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The Help action is described in Chapter 9 of the PHB (emphasis mine):

You can lend your aid to another creature in the completion of a task. When you take the Help action, the creature you aid gains advantage on the next ability check it makes to perform the task you are helping with, provided that it makes the check before the start of your next turn.

Alternatively, you can aid a friendly creature in attacking a creature within 5 feet of you. You feint, distract the target, or in some other way team up to make your ally's attack more effective. If your ally attacks the target before your next turn, the first attack roll is made with advantage.

At first blush, one might assume that these rules for the Help action are self-contained and everything needed to adjudicate the action can be found within the section.

However, Chapter 7 contains he rules for "Working Together" (emphasis mine):

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.

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.

I am not sure how to understand the "In combat, this requires the Help action" from Working Together and the "Alternately" from Help. Is it that:

(a) What would normally be considered Working Together is, in combat, considered the Help Action instead; only the rules for Help, not Working Together, apply in that case.

(b) What would normally be considered Working Together is, in combat, considered the Help Action in addition; the rules for Help and those of Working Together apply in that case. In particular, in combat, you can Help someone only with an ability check you would be able to attempt alone, and you can Help someone attack a creature only if you would be able to attack that creature alone.

(c) As (b) for ability checks only, but alternatively when you are aiding a friendly creature in attacking another creature, the rules in Working Together are superseded. Lending aid in combat for ability checks follows the rules for Working Together, but lending aid to another creature specifically to attack a creature is an exception such that only the second paragraph in Help applies.

For example, consider a wizard with proficiency in thieves' tools and a familiar.

Can the familiar assist (give advantage to) the wizard in picking a lock? Outside of combat, no - the rules for Working Together require that the helper be able to perform the action alone. If, however, the attempt to pick the lock happened within combat, then under scenario (a) the familiar would now be able to assist while under (b) they still would not.

Can the familiar assist (give advantage to) the wizard in attacking a creature? If the wizard is attacking, by definition they are in combat. In this case the familiar could assist in scenarios (a) and (c), but not in scenario (b), since it is itself incapable of attacking.

As @Dale M notes, the consensus on this site is certainly that familiars can perform the Help action when their wizard attacks. However, this highly upvoted answer does not even mention the Help action's relationship to Working Together, and instead relies on a JC tweet for justification (to be fair, the answer is from August of 2016). I am interested in an answer that specifically explores the relationship between Help and Working Together, and if possible relies on RAW without JC tweets.

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Help and Working Together are independent but overlapping.

I'll provide my answer, then my reasoning.

The Working Together rules are part of the overall rules for ability checks; the restrictions it defines are the general rules that are in place, including the rule that helping with an ability check can only be done by a character who could normally attempt that check.

Help is one of the actions available in combat, and it lets a character do one of two conceptually related but mechanically distinct things: assist with an ability check (using the Working Together rules) or assist with an attack, using the rules set out in the Help action.

Characters using Help in combat to assist with an ability check follow the Working Together rules, and so (for example) a character without proficiency with thieves' tools can't use the Help action to assist another character in picking a lock during combat.

Characters using Help in combat to aid an ally in making an attack follow the rules in the Help action -- they must be within 5 feet of their opponent, and the attack must happen before their next turn. No other restrictions are listed.

Reasoning

This answer follows from:

  • The rules text for Working Together and the Help action.
  • The rules text that states that attacks are not ability checks.
  • The lack of any more specific rules for ability checks in the Help action.

The Working Together rules (PHB, p. 175) are a part of the Ability Check rules (pp. 174-179); there's no reason to think they apply to attacks or saving throws:

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.

Attack rolls are explicitly not ability checks (PHB, p. 174):

The DM calls for an ability check when a character or monster attempts an action (other than an attack) that has a chance of failure.

This is made even more explicit in the Sage Advice Compendium (v2.6, p.9):

Are attack rolls and saving throws basically specialized ability checks? They aren’t. It’s easy to mistake the three rolls as three faces of the same thing, because ... they share the same procedure for determining success or failure. Despite this common procedure, the three rolls are separate from each other.

The SAC also explicitly states that a creature that can't attack can use the Help action to grant advantage on an attack to an ally (p. 17):

Can the familiar you conjure with the find familiar spell use the Help action to grant you advantage on your attack roll? A familiar can’t attack, but it can take non-attack actions, including Help. As the text of the Help action indicates (PH, 192), the action doesn’t require you to be able to attack; you simply need to be able to provide some sort of distraction.

None of the rules in the Ability Checks rules apply to attack rolls, including the Working Together rules. Attacks have their own rules (pp. 193-196).

The Help action does add one additional rule to the general Working Together rules (p. 192):

When you take the Help action, the creature you aid gains advantage on the next ability check it makes to perform the task you are helping with, provided that it makes the check before the start of your next turn.

This timing restriction doesn't affect the general rule about when characters can provide help with ability checks. The first part of the sentence just restates the general rule for Working Together. So there's no reason to interpret the Help action as saying that in combat there are no restrictions on what tasks a character can help with.

