I think, We should append this rule not insert, then
/sbin/iptables -A OUTPUT -p tcp -dport 443 -j DROP
another it block all request on 443 port.
Tell me if i am wrong..

> So , in your case the following rules should work:
>
> ### First allow ###
> /sbin/iptables -I OUTPUT -d gmail.com -p tcp --dport 443 -j ACCEPT
> /sbin/iptables -I OUTPUT -d <GTALK IP > -p tcp --dport 443 -j ACCEPT
>
> ### Then Deny ###
> /sbin/iptables -I OUTPUT -p tcp --dport 443 -j DROP
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