Once I get to the "talking" stage with the trio in Cockerel Forest, they won't let me help them. I've read online that this can happen if the Watcher has the "Cruel" reputation, but mine is 0.

Can someone tell me if I'm missing something or my information was inaccurate/incomplete?

Can you remind me what island that's on? Or if you don't remember that, where on the map you were?

Crookspur Island, north-west side.

Hmm. I didn't know it was possible to aid them, as I always get into a fight (and they drop a very nice flail, Ball and Chain, if it's the group I'm thinking of). I've now played 4 full games, and don't think I ever had points in Cruel--and yet fights always broke out.

I wonder if a Watcher w/ decent Diplomacy would change that situation from the start? A skill I've always ignored for the most part (usually in favor of Insight).

Yeah, I've been successful on that check early on, and they agree to talk to you... according to guides online, you're then supposed to have the option of aiding them if you don't have points in Cruel. But the dialogue option isn't there. :(

Yeah, that's what I'm looking at -- the dialog option "Cathŵenna will ask for your assistance..." never appears.

So if I'm reading that right, you first made the Watcher-only Insight (10) check, and then you made 1 of these 3 checks: Bluff (12), Diplomacy (14), or Intimidate (16)? I'll have to assume those are party-assisted checks.

Are you trying to avoid a tough fight or simply role-play (playing a druid, perhaps, or a good-aligned paladin)?

Just role-playing. Not too concerned about the fight.

Yes, that's correct. I made those checks (tried all of them), at which point it takes you out of "scripted" mode and into iso view, and you begin an actual dialogue. According to the reference, the ex-slaves should ask for 6k gold... but that never happens. I ask if I can help them, and they say no.

Just a slight update, as I finally had a game where this worked out w/out a fight. I think that Gamepedia info is slightly incorrect. I definitely didn't start w/ any Watcher-only Insight (10) check, but I did have a Druid w/ high Diplomacy. I ended up giving them 6k gold for the Ball & Chain flail. I wonder if you need a Ranger or Druid for your main PC??

I know it's an old thread, but that's the one google gave me, so I leave an answer there, if anybody do the same search for the same answer.
The gamepedia was wrong, you need a diplomatic check to make them stand down to be able to offer assistance. This is reflected in the dialogue "that's the second time you offer your help...". I assume it also need to be a watcher only diplo check, but I have no proof of that one.
If you make them stand down through intimidate/bluff, the conversation end when you offer your help and you can't get a diplomatic solution.

I edited the wiki so hopefully that won't be an issue in the future.