Hi nic,
You might be interested in the proprietary
OpenVPN Connect client, which is made to reconnect when a machine wakes up. It is fully interoperable with open source servers, but it's easiest to use with inline config files. The commercial
Access Server software and
OpenVPN Cloud service do this for you, but it can also be done manually for connecting to open source servers. See the section on "
INLINE FILE SUPPORT" in the
openvpn(8) manual.
regards, rob0