We are already seeing that companies are fine with giving them unlimited retries on getting out.
Imagine we have all the worst people in history in a jail. Machiavellian murders that desire to kill as many as they can. Not only will they kill, they will manipulate as many other people as they can into killing also.
How many of these people can you afford to let out?
Under your premise it seems to be all of them. Under my premise even letting a single one out is a tragedy.
But this doesn't account for the fact that modern incarceration has built-in safeguards and mitigations based on centuries of cases of people talking, bribing or forcing their way out of prison, as well as getting outside assistance in forms ranging from lawyers to raiding parties equipped for demolition works. There are now procedural and technological means to prevent such incidents for happening, applied proportionally to the degree of risk.
Meanwhile, with AI, we're still at the point where everyone is assuming they can just lock the agent in a sandbox and prompt nicely to not poke at it too hard, and things will be fine. There's no multi-layered structural and procedural safeguards, and there's no recognition for the fact that AI operates faster than humans, and that quite likely it'll be smarter at this than average "jailer".
You're right that a (as-of-yet hypothetical) AI has different abilities, but it also has different weaknesses. It's straightforward to accurately log all of its behaviors, and you can even re-run it to see what it would do in myriad situations.
In principle that sounds true, but your specific example was already disproven in practice. Look at the Hugging Face hack - the amount of logs collected is so massive, that no one is even approaching this without using LLMs to help sift through them. With current models we're already way past being able to keep up with the volume of behavioral logs, and that's for post-hoc analysis; for real time defense, we already rely on classifiers (read: weaker LLMs and different ML models) to do this job.
This will happen earlier than AGI.
There's so many angles to go at it too, beyond bribery and threats - humans can be tricked, nerd-sniped / baited by exploiting their curiosity or worries, overwhelmed with information or raw sensory input, etc. Depending on whether there's more than one operator involved, the trick may involve playing one human against another, etc.
Hell, humans get tired; I wouldn't be surprised if an effective breakout happened just because agent output something that, at first glance, looked like system-level message that makes the operator do the wrong thing in panic, or from muscle memory. Simple thing like:
$ sudo journalctl ...
password: