For sanity - The Settlers :D

For torture - Championship Manager :sleep

Torture: Xenon 2

Sanity: Pinball Fantasies (would have been another shmup if the Amiga had any good ones).

No you were framed for murder! . Your innocence plea went to trial but the judge screwed you over and planted you in prison with a life sentence.

First week in prison you were on mop duty and late one evening while cleaning the corridors of B block, you saw the warden getting pegged by a female dominatrix in the laundry room.
The warden noticed you looking to which he threw you in the SHU on the very same evening.
Keen not to let his embarrassment pass around the prison its likely you're going to be in there for a long time.. Could be a month or could be for your full sentence. Either-way you find it torture not knowing.

Food isn't great, mostly porridge, they slide it under the door through a small 4 inch high letterbox affair, and the bucket of faeces you live with stinks, but you get used to the smell. You hope soon there will be someone to empty the thing as it's getting quite full.

That is easy one - Civilization

Hours of fun, each game can go different way... Close contenders were X-Com, Colonization, Battle Island / HL, Settler and Elite 1 / 2

Damn, this is a good question. Obviously it has to be a game which you can play for ages and does not bore easily.

the Settlers or Colonization I guess.

X-Com or better yet an AmigaOS port of OpenXCom - https://openxcom.org so I can play hybrid X-Com and TFTD at the same time!

Civilization, as it have great replay value.

Torture: something like Rise of the Robots, and the condition is to be played from floppy drive.

I think I would play Sensible World of Soccer!

Devpac Assembler.

For torture: Either Rick Dangerous or Rainbow Islands Vision factory crack because it crashes on Doh Island

This is rather a faulty premise, isn't it?

Solitary confinement is PUNISHMENT, you're meant to have no entertainment AT ALL.

What you should've done is something along the line of Desert Island Discs instead.

Yeah, because crashing on a desert island and miraclously salvaging a power source, hardware & your favourite content is so much more realistic :)

Gawwwd….:rolleyes

The Amiga was there a long time prior to your arrival and forgotten about.
Its previous owner was a guard at the prison and he was forced to take it to the dump by his wife as he had too many of them at home.
Instead of dumping it he took it to work in hope to play “YOUR GAME HERE” while on duty. But when the warden saw the Amiga he ordered it to be taken home, so the guard secretly stashed it in the SHU instead.
The Guard got fired a few years ago and left it behind.:)

Apidya says hi.

Anyway, my picks:

Game/program: any of the good assemblers will do
Torture: Outrun

I'll take Deluxe Paint III (+manual?) for fun and Gremlins 2 for punishment!