PW level. Any spells gained from this Curse are counted as wizard spells and added to your spellbook.
- At level 10, you gain a resource (3 + level/2 per day) which allows you to get advantage on a save, CL check, concentrate check, or initiative, declared as a free (out of turn OK) action at the time of the roll. At level 15, you also gain insight +Int to these advantaged rolls, and can reduce the cost of metamagic by 1 level total on your patron and Curse spells.
It's at level 20 that the debate happens.
At 20th level, whenever the pact wizard invokes his patron’s power to roll twice on a check and his result is a natural 20, he automatically succeeds, regardless of whether or not a check of that type would normally allow an automatic success.
What does it mean to "automatically succeed" on initiative checks?
For example, suppose Billy has a +20 bonus on his initiative, and rolls a nat 20, reaching 40. Pact Wizard Jimmy has a +16 even considering his insight bonus, and gets a nat 20, reaching 36 plus "automatic success."
Who goes first, and why?

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"Advantage"?
At 10th level, the pact wizard can invoke his patron’s power to roll twice and take the better result when attempting any caster level check, concentration check, initiative check, or saving throw. He can activate this ability as a free action before attempting the check, even if it isn’t his turn. He can use this ability a number of times per day equal to 3 + 1/2 his Intelligence modifier.
Your citation is a bit off.
Regardless, an automatic success does something only if a die roll could fail on a natural 20, like skills. In initiative, an automatic success does nothing, because initiative hasn't a success/failure result.

Sandslice |

Sorry - I'm prone to using "advantage" as shorthand for "roll twice keep better" nowadays >.<
That said, that's what I thought - but the other fellow was arguing that somehow you "succeeded" at initiative by having the highest roll. It felt like a strange argument when the initiative check doesn't call out success or failure in its definition, hence the question.
Thank you!

Derklord |

but the other fellow was arguing that somehow you "succeeded" at initiative by having the highest roll.
Ask for a rule quote that says this.
Because that's how the rules work. The Initiative rules don't use the word "success" (unlike all the rules for the other respective rolls), and therefore, there is no definition of success for Initiative. "Success" needs to answer a yes/no question, and "in which order do the combatants act" is not such a question.

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Sandslice wrote:but the other fellow was arguing that somehow you "succeeded" at initiative by having the highest roll.Ask for a rule quote that says this.
Because that's how the rules work. The Initiative rules don't use the word "success" (unlike all the rules for the other respective rolls), and therefore, there is no definition of success for Initiative. "Success" needs to answer a yes/no question, and "in which order do the combatants act" is not such a question.
I would apply the "success" effect in a niche case when speaking of initiative: it you tie. In that instance, you automatically win the tie-breaking roll.
But that happens (in my experience) maybe two times in a campaign.