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Skype for Business behind a transparent squid (TProxy) HTTP/S

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I have a Ubuntu 16.04 server with Squid 3.5.22 installed. It acts as a gateway in a LAN.

It is configured to intercept HTTP and HTTPS traffic (Transparent). So iptables redirects were used for ports 80 and 443.

The server runs two scripts: 
nat.sh to bridge the two network cards, allowing LAN computers access to the internet through the servers Internet interface card.
iptables.sh which defines the ip rules and port forwarding: http://pastebin.com/SqpbmYQQ


BEFORE RUNNING iptables.sh...

When I connect a LAN computer to it, everything works as expected. Complete Internet access with some HTTP and HTTPS domains blocked/redirected to another page. Skype for Business logs in successfully.


AFTER RUNNING iptables.sh
Skype for Business disconnects, and fails to re-connect, normal skype works just fine.

I revised: https://support.office.com/en-us/article/Create-DNS-records-at-eNomCentral-for-Office-365-a6626053-a9c8-445b-81ee-eeb6672fae77?ui=en-US&rs=en-US&ad=US#bkmk_verify And added all DNS configurations on enom.

That got rid of the DNS error I was getting to another error saying service is temporarily unavailable.

Any suggestions to why this is happening? Any solutions?

Note: both router and Ubuntu's WAN interface use Google's 8.8.8.8 DNS


Any help is really appreciated as I have been trying to fix this for days!





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