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Sneak in, pick the cage, NOT the shackles, pick them up, sneak out to the base of the tower past the gate and around the corner from the entrance gate so you're out of sight, put them down, pick the shackles, leave the area. They should still be yellow arrow when you highlight them, and should still be following you. I had to run from Tengu's Vault to almost the Grey Desert border for them to stop and give the join dialog, but It worked, and I was able to reproduce it.
I haven't tried freeing them and then picking them up after a guard downs them and taking them out of the tower but staying close enough that they can recover and walk again and then proceeding to leave the area, so I cant say if that will work.
Hope this helps someone.
It worked for me. I believe Shidan's right that carrying can break things, but my impression is that it only does so if you carry him too far away before allowing him to recover and resume following.
Shidan is right. I believe that if you leave the area while carrying them it will break it. And that's what most will do. That's how I ended up on this page. When sneaking failed, and they got downed, I grabbed them and ran to the waystation to the south. When they healed enough to leave their recovery coma, they just ran of into the desert. Confused I googled my issue and found this discussion.
I believe the trick is not carrying them out of whatever invisible zone they have to cross to trigger the successful escape event. And that zone's size varies depending on the event. Random slaves only have to walk a little ways. I had to cross half the desert with Espher. I only found this on accident when I fudged stealth attempt #978 and noticed I had the pick up option.