Can you connect to the smtp.gmail.com:587 manually from that machine? (for 
example using netcat or telnet)

You mentioned that you use postfix install as your MTA … you can then switch 
monit to use your postfix instead of gmail:

    set mailserver 127.0.0.1

Regards,
Martin


On Feb 3, 2012, at 12:43 AM, Simpson, Matt 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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