When you use a VPN can your OS update request be used to de anonymize you? I would think that Microsoft or Apple would get a request saying "the OS running on t

When you use a VPN can your OS update request be used to de anonymize you? I would think that Microsoft or Apple would get a request saying "the OS running on this machine with activation token 0xfe875c56a788d0 is checking for an OS update" regularly, so that the government could subpoena for the activation token held by the device that had IP 164.21.13.112 at 7pm on March 25, and then for all other IPs that this token has ever requested OS updates from.