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

[Mike Kerner]

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 iotecdigital.com>
wrote:

> 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
> know.
>
> There is a neat little utility called SMTPConsole for Windows where the
> author has built an app which is nothing more than a TELNET shell with
> SSL/TLS libraries built in. I use it to test SMTP connections in the field.
> It may be possible to contact that person and see if you can get access
> to/purchase his libraries and incorporate them into an SSL/TLS library for
> LC.
>
> The best workaround for this is to use a local open relay running on a
> windows server (windows clients do not have this feature built in but there
> are 3rd party offerings which can do this). The relay is then responsible
> for encrypting the traffic. The bugaboo about this method is that anyone
> sniffing the local traffic can see everything being transmitted, so this is
> not a good solution for a HIIPA site, for example.
>
> Bob S
>
>
> > On Apr 15, 2016, at 04:17 , Ben Rubinstein <benr_mc at cogapp.com> wrote:
> >
> > I have a venerable app which does some automated work on a schedule, and
> emails a report.
> >
> > The app uses Shao Sean's libSmtp, dating back to 2005. It's typically
> set up using an organisation's internal SMTP server to send email.
> >
> > Now my client has switched to using Google Apps for business, and asked
> me to switch the app to using a gmail account they've set up for the
> purpose to send emails.  Entering the credentials they provided fails with
> a nessage inb the log "530 5.7.0 Must issue a STARTTLS command first".
> >
> > Evidently this is all part of the shift to encrypting all communications
> (so it's the FBI's fault!).  I don't think libSMTP handles this bit of the
> protocol - and I don't know whether it even can be done through LiveCode,
> since my understanding is that this requires SSL/TLS support.
> >
> > Is it possible to send email over SMTP with TLS using LiveCode?
> >
> > Has anyone managed to send emails by SMTP to gmail server?
> >
> > Many thanks,
> >
> > Ben
> >
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