Comment by a2128
The technology was certainly there, BonziBuddy existed around the same time and was widely condemned as a spyware and adware ultimately resulting in its demise. Today Microsoft officially does many of the things BonziBuddy used to do and people just see it as normal.
Digital Convergence tried to do similar with the CueCat, a low-cost barcode reader that had a hardware serial number and for which the official software to drive it required you sign up for an account with them, giving them PII. When people figured out how to neuter the serial number and encryption in hardware, DC invoked the DMCA.