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In the Curse of Strahd, the Barovians and Vistani hold the superstition that Ravens carry the souls of the dead with them, and that harming one is bad luck.

Would Barovians and Vistani be more easily intimidated by a wizard with a raven familiar, and be more reluctant to attack that wizard? If so, how would this manifest mechanically for attack rolls and Intimidation (Charisma) checks?

Note: Because the familiar was summoned outside of Barovia, it is currently a fiend, not an undead. By RAW, if it is summoned within Barovia, or the wizard changes its form, it will become an undead. I am unsure how that physically changes the familiar, but I would have it be evidently undead, thus solving the problem.

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  • \$\begingroup\$ I removed the second question because we only allow one question per post. If you want to ask another question about how the raven familiar can help with different locals, you can just post it as a separate question. Thanks! \$\endgroup\$ – SevenSidedDie May 8 '17 at 4:39
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This is largely up to the individual DM, but I've had a stab at how the rules might influence your decision. On page 28 of Curse of Strahd, the superstition says:

  • Ravens carry lost souls within them, so killing one is bad luck. (The ravens don't carry souls within.)

The superstition is that killing a raven is bad luck, and carrying a lost soul is kind of creepy. (Also, this is something they believe that isn't true; the ravens don't carry souls.) This allows a fair bit of latitude around how individual Vistani feel about ravens; they may be impressed by them, see them as good omens, or find them creepy and want to avoid them. In the right circumstances I would give a wizard advantage on a Charisma (Persuasion) check or Charisma (Intimidation) check for having a raven familiar, but it would have to depend on their actions and the individual in question.

I wouldn't impose any penalty on Vistani against attacking the wizard, though I might restrict the actions they take a little; one with an area attack might avoid using it if it would hit the raven, for example. Since wizard familiars can't attack, it's not going to be a big problem.

On the undead raven: that's a cool idea, but it'll be a world-building decision, not a rules one. The spell description for find familiar specifies that the familiar takes "an animal form you choose", so its up to the caster what the familiar looks like. The change specifically says familiars are immune to being turned, which indicates its mostly for flavour - like other familiars, its a spirit creature which takes physical form, it's just that in Barovia the spirit comes from the underworld (or perhaps the mists?) instead of from the feywild or the upper or lower planes.

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Yes, the familiar will help you

Due to the rule on Working Together, the raven familiar is capable of taking the Help action, which grants you Advantage on any check you wish to perform, within reason.

PHB 175, Working Together

Sometimes two or more characters team up to attempt a task. The character who's leading the effort -- or the one with the highest ability modifier -- can make an ability check with advantage, reflecting the help provided by the other characters. In combat, this requires the Help action (see chapter 9).

Meanwhile, the text on Find Familiar says:

Your familiar acts independently of you, but it always obeys your commands. In combat, it rolls its own initiative and acts on its own turn. A familiar can’t attack, but it can take other actions as normal.

This means the familiar is capable of all non-Attack actions, which includes the Help action.

This can also be performed by any familiar of any other form, not just a raven. You would still have to justify how it helps, of course, and doing so is easier if you are in possession of a creature the enemy is already afraid or wary of.

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Ask your DM

This isn't a simple yes or no question. The title "would a Raven familiar help me during interactions" implies you are asking as a player. But social interactions in D&D are completely up to your DM. As a player, you can think something would work, but you can't guarantee that, since your DM can think otherwise.

Let your character do the investigation

In the Curse of Strahd, the Barovians and Vistani hold the superstition that Ravens carry the souls of the dead with them

How do you know that? Have you read the Curse of Strahd book itself? As a player, to spoil all the fun?

More importantly, how does your character know? Did he read that in a library years ago? (if so, did your DM ask for an Intelligence/History check?) Did someone say so? (if so, how can you be sure they didn't lie?) Let your character investigate. Experiment, dare, make mistakes, try different things. What makes every D&D game unique, is that every DM can lead the adventure their own ways.

If you are the DM

Let's suppose you ask this as a DM. There are actually several different questions here:

  • Should the superstition against ravens affect Barovians' behavior? How exactly?
  • How can it be represented mechanically?
  • Does the Barovians' superstition affect combat?

How Barovians' superstition affect their behavior?

There can't be simple answer, because people differ, and because the answer heavily depends on how does the DM interpret the setting. As a DM, you should figure it out yourself. There are brave NPCs and there are cowardly ones. They can't have identical behaviors.

My guess that incidentally showing the raven won't help a PC in social interactions with Barovians, but will actually make things worse. Imagine someone incidentally makes you break a mirror in Friday 13th. If you are superstitious, you can be frightened because "breaking a mirror is bad luck", but probably you will be offended and angry in the first place.

Besides combat, how do you force someone to harm the raven? The superstition is against killing ravens, not just watching them. Moreover, in D&D world many people can know what wizard's familiar is. They will know that the raven isn't actually a raven but a celestial, fey, or fiend.

Do the Barovians' superstition affect their combat?

That's actually easy. There are strict rules for combat in D&D. The raven familiar has no "gives an advantage on attack rolls against Barovians" feature in its stats block. Neither Barovians have explicit disadvantage on attack rolls against ravens. As a familiar, it still can do the Help action, but just being a raven doesn't give it more features in combat.

Carrying a raven does not give you advantage on your attack rolls. After killing the raven, an NPC might have concerns for their luck. But that will happen after the combat and shouldn't affect the combat itself.

How can it be represented mechanically?

Instead of "+2" situational modifiers, 5e has advantage/disadvantage mechanic. If DM thinks the situation is more favorable to you, they say "make a X check with advantage", or "make an attack roll with advantage". Advantages do not stack, so mechanically one or several favorable factors all will have the same effect.

Considering Intimidation checks, I'm not sure a familiar would help the wizard. PHB page 175 "Working Together" says that

A character can only provide help if the task is one that he or she could attempt alone.

I don't think a raven familiar alone actually can intimidate an adult reasonable human without attacking him (keep in mind that familiars can not attack).

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(I started writing a comment but it got too long)

Yes, but

Yes, your familiar may help you and give you advantage to some rolls.

HOWEVER, Barovians and Vistani are superstitious (with good reason) therefore parading around with a raven may (and should) trigger more than the occasional disadvantage to the roll.

Your GM will make the call, and expect different reactions from different NPCs. The raven is cool but in Barovia may be a liability. Some people may think it is a spy of Stradh and act differently around you (and your familiar) because of that.

Otherwise

In most "traditional setting" your familiar may help you, with ultimate determination on whether it helps or not is up to the GM.

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  • \$\begingroup\$ Why would a raven add disadvantage? They are not bad luck or considered an ill omen in Barovia. \$\endgroup\$ – LegendaryDude May 9 '17 at 20:22
  • \$\begingroup\$ That they can serve as spies for SvZ and that they are believed to hold the souls of the dead may not make people want to be your friend and help you. My point is that they can help sometimes and can be hindrances some other times. Work with your GM. \$\endgroup\$ – JP Chapleau May 9 '17 at 21:13
  • \$\begingroup\$ I am asking from the perspective of a DM who has run Curse of Strahd. I won't spoil anything here but I think your last comment is incorrect based on what I know of the adventure. \$\endgroup\$ – LegendaryDude May 9 '17 at 21:37
  • \$\begingroup\$ Again, if you read my comments, I do not make any definitive or categoric statement. I recommend the player work with the GM and that there will be times when a familiar can help and times when it will hinder. \$\endgroup\$ – JP Chapleau May 9 '17 at 21:45

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