By the RAW I don't think Rake can ever be used. You "obviously" can't use it when you Pounce since you must start your turn grappling to use Rake and explicitly can't start a grapple and Rake on the same turn.
Even if you do start your turn grappling you probably can't technically use the two free attacks from Rake since using extra attacks generally requires a Full Attack. The Rake attacks need to be used against a grappled foe, and you won't be able to both maintain the grapple and make a Full Attack unless you have Rapid Grappler (which most monsters in the Bestiary don't have). Rules Text: "If you get more than one attack per round because your base attack bonus is high enough (see Base Attack Bonus in Classes), because you fight with two weapons or a double weapon, or for some special reason, you must use a full-round action to get your additional attacks."
In practice I allow Rakes on a Pounce and also allow free Rake attacks once per round starting in round 2 of a grapple being maintained. I would allow the monster to use whatever options normally exist on the check to maintain the grapple and apply damage, a pin, etc as normal before attempting the free Rakes. For instance, a lion who Grabbed you with his Bite could grapple you for damage and inflict Bite damage and then also Rake you twice for Claw damage. Alternately the lion could Pin you and then Rake you twice (which is probably more dangerous really)
My big grappling question is whether or not the Pinned condition needs to be maintained each round separately from the Grappled condition. What I mean by that is whether a creature pinning another has to select the "Pin" action each round while maintaining the grapple to maintain the pin or is free to select other options like moving the foe or causing damage. The answer to this could make an absolutely gigantic difference in combat, especially for creatures which have Grab but not Constrict or Rake. Owlbears would suddenly be a lot scarier, for instance.
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It is possible that Rake is intended to work in the manner you've proposed with a new "Rake" action being added to the usual list of actions available while maintaining the grapple (Move, Damage, Pin, and Tie Up). If so that seems really unclear from the RAW though, and the fact the text for Rake refers to the attacks as "free" seems to imply that you shouldn't have to sacrifice something else to gain them. I mean, if you give up the Bite damage you could normally inflict while maintaining the grapple with the "Damage" action for the chance to make 2 Claw attacks I wouldn't call that "free". I guess I should also ask whether you think the two free Claw attacks require attack rolls or just automatically hit and do damage if the grapple check is successful. I'd assume the former. I'll also ask if you allow Rake attacks during a Pounce. I do even though that seems to contradict the language in the Rake ability which says, "A monster with the rake ability must begin its turn already grappling to use its rake". I think whoever wrote that might have assumed we'd be smart enough to know that restriction only applies to the use of Rake while grappling rather than to the use of Rake while pouncing. I'm not really that worried about Rake though. I think it is pretty clear how it is "supposed to" work and even the difference between your interpretation and mine seems pretty minor to me.
I'm aware that the two checks needed to move from pinned to freedom was cut down to one in Pathfinder. I don't think it is clear from the RAW whether the Pin needs to be maintained from round to round though, especially in the light of 3.5 history. Paizo actually took the time to clarify that getting out of a pin only requires one successful check. I'd like it if they could also take the time to clarify whether you need to use the Pin action each round to maintain the Pin. There's really nothing in the new rules which implies this is the case, but every Pathfinder game I've played in has treated it that way. As a result, most monsters rarely use the Pin action, and monsters with Grab but not Constrict tend to get killed by full attacks from the grappled PC. I'm not saying that's right or wrong, just that it might change dramatically if an Owlbear could Pin you in round 2 and then Damage you in subsequent rounds without losing the Pin.
Now that I've started thinking about it a little more I'm also beginning to wonder how Swallow Whole should work in a world where a Pin doesn't need to be maintained. I'd assume that once you're swallowed whole you just have the grappled condition rather than the pinned condition since otherwise you wouldn't have a chance to cut your way out of the monster's stomach (something which is currently way too easy in most cases but should certainly be possible)
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Much misinformation in this thread already.
A creature with Pounce and Rake can indeed Rake on a Pounce.
You do *not* need to only be in a grapple.
The option to Rake after succeeding to maintain the grapple is in addition to the standard options always available to other creatures.
So, instead of Pin/Damage/Move, now you have Pin/Damage/Move/Rake.
And the Grab ability works differently from Bestiary to Bestiary. I can't recall the exact hiccup at the moment, but I believe it has something to do with the size of the creature capable of being grabbed.
Regarding Grab, there was a FAQ a while back based on a question I posted. Bestiary said that you could only use Grab on creatures smaller than you while Bestiary 2 said that you could use Grab on creatures of up to your own size. The FAQ upheld the rules from Bestiary 2 as the correct ones. Of course that size limitation is just the default and a specific creature's Grab ability might specify something different. For instance, my Feral Gnasher is Small but can Grab up to Medium creatures, and in a few levels he'll be able to use Grab on Large creatures too.
