The more high tech one makes security, or anything else, the easier it is to break the system. The organization becomes reliant on the high tech security devices and they forget how to carry out simpler tasks.
As an example, a system tracks each prisoner as he moves anywhere throughout the prison. You break that system and the guards forget that you can assign guards to watch the weak points, then order all prisoners to their cells and visibly inspect to see that they are actually there.
I was going to make this point. It is mostly correct.
The more high tech security is, the easier it is to break the system IF YOU KNOW THE SYSTEM.
In a high tech society, guards will become incredibly complacent. In fact, the vast majority of the security will be automated. Thus, its simply a matter of getting people with the right skill set, knowledge, and equipment to hack into the system.
THe best advice I would give you is to first develop your prison and security measures. THEN figure out how to break your prisoners out.
For a futuristic high tech society and it's maximum security prison, here are a few things i'd have.
Suicide Collars: Prisoners are required to wear electronic dog collars that if they pass a certain point, feel excruciating pain and if pass the threshold of the facility die via lethal injection, electrocution, or explosion. Similarly, collars can only be removed by the head of the medical portion of the prisoner (or some suitable authority figure)
Embedded Tracking Device: Every prisoner would have a microchip transmitter embedded somewhere in their body. To add conflict, i'd embed it in their brains!!!
Ultraviolet tatoos: Every prisoner would have tatoos done in a special ink that lights up when a black light is shined on it, this ink is permanent.
Hypnotherapy: Every prisoner would be given subliminal commands to experience extreme pain and distress when contemplating escape.
Laser grids: Various fences and laser grids encompass the prison blocking all avenues of escape and must be deactivated by guards.
Robots: Tireless robots patrol the prisons and its outskirts.
Security cameras: Cameras are everywhere and record everything.
Computer network: All automated security controlled via this network.
That's off the top of my head.
So once you have an idea of the prison THEN you can plan the break out. The more impossible you can make it, the better the conflict. But at the same time, the more 'clever' you can be in terms of the breakout, the more reward for the reader.
And you get bonus points if you can come up with a new spin/angle that has never been done before.
Also, one of the funniest things you can do is to use 'low tech' to defeat high tech. For instance, one of the oldest known methods of the prison break is digging a tunnel.
So you could throw the reader a curve ball, have your characters planning this super duper elaborate high tech break out, and then it sorta gets foiled and just when it looks like they won't be able to do the break out or the plan is just too hard, they go the 'low tech' route. Or perhaps a high tech version of the low tech route.
Here is an idea that just occurred to me.
Lets say the prison has these incredibly powerful plasma conduits that generate gigawatts of plasma/electricty. These conduits are just big enough for someone to crawl through.
Then the prisoners, simply wrap themselves in insulated material and crawl through the conduits. The EM field of the conduits can 'short out' the embedded tracking devices and suicide collars.
Of course, that idea will need some tweaking but I leave that to you.l
Anyways, that's what I got. Good luck
Mel...