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Help is sometimes Working Together, and sometimes not.

Working Together is sometimes Help, and sometimes not.

Helping with an ability check is an example of working together; but Helping with an attack isn't. As you quoted in "Working Together":

Sometimes two or more characters team up to attempt a task. The character who's leading the effort [...] can make an ability check with advantage, reflecting the help provided by the other characters. In combat, this requires the Help action.

Working Together only applies to ability checks in specific -- that is to say, skill checks -- not to attacks.

Similarly, the Help action is specifically described in the "Actions In Combat" section of the rules, which naturally doesn't apply when you're out of combat.

So you have three scenarios:

  1. It's in combat, and you want to assist with an ally's attack. That's just the Help action, but not working together, since it's not an ability check.

  2. It's out of combat, and you want to assist with an ability check, such as treating the victims of a plague or tracking a beast. That's just working together, but not the Help action because you aren't in tactical play at the moment and aren't tracking specific actions. (And those tasks very well may take more than a few seconds; you're talking about working together for possibly hours with a single roll!)

  3. When in combat, you want to work together to attempt an ability check that you can reasonable perform in a single round, such as lifting a gate or stabilizing a fallen ally. In that case, it's a special use of the Help action. The two mechanics overlap in this one specific situation, and the Help action makes a point to explain how that works.

The rules don't really go into how to handle helping with a more long-term task that you're trying to do when combat breaks out; depending on the task at hand, you might be able to interrupt it for a minute to go have a fight and then come right back to it, or you might need to use your turn every round to continue performing the task -- it's not really defined and it's such a corner-case that it probably shouldn't have a specific rule.

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To answer your question(s) first, as with any rules in D&D 5e they all apply, and specific overrides general in a cascade, though in this case this is not required. Going through your highlights in the rules text one by one shows there is no contradiction, no "either/or", they all apply at the same time.

"Alternatively"

Chapter 9 is on Combat and the quote is from the "Actions in Combat" section and describes using the Help Action in combat.

This means the rules here do not apply outside combat, except maybe as a reference for the intent of the other help rules, not least because you can only take Actions in combat.

The "Alternatively" used in this section is to distinguish between taking the Help Action to aid someone performing a task using an ability check, and taking the Help Action to aid someone to make an attack roll.

Why a distinction? They are different uses of the same Action, with different rules. For instance there is no range given for the Help Action when aiding someone in a task requiring an Ability Check, it is down to the DM to adjudicate if the description and circumstances of the help given warrants granting advantage. However there is a 5' range given for the aid given to an attack roll.


"In combat, this requires the Help action."

Chapter 7 is on "Using Ability Scores:" and the rules here describe the general rules for the use of ability scores to perform tasks.

This specific quote states the general rule that in combat, where creatures have to follow the combat action economy, aiding someone requires the use of the Help Action. Outside combat there is no such thing as the Help Action, the combat action economy doesn't hold, it is just helping someone.

This does not override or contradict the first rules quoted in the question above.


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

Also in Chapter 7 on "Using Ability Scores:".

This is a general rule, not overridden anywhere else in the help rules, that clearly states that the creature offering aid should be able to perform the task they are helping themselves, in whatever circumstances, combat or not.

This means that RAW, a creature that cannot attack, cannot aid in an attack. A creature without thieves' tools proficiency cannot aid a lockpicking attempt that requires the proficiency.

Again this does not override or contradict the other rules quoted in the question above. They all work, all at the same time.

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    \$\begingroup\$ One part of this answer seems odd to me: "a creature that cannot attack, cannot aid in an attack." However the Help action states that you are doing nothing like an attack at all but instead you "feint, distract the target, or in some other way team up to make your ally's attack more effective". I think it would be good to establish that distracting a target requires being able to make an attack and thus, if I read this right, you would conclude that familiars cannot use the Help action to grant advantage to an attack at all? \$\endgroup\$ Commented Jul 6, 2021 at 12:08
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    \$\begingroup\$ Also, the general consensus is that familiars which can’t attack, can Help another attack. \$\endgroup\$
    – Dale M
    Commented Jul 6, 2021 at 12:19
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    \$\begingroup\$ RAW the general rule for helping in any situation is "A character can only provide help if the task is one that he or she could attempt alone." This is not overridden in any way by any specific rule for the Help action in combat. If a creature can't attack it can't help someone else attack. \$\endgroup\$
    – Protonflux
    Commented Jul 6, 2021 at 15:42
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    \$\begingroup\$ The general rule for helping is for ability checks. The second clause of the Help action isn't a special case of that rule; it's a different rule for helping with attacks. \$\endgroup\$
    – Marq
    Commented Jul 6, 2021 at 16:00
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    \$\begingroup\$ The issue isn't combat vs. noncombat. The issue is ability checks -- which is what the Working Together rules cover -- versus attack rolls. Attack rolls are not ability checks. So the second clause of the Help action isn't about ability checks at all, and the restrictions in Working Together don't apply. \$\endgroup\$
    – Marq
    Commented Jul 7, 2021 at 10:43

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