Improved grab while being grappled

Question

I was doing a small thought experiment yesterday in regards to what would happen if a grappling orientated creature (with the improved grab ability) is grappled himself.

The rules for improved grab from the SRD state that (emphasis mine, partial citation):

A successful hold does not deal any extra damage unless the creature also has the constrict special attack. If the creature does not constrict, each successful grapple check it makes during successive rounds automatically deals the damage indicated for the attack that established the hold. Otherwise, it deals constriction damage as well (the amount is given in the creature’s descriptive text).

However, in the event that such a creature got grappled himself (by another character/creature) and performs the 'damage your opponent' option of grappling:

While grappling, you can deal damage to your opponent equivalent to an unarmed strike. Make an opposed grapple check in place of an attack. If you win, you deal nonlethal damage as normal for your unarmed strike (1d3 points for Medium attackers or 1d2 points for Small attackers, plus Strength modifiers). If you want to deal lethal damage, you take a –4 penalty on your grapple check.

The creature would not do any natural attack damage as the creature did not initiate grapple himself. Therefore, the only damage the creature could do would be the 1d3 (if medium) + strength.

(Actual question) Consequently, does it make sense for such a creature to first try to 'escape the grapple', prior to attempting to initiate grapple (allowing it to use improved grab in subsequent rounds)?

Answer 1

On this particular topic you should judge rules yourself (you may call it homeruling it).

Rules for Improved Grab aren't clear enough and with a lack of example of play section tied to them there is no certain RAI. RAW may be read in different ways and which of them is "right" is up to you.

First questionable case is the part in the description, you have bolded. It is unclear what the word "automatically" even doing there. You inflict that damage by winning a chek, not just every round or something. Was it mentioned to say something to us?
If we ignore it and just go with "each successful grapple check deals the damage indicated for the attack that established the hold", we are left with the analogue of Constrict, which is also a common battleground for people with different opinions and rulings.

Constrict (and, depending on the above, natural weapon damage aspect of the Improved Grab) may be interpreted in two general ways:

1. Every successful grapple check inflicts damage.
   Most people, more or less, stick to this interpretation. This is because the definition states "grapple check". So it is every grapple check. This has it's downsides since when you, for example, avoid any attempt the opponent tries by initiating opposite grapple check, you actually make successful grapple check. You also make successful grapple checks when you successfully try to draw a light weapon or to move the grapple.
   Some people rule, that Constrict triggers from grapple checks initiated by the creature with it only. So trying to damage constrictor through grapple won't at least result in "retributive" constriction damage on a fail.

2. Every successful grapple attack inflicts damage.
   This point is based on the rulling, that Constrict is a separate option in If You’re Grappling. Basically, it lets you damage your opponent with a constriction damage instead of unarmed damage. Here is an example of such interpretation, which is, unfortunately, written in russian.

   • If you accept Rules Compendium as a reliable source, then this is true for both Constrict and Improved Grab, as Rules Compendium changed the wording for both abilities to say "successful grapple check to deal damage". So now it certainly is not every grapple check.

Second issue with the Improved Grab is the following. It states that grapple can be conducted normally or abnormally. What is unclear is where this difference ends.

1. One may rule that all the difference is described within the confines of the same (second) paragraph. So third and forth paragraphs apply to both normal grappling (modifying it) and single limb option.
   So the creature featuring Improved Grab may use the sentence you have bolded, for example, without taking -20 on the grapple check. It looks nice, as it would be realy stupid if the bear which has grabbed you with his claw will suddenly be restricted to damage you with non-lethal unarmed damage via grapple checks. And this interpretation supports that it may use his natural weapons either in addition or instead (depending on what you think on the first issue) of unarmed damage.
   This interpretation doesn't look reliable though, as it highly doubtable that the last paragraph applies to normal grappling. Being able to carry opponent away without restrictions is naturally expected from the single limb option, but not from normal grappling. There is some related research from this site.

   • Again, if you accept Rules Compendium as a reliable source, then you may stick largely to this interpretation. Rules Compendium omits the line about being able to move freely, and reorganizes whole definition. Now it supports the part about using natural weapon's damage in a Damage Your Opponent option, but makes free movement accessible through single limb option only (not being grappled).

