Hi All,

In my home we have got an internet connection which is connected to desktop machine having two network cards. One card is connected to external internet and second is used for internal LAN.

We have installed a proxy on desktop machine so that we can connect to internet through proxy. So we are not able to telnet to smtp.gmail.com 587 from laptops of internal LAN laptop installed with ubuntu and fedora.

At the same time we are able to ping smtp.gmail.com from the desktop machine which is exposed to internet.

I want to automate email through shell script using smtp.gmail.com.

Please advice me to overcome this issue.

Is your squid proxy working in a transparent mode? Or you configure browsers for proxy settings?

Thanks for your inputs chaitanya,

I am using freeproxy as proxy to connect to internet. Now I configured freeproxy to forward the incoming smtp traffic to smtp.gmail.com 587.

I followed this guide

Now its working fine..

But this would forward all the smtp traffic to smtp.gmail.com. It would create issues if other smtp traffic is also forwarded to gmail. Have you installed freeproxy on some Linux distribution or is on windows? If you are linux then just MASQUERADE the outgoing connections and you should be able to connect.

Yes I wanted to achieve same.

Yes, definitely this redirects all smtp traffic to smtp.gmail.com

I have installed freeproxy on Windows which is exposed directly to the internet.

Under what circumstances that masquerading outgoing connections of Windows would help me ?

Please Advice

I do not know how to masquerade the connections on windows. In Linux you can easily do that using iptables.