Anyhow, I'm not saying that a create shouldn't be able to Rake on a Pounce, just that it might appear that way based on the RAW for Rake. When the RAW and the way most people expect things to work aren't in alignment I think that's a great time for a FAQ. I think that whether or not you need to maintain the Pin is a much more important question than anything regarding Rake though. As I've said, there's really nothing I can find in the rules which seems to imply that you should need to use the Pin action round after round to keep somebody pinned, but I've never seen a DM who didn't play it that way. Maybe I've just played with 6 or 7 weird DMs and everybody else knows the right way, but from where I'm sitting it seems like there's some potential confusion on this issue.
Something else which has changed since 3.5 is that there don't seem to be any size limits on what you can grapple (not Grab, just grapple). Maybe that was intentional, or maybe it was just an omission.
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How can you rationalize this when Rake specifically states you cannot Rake and start a grapple on the same turn?Much misinformation in this thread already.
A creature with Pounce and Rake can indeed Rake on a Pounce.
You do *not* need to only be in a grapple.
When a creature with this special attack makes a charge, it can make a full attack (including rake attacks if the creature also has the rake ability).
I guess folks feel that the text in Pounce allowing Rake is specific text which trumps the general text in the Rake ability which requires you to be grappling to use Rake. Maybe that's true, and I've certainly always played it that way, but I've had DMs challenge it in the past due to the text under the Rake ability repeatedly mentioning grappling restrictions.
I'm still not firmly convinced that the "free" attacks from Rake aren't in addition to what you get from Move/Damage/Pin/Tie Up rather than in place of it. Granted, Rake says it offers a new "option" while grappling, but I'm not sure if "option" and "action" are equivalent here. For instance, I'd consider Constrict to be an additional "option" you have when you succeed on a grapple check using one of the grapple "actions". I wouldn't force a creature or character to use Constrict if he or she didn't want to (perhaps because they just wanted to Pin somebody without harming them). Similarly, I'd consider making two free Claw attacks with Rake to be an option you can choose to take advantage of or not when you start a round grappling rather than an alternative to the regular actions available during a grapple.
Being able to maintain a Pin from round to round without using the Pin action each round would be a huge change for many groups. I agree that there's nothing in the rules which implies you need to keep on using the Pin action, but I doubt that most people I play with would agree to change how things are done without some comment by Paizo showing this was an intentional change rather than an oversight. I did raise the idea during a previous campaign, but the DM dismissed it partially due to concerns that it would make the monsters too deadly. I'd feel a little guilty if we switched rules and people had some PCs die and then later on Paizo said it was just an oversight and you do indeed need to use the Pin action every round to keep somebody pinned.
I kind of wish that the pinned condition just gave you some big penalties on your actions rather than making you essentially unable to act. That's obviously a separate issue and beyond a "rules question" though.
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The big thing about Rake is this: It is not constrict. Constrict lets you deal damage just by making a grapple check, and does not care what you do with it. Rake cares, as you get two attacks, have to roll to hit, etc.
You only need to roll attacks for Rake during a Pounce.
If used as one of your options after succeeding on a grapple check, no attack roll is needed. That's what the CMB check was for.
Consequently, this also means you cannot Power Attack on such a damage roll (which I also see many ppl assume you can do).
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It seems pretty clear.
Rake grants you two free attacks during a grapple (or during a pounce attack)
Constrict deals damage on a successful grapple check.
Both are seperate from the normal grapple actions. Not a seperate choice instead of those actions. Nothing in the rules states that the two free attacks granted by rake are automatic like the rule for constrict does.
(Posting from my phone so I apologize for any errors and lack of quotes)
As far as I know you can Power Attack while grappling and receive the normal bonus to melee damage rolls. For some reason it seems that Power Attack doesn't get applied to Constrict and Rend though.
I agree with Lance that the intent of Rake seems pretty clear even though I think the wording is somewhat contradictory. Constrict has actually received some FAQ attention in the past, and I think it is one of the easiest parts of grappling to understand and apply now though I still very often see DMs get it wrong initially. Maybe there's some hope that grappling has been addressed somehow in Pathfinder Unchained. I kind of doubt it, but it would be nice if the grappling subsystem got some clarifications and updates since it is one of the more confusing areas of the rules in some ways.
Unarmed combat in d20 games has come a long way from the Pummeling, Grappling, and Overbearing tables in the 1e DMG. It seems like striking has gotten most of the benefit though. Even non-Monks can now punch and kick people using the normal combat rules and without consulting a special Pummeling, Brawling, or Martial Arts table. Meanwhile some folks have actually created flow charts to try to help people understand the grappling rules, but it seems like ultimately nobody can quite agree what those rules are.