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I don't see anything listed in either the Hellknight Commander's or Enforcer's description that says they lose abilities if they are no longer allied with the Hellknights in general, so I'd like to know if someone who has a Hellknight prestige class can defect (the best word I can think of right now) from the order and retain the abilities their PrC granted them?

For instance, if a Hell Knight has redeemed him/herself by one means or another, could they then join up with others who oppose Cheliax and use their incredible powers, insight, and knowledge of Cheliax to help their new comrades as a Double-Agent of sorts?

As a DM, myself and a player wanted to do this, I think I would allow it since it could add so much to the story; even though it might not actually be kosher according to the official PF rules or errata. Additionally, with the Unchained options for alignment, I think a Hellknight could redeem him/herself in this way without breaking the rules.

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Well, you are in luck as the Pathfinder Campaign Setting book "Path of the Hellknight" just shipped and I have it in my hot little hands.

The answer is "not automatically, but probably." To quote the book's section on Fallen Hellknights:

Fallen Hellknights: While playing an ideal Hellknight can make for a challenging and exciting character concept, so can playing a fallen Hellknight. A fallen Hellknight might be any character whose personal philosophy prevents her from obeying the Measure and the Chain. A Hellknight might come to struggle against her training and eventually decide to leave her order—likely making enemies of her former brethren. While falling from the Hellknights’ esteem might not come with the same strict and immediate ramifications as for a paladin who disobeys her deity, at the GM’s discretion, it might eventually result in the loss of Hellknight abilities. Hellknights who leave or are cast out should work with their GM to retrain, as detailed on page 188 of Pathfinder RPG Ultimate Campaign.

Basically, some Hellknight abilities are tied to the order, and plus it's a fairly non-Lawful act to leave your Lawful order, so in most cases you should swap those levels out for something else, but your GM is the ultimate arbiter of what powers you might lose or keep and what your options are.

Some of this isn't "rules" it's "society" - if you leave the Hellknights and keep wearing Hellknight armor, for example, you're going to get hunted down by pretty much all other Hellknights and staked to something unfortunate. If you were to stay in the order as a spy that might work, but that's super non-Lawful and note that most folks there can detect lies and chaos. So, still somewhat problematic.

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  • \$\begingroup\$ I do not have that book yet, but it sounds like it would be a great addition for my group this time! Thanks for sharing :) \$\endgroup\$ – Ev- Jul 5 '16 at 1:33
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Yes...

... if they still meet the requirements for the prestige class. Notably, neither actually requires the character to be evil, only lawful. Sure, you have to prove yourself to the Hell Knights for them to let you in, but once you've slain a devil while being watched by another Hell Knight that prerequisite is always fulfilled.

In other words, if the character's change of heart is Evil -> Non-evil, that's fine. If it's Lawful -> Non-lawful, they no longer meet the prerequisites and (I think they should) suffer consequences similar to a fallen Paladin in that they lose their divine abilities.

A monk has the same Lawful-only alignment restriction, and their unchained description reads as

Remove the alignment restriction. A monk who ever has a loyalty to chaos, imbalance, or closely related concepts becomes an ex-monk for as long as he has those loyalties.

which could fairly easily be applied to a Hell Knight as well.

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Yes

There is nothing in the rules that says you cannot leave the hellknights once you've taken levels without losing the benefits of those levels. This would be a fairly rare occurrence, since to get to a high enough level to even take those classes you've likely been working in close proximity to the hellknights for a while and get the gist of what they do, and if you swapped alignments, it'd be a little awkward what with the aura and smite abilities and whatnot.

In response to the second half of A McCurran's answer, RAW there is nothing that says they lose any of the abilities with an alignment change, they just couldn't take any more levels in the class because they no longer meet the requirements. In fact, a lot of the abilities for both of those classes seem to come more from training and willpower than external force (like a paladin's or cleric's powers), so losing the abilities wouldn't necessarily make sense.

But the key point here is that the rules seem light on this subject and the subject of prestige classes in general, so the exact specifics of what would happen would most likely be up to the GM.

Sidenote: there are Hellknight orders that are not primarily evil, Order of the Chain is LN and the Orders of the Godclaw, Nail, and Pyre seems to lean more towards LN/LG. The Hellknights as a monolithic group are far more focused on the ideals of law than of good or evil.

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