Following up the Beware the Transparent Proxy…Your Faith In VPNs Might Waiver post – the problem seems to be that the VPN client in question allowed split tunneling (rarely a good idea). If a split is allowed, not all the traffic goes through the VPN.
OR, maybe the VPN client went into sleeper mode or was deactivated by user error (happens more than anyone likes to admit!). Most people find layers of security irritating and turn them off.
Without access to the actual device, it seems to be a setting issue or Hoff is testing a weak client (NCP’s solves all these issues – even an option to prevent user tampering).