Yes, this comes up, but the Court tends to say things that didn’t exist are covered by constitutional rights. I can’t imagine think of any time they asked “could the founders have imagined this?” Television, radio, and the internet are all protected by freedom of the press without anybody ever showing that the founders could have imagined them.
From Heller v. DC:
“Some have made the argument, bordering on the frivolous, that only those arms in existence in the 18th century are protected by the Second Amendment. We do not interpret constitutional rights that way. Just as the First Amendment protects modern forms of communications, e.g., Reno v. American Civil Liberties Union, and the Fourth Amendment applies to modern forms of search, e.g., Kyllo v. United States, the Second Amendment extends, prima facie, to all instruments that constitute bearable arms, even those that were not in existence at the time of the founding.”
A few years after that ruling, the Massachusetts state supreme court upheld a conviction for a woman who had carried a taser for self defense. The Supreme Court accepted her challenge, allowed it to go forward without paying court costs, and unanimously overturned that ruling without asking for oral arguments ( https://supreme.justia.com/cases/federal/us/577/411/ ):
“The court offered three explanations to support its holding that the Second Amendment does not extend to stun guns. First, the court explained that stun guns are not protected because they ‘were not in common use at the time of the Second Amendment’s enactment.’ This is inconsistent with Heller’s clear statement that the Second Amendment ‘extends . . . to . . . arms . . . that were not in existence at the time of the founding.’
“The court next asked whether stun guns are ‘dangerous per se at common law and unusual,’ in an attempt to apply one ‘important limitation on the right to keep and carry arms.’ ... In so doing, the court concluded that stun guns are ‘unusual’ because they are ‘a thoroughly modern invention.’ By equating ‘unusual’ with ‘in common use at the time of the Second Amendment’s enactment,’ the court’s second explanation is the same as the first; it is inconsistent with Heller for the same reason.
“Finally, the court used ‘a contemporary lens’ and found ‘nothing in the record to suggest that [stun guns] are readily adaptable to use in the military.’ But Heller rejected the proposition ‘that only those weapons useful in warfare are protected.’
“For these three reasons, the explanation the Massachusetts court offered for upholding the law contradicts this Court’s precedent.”
The fact that Caetano was a unanimous and thorough ruling says a lot to me. Perhaps you’re holding out hope that Heller will be overturned soon, but the chances for that are very slim ( https://youtu.be/nFTRwD85AQ4 ).