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In The Matrix, the Matrix itself is a simulated version of Earth in the 90's.
Being as we had access to primitive forms of technology that were later used to create Artifial Intelligence and eventually the Matrix itself in that time (such as programming languages and technological hardware), does the Matrix frequently "reset" the level of technology available to the people in it to stop them from ever gaining a technological advantage over the machines that are imprisoning them?
Referring you back to this answer, the thing you need to understand about the world of the matrix is that it's a setup, a scam, a flim-flam. Everything you see inside the Matrix has been 'rebooted' dozens, if not hundreds of times before. The machines appear to have total control of the whole environment including the memories of its inhabitants.
The only people who aren't subject to this memory alteration are those who're disconnected from the Matrix and we learn, later that their entire existence is also a put-up job, a concoction, a hustle, a subterfuge. Zion is periodically destroyed and recreated by the machines to their own specification. This includes the knowledge they're given access to and the technology they're permitted to use.
It's arguable that the reason why Trinity is such a good hacker is that because at the start of each new loop, she's already got knowledge of advanced programming languages but there's no real evidence of this in the film.
They could if it would serve them in some way, but afaik there is no indication its happening that way.
On the contrary, if we accept, that whole matrix and the world presented as "outside" is still another simulation and that the machines are trying to actually get to the point, when coexistence with mankind will be maintainable. It would serve purpose to advance available technology in each iteration of matrix so humans can get used to it.
Perhaps the whole point of matrix in this perspective would be that natural advancement is progressing far to quickly for humans to adapt to new ideas (conflict of new progress vs old habits), and so machines in controlled environment are trying to make humans more open to new ideas at the speed humans can handle.
