Niles Mitchell has a variety of Apple devices, including an iPhone with Siri, an iMac and a Vintage Mac 512K. Using a combination of the old Speak program, AppleScript and iCloud Notes, Mitchell was able to send files from his iMac to his Mac 512K via Siri. It's a clever mix of old and new technology that's worth a watch, even just to hear the antiquated sound of a floppy drive working hard to copy files.
You can check out this Siri-mediated conversation in the YouTube video embedded below.