Kinda sounds like E&E 101 for the folks that have had SERE.

Having said that, one would have to be ready for a very violent confrontation to escape at arrest. Given that, it is either get gone just before they get there, which means some form of good intel, or effect an ambush and eliminate the adversary on grounds of your choosing.

Either way, a very iff'y proposition, given the setting and historical context.

In transit, really isn't much better as you lack control over your surroundings and are probably under the tightest control as your captors know this is the best time for escape.

Once at your destination, one will have to get a feel for the routine and see when it can be exploited.

Above all are three items of interest.
1) be ready to go instantly should the chance arise out of the blue.
2) understand that you may only have the skin on your back to take with you.
3) what reprisals will be inflicted on anyone you leave behind.
IF IN THE MILITARY
All of the above assumes you have the blessings of the senior prisoner.
but then you know that.