Hiya!
I am wondering if the Help action, taken as an action in combat, is automatic?
To clarify, if a PC or player controlled entity, like a familiar for example, can take the Help action then there is no DM ruling or consideration required on whether you can in fact "help" in these particular circumstances?
I bring this up because of considerations like the following. Ok, I Help him with his sneaking {dex (Stealth) check}. Possible DM response: Yeah how, exactly, do you do that? Ok, I move my invisible familiar here (within 5 feet of the attacked creature) and Help Goosh (the Fighter). Possible DM response: Yeah how, exactly, does your invisible familiar do that?
The PHB RAW are on p. 192:
Help is in fact presented and detailed in the rules so I would assume that even if it sounds odd or implausible that my expenditure of an action can in some way help, the fact that I can mechanically expend the Help action is enough to grant advantage.
If you could please educate me with your thoughts and experiences of using/adjudicating Help in game so I understand better or more fully I would be grateful. Thanks.
Here's how it would play out in my game:
Player: Ok, I Help him with his sneaking {dex (Stealth) check}.
DM: Yeah how, exactly, do you do that?
Player: Ok, I move my invisible familiar here (within 5 feet of the attacked creature) and Help Goosh (the Fighter).
DM: Ok, your familiar suddenly pops into existence right in front of the creature, screaming "BOO!!!". The creature is taken aback at the sudden appearance of a crow in front of him. Go ahead, Goosh, do your thing with +2.
This does two things: Lets the player get his 'Help' action off, and also teaches the player to be more specific.

When I DM, if my players don't give me specific info, when it should be obvious that I'm asking for it, then I get to 'fill in the blanks'.
If a player just says "I open the door", then I make the assumption that the character is opening the door....duh. But if the party thief just heard talking on the other side, and still says "I open the door", without any specifics, I'll assume they are opening the door...normally. If the player wanted his thief to try and open the door slowly and quietly so he could peek in, he should have said so. He's playing the thief. I don't know what the player is thinking; maybe he was thinking of throwing the door open quickly to startle the people on the other side, maybe he was thinking of opening it nonchalantly so as too make it look like he is supposed to be here, or...who knows? The player should know. If he doesn't, well, I just kinda make something up.
So, yeah. There's my 2 coppers.
^_^
Paul L. Ming