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Exchange Online with Standard Proxy

Hello,

i want to configure an Exchange Online Account in addition to an On-Premise Account to my Outlook 2010.

The UTM is configured as standard proxy with SSO authentication.

Autodiscover doesn`t really work, i always get a certificate error generated by Astaro HTTP Proxy.
In addition, Outlook wants me to re-enter the credentials all the time.

Microsoft Support told me that the error is related to our proxy, regarding to the certificate error.

So i tried to bypass the proxy with an exception for:
^https?://([A-Za-z0-9.-]*\.) outlook\.com/

^https?://([A-Za-z0-9.-]*\.) office365\.com/

with all options checked (just to try it out)
without success, the certificate error still persists

After that i extended my wpad with these entries:
    if (dnsDomainIs(host, ".outlook.com") ||

        dnsDomainIs(host, ".office365.com"))
        return "DIRECT";


and created a firewall rule to enable the traffic to this urls, but with just the same result.

What can i do?


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