2. You may also rule, that creature either can grapple normally (and normally from all respects), or go for a hold (-20 on the check, isn't considered grappling, can damage an opponent with or with addition of natural weapon, can carry opponent away).
   While this is kind of ugly, this option has less contradictions within itself and is supported by Scorpion's Grasp feat (Sandstorm, p. 52). While the feat can't actually say how does Improved Grab work, it is helpful for reference and showing designers' intent.

So, to your actual question.

The answer depends on your ruling on the second issue.

• If the "hold" referred to by Improved Grab is single limb option, then yes, the creature must first escape the grapple somehow to not be considered grappled itself before it can utilize options granted by single limb option.
  Note that it is possible for one to rule, that the creature can just win opposed grapple check at -20 and establish the hold. Not necessarily must creature leave the grapple entirely first.
• But if you rule the first way, then it should be able to just use the Damage Your Opponent option and deal its natural weapon damage (with any natural weapon suitable for Improved Grab) or its unarmed damage + natural weapon damage. Or, maybe, its unarmed damage + natural weapon damage + constriction damage, if it also can constrict. In that case it hasn't much reasons to try to escape.

Answer 2

If a creature with the special ability improved grab wants to automatically deal damage damage on subsequent rounds when it makes grapple checks, the creature must start the grapple using the attack linked to the special ability improved grab

The special ability improved grab follows rules that are specifically different from the more general rules for grappling. These rules include the following:

If the creature does not constrict, each successful grapple check it makes during successive rounds automatically deals the damage indicated for the attack that established the hold.

If the creature did not use the attack linked to the special ability improved grapple to establish a hold, the creature just doesn't deal this damage. Thus the above effect can't apply if the creature is itself grappled first; the creature must free itself from such a hold and start its own hold with the linked weapon and the special ability improved grab if it wants to generate the above effect.

Therefore a particularly skilled (or brave or foolhardy) PC could attempt to grapple a creature with the special ability improved grab before the creature grapples the PC in an attempt to negate the creature's extra damage during grapple checks. (My suspicion is that when the core rules were written the developers considered the possibility of a PC engaging such creatures in wrestling contests first remote, hence their leaving that possibility unaddressed and making these rules slightly counterintuitive.)

Answer 3

The larger implied question is

Can you start a grapple when you are in a grapple?

There isn't anything stating you cannot start a grapple while grappling, however, the options when you are in a grapple are fairly limited. In most cases, there would be no benefit as well. If a creature has Improved Grab, however, since one option is to attack with a natural weapon, they could follow through with starting a grapple.

In the scenario described, a creature with Improved Grab and Constrict when grappled may attack with a natural weapon, and if it hits, deals damage and from Improved Grab gets a free "start a grapple", and if it has Constrict, deals Constrict damage. The creature deals the natural attack damage plus Constrict with each successful successive grapple attempt.

What the creature can't do is take the -20 penalty to be not grappled, or rather would not benefit, since it is already in a grapple, without escaping from the grapple first.

Thus if you rule you can start a grapple while grappling

does it make sense for such a creature to first try to 'escape the grapple'

Not really.

Pros: Creatures with Improved Grab/Constrict can benefit even if another opponent starts a grapple with them.

Cons: "Starting a grapple" when grappled doesn't really make sense, much in the same manner tripping a prone opponent doesn't make sense. One could argue this is a special case (Improved Grab) due to the physiology that generally accompanies the ability.

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However, (in stark contrast) I don't see denying a grappler from starting a grapple against a target they are already grappling as an unreasonable ruling, even though there is no rule to cite for this. (Similar to limiting a prone target from being tripped.)

If you choose to rule a combatant with the grappled condition can't start a grapple

does it make sense for such a creature to first try to 'escape the grapple'

Yes. It would benefit the creature with Improved Grab and Constrict to escape the grapple first.

Pros: "Starting a grapple" makes more grammatical sense in this ruling and it simplifies potentially awkward rulings on who or what can be grappled according to physiology and position.

Cons: Removes an iconic and powerful feature from a foe, albeit only under this condition.