SC2Mapster

sorry, i meant the player group- pick each player in All Players. also i think i7esperado's way of attaching the region to the unit is wayyyyyy better than the one i proposed.

have an array of units the size of the max number of players, and an array of regions the same size. when the probe is first created for a player, set the variable at the player's index to the probe, and set the region variable the same way. this is what your move region trigger might look like:

event: every half a second
actions:
for each player in all players:
  if player controller of picked player === user:
    if probes[ picked player ] != No unit:
      move regions[ picked player ] to position of probes[ picked player ]

have another trigger that like

event: a unit dies
condition: type of trigger unit == probe
actions: 
probes[ owner of unit( triggering unit ) ] = no unit
make jailed probe

and the jail break trigger

event: unit enters region (jailbreak region)
action:
for each player in all players:
  if picked player has probe in jail region:
     destroy that probe
     create a new probe at jail break region
     set probes[ picked player ] to last created unit

sorry for the very sloppy trigger writing, i'm kinda lazy right now and don't have the editor on this computer. i'm sure there's a few mistakes in there but i hope it helps.