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At low levels in Rise of the Rune Lords our group got tangled up with a more powerful being than we expected (as few spoilers as I can get away with). Over the course of several rounds while the enemy taunted and ensorcelled us we realized that we weren't damaging it and had to change tactics.

Our witch cast every type of Evil Eye on it (though the important ones were probably -2 AC and -2 to-hit) and Cackled to keep them in effect. Our Monk grappled the Fine-sized flying creature then successfully pinned it. The Alchemist then tied it up. The Monk managed to maintain his grapple every round.

It was a Quasit Witch. Once it ran out of spells our Alchemist managed to kill it with a coup de grace with a Gnome Hooked Hammer.

Even with all of the hexes, grappling and binding our Samurai still had quite a bit of trouble hitting the thing. Did those maneuvers stack, and is there anything else we could have done to reduce its Dexterity or AC further?

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    \$\begingroup\$ For reference, >! at the start of a paragraph makes that paragraph a spoiler. \$\endgroup\$ – KRyan Feb 28 '17 at 19:16
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    \$\begingroup\$ Also, this arguably overly broad. Whether the things you did stack is one question (and a relatively simple one), while asking for additional options is a much more complex question that could probably better stand on its own. \$\endgroup\$ – KRyan Feb 28 '17 at 19:23
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    \$\begingroup\$ I'm a little confused still, if you are delivering coup de grace (because they are helpless after being bound), you automatically hit. Are you asking if the thing should be forced to surrender? The fact is, the Evil Eye and grapple/pin where superfluous after you bound the creature, it was helpless; but it would never be forced to surrender. If you meant should you pass DR, then no, DR is not affected by being helpless; it's innate; however, coup de grace gives automatic critical, which easily surpass (the typical) 5-10 DR. \$\endgroup\$ – Ifusaso Feb 28 '17 at 21:19
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About stacking

Yes, evil eye stacks with the pinned condition. The penalties are untyped and come from different sources, so they stack.

All told, you should be looking at −2 penalty from evil eye, a −4 penalty from the pinned condition, and it is denied its Dexterity bonus to AC by the pinned condition as well, potentially reducing the AC yet more.

About “helpless”

The rules for tying someone up only specify that it makes someone easier to pin, but the helpless condition specifies that a helpless creature is one that is “bound” (or several other things), so in answer to the title question, yes, the creature should literally have had the helpless condition, even though the rules for tying up themselves neglect to mention it. For the purposes of the rest of this answer, however, I will presume that the helpless condition was not applied for whatever reason, since if it is all of this becomes moot—against a helpless creature, you can coup de grace, which doesn’t even use an attack roll, automatically crits, and has a chance to flat-out kill the target even if the crit damage wouldn’t already have been enough to do that.

Additional options

As for more you could have done, an easy one is knocking the target prone, if it wasn’t already; that gives melee attackers a +4 bonus on their attack rolls. Another easy thing is flanking, since the target is pinned anyway; even if the second flanker didn’t even try to attack, he could have given the samurai another +2 bonus from the flanking. Finally, the last easy, everyone can do it thing I can think of is the aid another action, which everyone (aside from the samurai himself) could have been doing to give the samurai a +2 bonus each. With three such helpers, plus the flanking and prone bonuses, the samurai would have gotten an extra +12 on his attacks.

There is undoubtedly more you could have done, or at least someone could have done if they had the right tools, feats, or class features, but it doesn’t really matter. If you cannot hit a target with −6 or more penalty to AC while you have a +12 or more extra attack bonus, you shouldn’t be attacking, you should be running. Even if for some bizarre reason this thing was unable to escape that situation (which nothing that powerful should be without some kind of escape button, but whatever) and you actually managed to kill it, something that powerful is likely to have powerful allies, which may well mean someone will resurrect it and now it’s pissed at you personally.

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  • \$\begingroup\$ The pinned condition denies the creature its Dexterity bonus to AC, which is effectively treating the creature's Dexterity as 10. A creature with 16 Dexterity takes a -7 penalty from being pinned (-4 from pinned, -3 from the loss of Dexterity). If the monk had tied up the creature, then it would be helpless and have an effective Dexterity of 0. \$\endgroup\$ – Jon Claus Feb 28 '17 at 21:25
  • \$\begingroup\$ @JonClaus Right you are, got that conflated with helpless. \$\endgroup\$ – KRyan Feb 28 '17 at 21:35
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I don't know the specifics on the monster but having something tied down/helpless plus Evil Eye would seem sufficient [as KRyan explains: untyped penalties (and bonus) from different sources stack].

Perhaps you weren't applying all of the effects of grapple, it mentions what happens when you are 'grappled', 'pinned' and 'bound'(helpless)

Relevant quotes:

Once you are grappling an opponent, a successful check allows you to continue grappling the foe, and also allows you to perform one of the following actions (as part of the standard action spent to maintain the grapple).

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Pin: You can give your opponent the pinned condition (see Conditions). Despite pinning your opponent, you still only have the grappled condition, but you lose your Dexterity bonus to AC.

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Tie Up: If you have your target pinned, otherwise restrained, or unconscious, you can use rope to tie him up. This works like a pin effect, but the DC to escape the bonds is equal to 20 + your Combat Maneuver Bonus (instead of your CMD). The ropes do not need to make a check every round to maintain the pin. If you are grappling the target, you can attempt to tie him up in ropes, but doing so requires a combat maneuver check at a –10 penalty. If the DC to escape from these bindings is higher than 20 + the target’s CMB, the target cannot escape from the bonds, even with a natural 20 on the check.

What isn't noted specifically in the Grapple rules is that a 'tied up' creature has the 'helpless' condition which IS noted in the description of helpless.

A helpless character is paralyzed, held, bound, sleeping, unconscious, or otherwise completely at an opponent’s mercy.

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