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How secure is an anonomous mail-server

Suppose somone wanted to compromise an anonomous mail-server.  Couldn't it
be possible without the owner of the mail-server knowing?  The attack might
consist of monitoring all traffic to and from that address.  Unless the 
server waits a long and random time to forward the incoming mail, couldn't
a mapping be made of real-name/possible-anon-names?  If a users uses the
same anonomous name for long enough (2 times?) couldn't the attacker be
very confident of the mapping?  If the attacker uses the server themselves
creatively, wouldn't the task be even easier?  

This seems like a simple cipher easily broken.

I am new to this, so I appologize if this is a dumb question.

Peter Baumbach
[email protected]