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I am unsure of how the Circlet of Persuasion is supposed to work, specifically what checks it applies to.

It says:

This delicately engraved silver headband grants its wearer a +3 competence bonus on Charisma-based checks.

Does this apply to Charisma based skill checks or just Charisma ability checks, just like breaking something is a Strength check?

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Rolls basically come in three flavors: “rolls” (e.g. attack, damage), “checks” (e.g. ability score checks, skill checks), and “throws” (i.e. saving throws). A circlet of persuasion only applies to the “checks,” and not to “rolls” or “throws.” And it certainly does not apply to anything based on Charisma that doesn’t involve rolling a die, like for example a sorcerer’s bonus spells or save DCs. Basically, you need to see the word “check” somewhere if you want it to apply.

But it does apply to all checks involving Charisma, rather than only ability score checks. The wording for that would be a “bonus to Charisma checks” rather than a “bonus to Charisma-based checks.” So yes, it does apply to skills and some other things.

Major examples:

  • Ability score checks, e.g. the Charisma check made during planar binding

  • Skill checks, e.g. Perform or Use Magic Device

  • Concentration checks, e.g. for a sorcerer

Major examples that are not checks:

  • Non-dice-based things, like bonus spells for a sorcerer or AC for an oracle with the nature’s whisper revelation

  • Attack rolls, e.g. with smite

    • Note that performing a combat maneuver involves rolling “an attack roll and add your CMB in place of your normal attack bonus,” so it also does not count.

    • Completely tangential, but while we’re here: Whether or not a situation like smite, where you add both Strength and Charisma, would count as a “Charisma-based roll” is very unclear. There are very few situations where this comes up, but if it ever does I would almost-certainly count it, myself. As far as circlet of persuasion is concerned, the question is moot because whether it’s “Charisma-based” or not, it certainly isn’t a “check.”

  • Damage rolls, e.g. with Desna’s Divine Fighting Technique and a starknife

  • Saving throws, e.g. with divine grace

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  • \$\begingroup\$ Isnt this item much cheaper than single skill boosting items? \$\endgroup\$
    – Fering
    Commented Nov 10, 2018 at 20:56
  • \$\begingroup\$ @Fering No? A +3 competence bonus to a single skill would be \$bonus^2 \times 100\text{ gp} = 3^2 \times 100\text{ gp} = 900\text{ gp}\$, i.e. one-fifth the value of a circlet of persuasion. It’s certainly cheaper than getting separate items for each skill, to say nothing of other uses, but it isn’t literally cheaper than a bonus to a single skill at all. \$\endgroup\$
    – KRyan
    Commented Nov 10, 2018 at 21:44
  • \$\begingroup\$ Each skill boosting item requires an item slot in which to use it dont forget, so double the price to make it slotless. \$\endgroup\$
    – Fering
    Commented Nov 10, 2018 at 21:48
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    \$\begingroup\$ @Fering One, that rule is atrocious, never should have seen print, and should certainly never be followed. It is awful for the game. Wizards of the Coast realized this and amended the rule in Magic Item Compendium, but Paizo doesn’t understand their system and not only reprinted it and did not amend it, but has doubled-down on it. That doesn’t mean they are right; it’s a prime example of how poorly they understand their own system. Please do not enforce it. Two, even the official rules allow combining items for +50% costs after the first, so not double. Three, we could use multiple slots. \$\endgroup\$
    – KRyan
    Commented Nov 10, 2018 at 21:53
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    \$\begingroup\$ @Fering At worst, a circlet of +3-competence-bonus-to-several-skills would cost 3,600 gp for three skills, and 4,950 gp for four skills. There are only seven Charisma-based skills in the game, so if we’re only talking about skills you only save money here if you care about literally half of the Charisma-based skills in the game. Buying in bulk is supposed to result in savings. \$\endgroup\$
    – KRyan
    Commented Nov 10, 2018 at 22:00
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every check based on Charisma.

From pure charisma checks to charisma based abilities checks like intimidate, diplomacy and so on. This bonus apply even to charisma based check like concentration how you can clearly see in this other question here on RPG stack exchange.

Charisma-based checks

In addition to all of this, if you have a special abilities or some variation like the disable device skill based on charisma (this is just an example) you will apply the bonus from the circlet on every disable device check.

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  • \$\begingroup\$ If you read my answer is pretty clear i'm talking of "ckecks". I'm writing only about checks and nothing else :) \$\endgroup\$
    – Mouza
    Commented Nov 11, 2018 at 8:28

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