On 13/12/12 06:26, Stan Hoeppner wrote:
On 12/12/2012 6:05 PM, Tony Nelson wrote:

I think it's in my best interest to get TLS operational again.

So, you encrypt the transmission from the internal corporate groupware
server to the gateway server via a private network that you completely
control.  But then you relay the same message over the public internet
in plain text.


TLS encrypts the whole connection including the authentication - maybe the OP is more concerned about passwords being sent in plain text than the contents of the actual email.

There seems to be a flaw in your logic, in your threat assessment.  Your
stated posture makes it seem you are more worried about malicious packet
sniffing inside your perimeter than outside.


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