Ignoring all social issues, and treating this the same way I treat other children (i.e. Traders), you could use legal/compliance technology. In this case you point the MX records for the domain via a provider such as MessageLabs and then direct the server to send all mail through the same pathway. If rackspace are amenable to sending through an MX relay of your choice this would work pretty well. I am also ignoring cost as if you *have* to meet a legal requirement I will assume that this is the most important consideration.
Once this is done you send Messagelabs a list of users - in your case just one or two humans with any number of email addresses/domains associated with those users (they base pricing on pairs of eyeballs not on mail addresses). You can then setup the adults as "compliance officers" who get cc'ed when any mail contains certain keywords. They are also able to do full text search on any mail sent or received. In addition MessageLabs handles whitelisting of email addresses to control who the child sends to and receives from. There is a quarantine function to trap any blacklisted mail for review. So - a little overengineered - but would only require one time input from a technical friend and would be a fairly robust solution for mail to/from a specific domain. Also, the messagelabs is not an endorsement. I am evaluating them at the moment and they seem to cover all the bases needed for this scenario. There are many others in the space who could do something similar. Thoughts? Rob
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