Sending email over SMTP with STARTTLS (sending email via gmail)

Bob Sneidar bobsneidar at
Wed Apr 27 17:34:45 CEST 2016

But if the encryption is not enabled at the source, it is still locally sniffable, and therefore non-HIIPA compliant, not to mention any government or contractor regulations that may apply.

Bob S

On Apr 27, 2016, at 08:22 , Mike Kerner <MikeKerner at<mailto:MikeKerner at>> wrote:

We have a similar setup.  We get around this another way, namely by routing
smtp connections through a local ISP, which gets rid of the need to do all
the direct-to-google connections.

On Wed, Apr 27, 2016 at 11:06 AM, Bob Sneidar <bobsneidar at<mailto:bobsneidar at>>

This comes up from time to time. I've attempted this with no success. SSL
and TLS are fairly involved, and would require some kind of plug-in to be
written which was capable of interacting with the security elements of
modern OSes. I tried shelling this out, but the Windows CMD shell,
specifically the telnet client, has no access to TLS libraries so far as I

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