What happens when a software bot goes on a darknet shopping spree? (opens in new tab)

In the US, I suspect a prosecutor would successfully gain a conviction against the bot's operator. This verdict would be repeated several times over a dozen years before any judge or jury ever tried to see it another way. And, IMHO, the only other way this could possibly result in anything other than trouble for the operator is if these bots were not only self-replicating, but also self-funding. They'd have to earn funds, open bank accounts, start VPS accounts, etc, and bombard lots of innocent people with illicit goods before any court would entertain the idea that no human was responsible.

I find the legal culpability of this fascinating.

Right now it is an extremely concrete example, and really easy to say that the originator of the bot is at blame and should be prosecuted for buying illegal items.

But, how advanced does a bot have to be before it itself is at blame? What if they'd programmed it to reach out and purchase from any vendor it could find? What if it wasn't programmed to do anything but made random acts, took feedback and then learned from it?

I doubt there's any serious risk of criminal liability here. The key for most crimes is showing (human) intent (by the coders, the operators, or someone). The intent to purchase random items for art via some automated process isn't the same as the intent to purchase drugs for personal use.

That said, if you decide to keep any drugs you get from the not rather than immediately disposing of them, you've demonstrated the requisite intent to be guilty of possession, so there's that.