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[Brotato]

Yeah, it sounds like your Honchos are still too weak to mount a full on assault of whatever mine he gets sent to. Your best option for a break out is pretty much right away. If you wait too long they'll keep your character half starved, reducing your stats to the point where escape is impossible. Of course, to escape you'll actually need your guy to have some lockpicking skill. If he doesn't have it, your next best option would be to quickly train someone else in lockpicking+sneak and hope they can get close to him later.

[NullForceOmega]

If you're really desperate to get your guy out quickly there's a kind of exploity method you can employ.  Once you get dropped off at your work site hop in a cage that is on a regular patrol route and put the character in sneak mode.  Your sneak skill will skyrocket as long as there is at least one guard nearby, once you hit an acceptable sneak level (50 is good, but you can max out your sneak doing this if you want, in just a few days at that) then start picking the lock of your manacles, that should train you up to an acceptable picklock to make good your escape.

You can also skip the exploity sneak training and just do the lockpicking and then try to sneak out normally, that is totally doable too.

[Brotato]

Except you still have to have enough skill with lockpicking in the first place (5% chance per attempt) to unlock your shackles. And there's no guarantee you'll get your lockpicking high enough with just the manacles to escape your cage.

[scriver]

Whenever I have been taken prisoner, if the character didn't have lockpicling skill already, they'd have so within minutes. How fast it rises is almost an exploit by itself.

[Ulfarr]

Except you still have to have enough skill with lockpicking in the first place (5% chance per attempt) to unlock your shackles. And there's no guarantee you'll get your lockpicking high enough with just the manacles to escape your cage.

I once got stuck right in the beginning of a run because my character's cage was too far away from any other slaves and I was (un)lucky enough to unlock my shackles on the first try.

[milo christiansen]

I have a mod to fix that, no more minimum required skill. You need to get that lockpick skill somehow, and there isn't always locks of the right level scattered around.

[Sirus]

I'm genuinely not sure what people are talking about, here. I've never had trouble lockpicking my way out of cages or prisoner poles, even with a brand new character. I did the Enslaved start, and my biggest challenge was figuring out how to get past the gate guards rather than escaping my bonds each night.

[Ulfarr]

You need to have a certain level (depending on which lock) of lockpicking before the game lets you to pick it. If the slavers put you in a somewhat isolated cage then you can't train your lockpicking by unlocking the shackles from other prisoners because you can't reach them while you are in said cage. That leaves you with only your own shackles to train on and if you happen to unlock them on your first tries then your lockpicking will not be raised enough to then unlock the cage.

Granted this is somewhat rare but it can happen. Maybe I was just unlucky but for whatever reason the slavers wouldn't take my character out to work/move in another cage, so I was stuck for 3-4 days inside a cage, before I got bored and started over.

[NullForceOmega]

The solution to that is to throw out your shackles, then the slavers will put a new set on.  At least they always have for me.

[Ulfarr]

I did. They weren't even coming in the same building I was.

[Sirus]

You need to have a certain level (depending on which lock) of lockpicking before the game lets you to pick it. If the slavers put you in a somewhat isolated cage then you can't train your lockpicking by unlocking the shackles from other prisoners because you can't reach them while you are in said cage. That leaves you with only your own shackles to train on and if you happen to unlock them on your first tries then your lockpicking will not be raised enough to then unlock the cage.

Granted this is somewhat rare but it can happen. Maybe I was just unlucky but for whatever reason the slavers wouldn't take my character out to work/move in another cage, so I was stuck for 3-4 days inside a cage, before I got bored and started over.

That's what I'm confused about. Fresh character, locked in a cage, still able to get out of the cage before the first night is out. I didn't even bother with the shackles for some time, I merely got in and out of the cage multiple times.

Something isn't matching up, here. I have found chests that were too complicated for a newbie to successfully pick, but I've never had issues with cages or prisoner poles.

[NullForceOmega]

Since locks are randomized it is possible to get one that is too high to pick, I've had it happen with a prisoner pole specifically.  Very rare but it does sometimes happen.

[Glloyd]

Yeah, some slave camps have noticeably higher lock levels than other ones. It's also just randomized within the camp, so it's totally possible to get stuck in a high level cage and have to get creative to get out.

[milo christiansen]

Speaking of lockpicking: I just started over fresh with the "Slaves" scenario. So far it is lots of deliberately failed escape attempts to get more-or-less safe stealth, thievery, assassination, toughness, lockpick, and dodge training. I'm sure the guards hate me.

I could probably have escaped long ago, but all the training opportunities makes it hard to want to leave...

EDIT: Keep removing your shackles and putting them in your inventory for some easy strength training weights.

[EuchreJack]

You need to have a certain level (depending on which lock) of lockpicking before the game lets you to pick it. If the slavers put you in a somewhat isolated cage then you can't train your lockpicking by unlocking the shackles from other prisoners because you can't reach them while you are in said cage. That leaves you with only your own shackles to train on and if you happen to unlock them on your first tries then your lockpicking will not be raised enough to then unlock the cage.

Granted this is somewhat rare but it can happen. Maybe I was just unlucky but for whatever reason the slavers wouldn't take my character out to work/move in another cage, so I was stuck for 3-4 days inside a cage, before I got bored and started over.

That's what I'm confused about. Fresh character, locked in a cage, still able to get out of the cage before the first night is out. I didn't even bother with the shackles for some time, I merely got in and out of the cage multiple times.

Something isn't matching up, here. I have found chests that were too complicated for a newbie to successfully pick, but I've never had issues with cages or prisoner poles.

I agree.  I've noticed its incredibly easy to escape slavery, because the stupid slavers always send my characters outside of the base to mine/farm something.  Just wait for that, then for the guard to get called away, and hoof it.  It does take patience, but it happens.  Plus, my characters get free training in athletics, laboring/farming, lockpicking, and maybe even stealth (although usually just running when the guards aren't looking is the best option).
...and since we can make money by selling our own people into slavery, its even more fun!

EDIT: Just read the bit about some cages/poles being too high, that kind of sucks.