It occured to me that my real introduction to technological horror and its various sub-branches (like digital horror) was The Simpsons' Treehouse of Horror episodes.
For some people The Amazing Digital Circus was the first time they saw someone play with the "digital format" and digital possibilities when it came to animation in such an intriguing way... But I had already some existential digital dread trown at me with Homer3. "Send in the clones" was my discovery of the whole "mass cloning" horror. My first introduction to a full story about a technological uprising was "Life's A Glitch then You Die", long before I even heard of Maximum Overdrive or discovered at random "Westworld" one night on TV. And of course there's "House of Wacks", a segment which I saw without any knowledge of "2001: Space Odyssey" and which for me will forever remain THE reference basis for a "technological house turning against the owner". When I saw that one male-Alexa-connected-house thing in "Surreal Estate", I immediately knew where it was going thanks to this segment.
[EDIT: Wait... I had forgotten about "Mickey's Mechanical House" - that might be my oldest perception of the "robot house going bad". Oh, and I just remembered that one VERY creepy Space Goofs episode... Damn, the fear of connected houses was actually everywhere when I was young, huh?]
Yes, when I think about it the Simpsons' Halloween specials were my introduction to technological horror. Obviously LONG before I allowed Black Mirror to put existential dread and obsessive paranoia in me, but also before I even started watching Twilight Zone... Outside of this... Well I did caught X-Files' "Ghost in the Machine" (which I somehow remembered as the "murderous elevator episode". And of course "Time Bandits" was my actual childhood introduction to bio-technological horror. H.R. Giger? Get out of here! For me it was always Terry Gilliam. His vintage-technological nightmares haunted me, from "Time Bandits" to "Brazil". I never had "cyberpunk" as a kid (outside of maybe me watching several times "The Fifth Element"), but I had "vintage-technological dystopia breaking down into pieces throughout a Kafkaesque comedy". Which ended up actually making me more receptive to works such as 1984, "We Happy Few", Jean-Pierre Jeunet's dark movies, and by extension of course the Little Nightmares games.
But outside of it... There was Martin Mystery, yes, but it wasn't "really" technological horror. Either it was alien horror (They Lurk Beneath, Summer Camp Nightmare, They Came from Outer Space), either it was mad science horror (The Return of the Beasts, Attack of the Mothman, The Sewer Thing, Web of the Spider-Creature), but never about technology itself - and when it was, it was somehow always about an evil supernatural entity trapped in a virtual dimension (The Mystery of Teen Town, Rise of the Secret Society), a bit like how Stephen King or J-Horror did (The Mangler, Christine, Ju-on, Ringu) and how Creepypastas would later do. I guess they kept the technological aspects more for the other shows they made, like Totally Spies or Team Galaxy... [Edit: Oh and of course these "virtual horrors" are all from season 3, whose one of main goals was to "talk to the new kids" and be more "up to date"]
The Simpsons' Treehouse of Horrors seems to have been a "core" for me... At least until Doctor Who came in and truly settled me in the genre. I mean come on. The Cybermen, the angel-robots (the Host?), the Clockwork Droids, that one television sucking faces, the Lodger episode, that one episode where they get time-bound in the Tardis forced to wait forever, and of course the freakin' Library. OH THE LIBRARY.
And it is quite interesting to see that, in my youth (well, childhood and teenagehood, you know, time is an invention you can stretch how you want) all of this technological dread was counter-balance by a huge wave of "robot are your friends" content that basically present AIs and robots as humans but made with metal instead of flesh... You know, from Robotboy to My Life as a Teenage Robot, from Astro Boy to Absolute Boyfriend...
And sometimes you came onto pure sci-fi products that balanced both "friendly robots" and "ROBOTS ARE ALL GOING TO KILL YOU". Like Ulysses 31
EDIT: OH BY THE GODS AND GODDESSES, how could I forget? Code Lyoko! It was ALSO the main source of technological, virtual, robotic and digital horror back when I was a wee' thing X) Oh damn, Code Lyoko... The show that traumatized and engaged an entire generation of French youths.