[RPG] Does a Wizard’s Familiar grant advantage on every roll

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We're a new group playing DnD 5e. Three of us have no prior experience (and I'm one of them, never played the earlier editions) whilst two of us have some to good experience with other editions.

I'm DMing Rise of Tiamat and I'm really struggling with giving the players any kind of challenge. We've got a Paladin with Sentinel and a Halberd, almost stopping everything in its tracks when they attack, a Wizard with Fireball (he might have found a spellbook), Minor Illusion and the Tiny Hut spell (which really messes up any kind of surprises I have in store for the night), a Druid which doesn't do much and a Rogue which died last session because of PVP (he got the option to sacrifice one player by an evil fountain spewing blood, he took it – and it didn't pay off in the end).

Just a bit of context.

My question is this: our Wizard is because of his familiar (a rat which he has on the inside of his robe) constantly throwing advantage on all of his D20 rolls. I said I won't allow this in the future sessions because the familiar needs and initiative, and also needs to somehow confuse or do whatever with the mobs to allow advantage.

He does, however, claim that the familiar gives him an advantage on all skill checks as well, in and out of combat. Is this according to the rules?

Best Answer

Not exactly. The rules on Working Together in order to give advantage are as follows:

A character can only provide help if the task is one that he or she could attempt alone. For example, trying to open a lock requires proficiency with thieves’ tools, so a character who lacks that proficiency can’t help another character in that task. Moreover, a character can help only when two or more individuals working together would actually be productive. Some tasks, such as threading a needle, are no easier with help.

In other words, his familiar can only help him if the task is one that

a) The familiar is capable of accomplishing by itself, and

b) The task is one where the familiar's help would actually assist the character in completing the task.

It's up to you, of course, to decide if a given task satisfies these requirements. But you certainly shouldn't just let him gain advantage on every check automatically.