I'm very familiar with that argument, it's almost a trope at this point; however it is completely logically unrelated to the OP's take.
Unless you think hayst4ck was lamenting the plight of the dictators who have it too easy these days and won't learn to properly internalize the fine essence of clearing peaceful protests the old-fashioned way, when it needed riot shields and teargas?
> it is completely logically unrelated to the OP's take
The point is people have been arguing that their era is the last for freedom because after the invention of writing or phalanxes or cannons or blue-water navies or industrial warfare or nuclear weapons or AI and drones the powerful will have all the chips. It's not true, and you'll almost always find a balancing meme around how those same technologies are going to empower anarchists.
Drones, AI and all of the aforementioned technologies make projecting power easier. That says nothing about who holds that power. The same surveillance tools that make identifying protesters easier also make e.g. determining where particular riot police live possible.
Plato's argument wasn't that his era was the last for freedom, it was that writing would spoil people's ability to memorize their oral traditions when they have the comfort of reaching for their notes. And in fact he was probably right about that, and we experience the continuation in the extreme today with the convenience of Wikipedia, and I can hardly find my way downtown when my phone battery dies and I can't check Google Maps.
New technologies do change the world, and society, usually in irreversible ways. In many aspects for the better, but in some aspects for the worse. To argue that because Plato was wrong about writing, therefore the things you value about society will continue as always, is to bury your head in the sand. Freedom, anonymity, and the vulnerability of the few and powerful to the disgruntled many are all things that can disappear with the shifting sands of time and technology. An argument that they will or won't must be grounded on the merits of the particulars.
Athenians were saying this in respect of writing.