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forbiden email access

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Hi everyone

I want to add a TMG firewall to my network and I have some question about configuring its rules

1) my boss needs to limit client's access to global emails , actually he needs that non of employers can access global email so they have to use company email accounts for sending or receiving emails

2)also he needs that no one can use any proxy for double cross my limits but I found that some of my employees use a windows based software that works with 443 port and SSL protocol , is there any way that I can use to stop using that software?

Thank you all


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