Hi Matt,

If I recall reading somewhere there is an issue with Gmail and Monit using
TLS. Use SSL instead:

set mailserver smtp.gmail.com port 465 username "username" password
"password" using sslv3

This is what we use.

Cheers,

Lukasz

On Thu, Feb 2, 2012 at 4:43 PM, Simpson, Matt <[email protected]> wrote:

>  Good afternoon, everyone.****
>
> ** **
>
> I am running a fresh postfix install as my MTA on my local Ubuntu 11.10
> machine, and I’m using Monit.  I set the following parameters in
> /etc/monit/monitrc:****
>
> ** **
>
> set mailserver smtp.gmail.com port 587 username “<my username>” password
> “<my password>” using tlsv1 with timeout 30 seconds****
>
> ** **
>
> however, in monit.log, this is the response:****
>
> ** **
>
> [EST Feb  2 18:38:10] error            : Cannot open a connection to the
> mailserver ‘smtp.gmail.com:587’ – Transport endpoint is not connected****
>
> ** **
>
> Thanks,****
>
> ** **
>
> *Matt Simpson* ****
>
> ** **
>
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