Skype + SSL Interception + Squid in Non Transparent mode

[do1984]

Hello guys.
I'm struggling for a few days about this setup. We have pfsense 2.4.4, using SSL Interception and Squid in Non transparent mode (user auth). Skype used to work in the past, but sometime ago We had a problem with our pfsense install and the backup.xml was old, so we had to build the some "rules" again. Since Skype can't be used through proxy anymore (8+ versions) we have to make it pass Squid, so I'd have to whitelist all the addresses it uses to connect. I captured the addressses through the "Real time" menu and whitelisted all addresses. No luck doing that. Direct outgoing to 443 is blocked, and must remain that way (no direct connection allowed, with exceptions).
Since I'm not using transparent mode I can't just point the Skype addresses to bypass proxy.
I have captured through tcpdump a list of addresses the workstation tries to connect and created Lan rules allowing all those networks to pass(an alias). But none of that worked and users still can't send messages. Sometimes the warning saying "Finish your Wi-Fi setup" don't show, but users still can't send / receive any messages.
My Squid Whitelist now:
client-s.gateway.messenger.live.com
go.trouter.skype.com
api.asm.skype.com
config.edge.skype.com
api.cc.skype.com
login.live.com
consumer.entitlement.skype.com
msftconnecttest.com
www.msftconnecttest.com
onecs-live.azureedge.net
wsapi.skype.com
browser.pipe.aria.microsoft.com
mobile.pipe.aria.microsoft.com
avatar.skype.com
edge.skype.com
people.skype.com
prod.registrar.skype.com
trouter-eus2-b.trouter.skype.com
api.aps.skype.com
msgsearch.skype.com
bn2-client-s.gateway.messenger.live.com
options.skype.com
api.mcr.skype.com
static.asm.skype.com
wdcp.microsoft.com
wdcpalt.microsoft.com
login.skype.com
skype.com
go.microsoft.com
activation.sls.microsoft.com
activation-v2.sls.microsoft.com
validation.sls.microsoft.com
validation-v2.sls.microsoft.com
displaycatalog.mp.microsoft.com
licensing.mp.microsoft.com
purchase.mp.microsoft.com
displaycatalog.md.mp.microsoft.com
licensing.md.mp.microsoft.com
purchase.md.mp.microsoft.com
.microsoft.com
livecmseastus.cloudapp.net
.cloudapp.net
.msn.com.akadns.net
.aria.akadns.net
.s-msedge.net

Does anyone have a tip to make Skype work in this setup? Thanks!

[matyi.szabolcs]

Hi @do1984 !

Thanks for putting the list together. Works great for me!

if you might need a whatsapp list:

# whatsapp
.whatsapp.com
.whatsapp.net
web.whatsapp.com
whatsapp.com
c.whatsapp.net
whatsapp

Regards