Dougal's Response

Dougal had made a "lucky" saving throw against charm  (he rolled a natural 20) - but in retrospect, maybe it wasn't so lucky. He'd have done far better failing it and telling them everything without being tortured!
Anyway, just before getting the list of questions from Darrell, I had sent this:
No idea what has been happening to Dougal all this time, or what sort of conditions he is being held in - but I hope that he would have taken any opportunity to loosen or at least test his bonds to see if he could escape at all.
Otherwise, as previously said, he will try to take in as much information about his captors and surroundings as possible - while avoiding thinking anything about the party or any prior events by singing nonsense songs in his head and incorporating his observations into them. 
That email crossed paths, as it were, with Darrell's list of interrogator questions, and Darrell replied:
Your personal update has just arrived.........getting sticky for poor Dougal I am afraid.....
To which my response was:
I fear things are about to get even stickier... 
Dougal will not answer any of the questions, and won't even think about them. He'll just start singing his silly songs out loud to stop him from saying anything else - and to mask his thoughts, and his pain. 
Whether he can stand up to torture and having bits cut off him I don't know - but he will certainly try. (His Wis is 15, Con is 10).
Poor Dougal.
Darrell then asked for Dougal's charisma (as a representation of Willpower) , to which my response was:
Charisma 9.
If he can't stand up to torture and breaks, then there are just two questions that he will try really hard to lie about: He'll say that we have no idea where the White Tree is - why should we? (No Wyldwood clerics in the party, or anyone who has started the pilgrimage). And for the item brought from White Beach - don't know what it was exactly because it was in a box, but we were told is was an Elven Manifest. Don't know why we were told to bring it here rather than the Elves carrying it themselves, but they kept a close eye on us through Elven 'minders' on the ship. As for the other questions - well, I guess it depends on how far he has been 'broken'.
which led to:
Unfortunately Dave - these arent very nice people....
Dougal lasts for about 20 minutes, by which time every bone in his left hand and wrist has been reduced to splinters...and somehow you cannot pass out.. 
...you cant remember much about what you tell them... but you are babbling everything, anything you think they want to hear....would probably sell your Mother if she was there..... 
...then you pass out....