This is not how Windows code signing is supposed to work. Normally you'd get a countersignature from a timestamp server so that the verification process can prove that the certificate was valid at the time of signing. It would appear that Oculus signed their binaries without using a timestamp server, so without a way to verify when signing happened they become invalid as soon as the cert expires.
This problem is deeper than forgetting to update it. It should never have caused a failure in the first place. Just the fact that the device apparently can't function at all without the internet is a problem too.