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Problem with SSL VPN client and O365 in windows 10

Scott_D_L

Hi There,

Putting this here to save someone else some time in the future.     We recently moved our users to a new O365 tenant. In this new tenant we had enabled MFA.   After we did that,  I started having an issue with outlook not working if I restarted outlook up after I had used the Sophos SSL(openvpn) client to connect.  I would have to open outlook first to get Authenticated,  then startup VPN.  I dont have the exact message any more but basically outlook popped up a Can't connect Message(and Please enter your password in lower right of outlook) when I had started the VPN client before starting outlook.

After doing some googling  and looking at other firewall vendors forums who also use a OpenVPN based SSL client, it appears that you have to set the gateway IP under the Sophos SSL Adapter or whatever yours is called under the network adapter listing.  Without doing this, the Sophos adapter's connectivity status will show "unknown" (instead of "Internet Access".  Setting the gateway address under tcp IPv4 properties in the  Sophos adapter remedies that. I just used the gateway address a netstat -rn showed me as the default route.

If I was using split tunneling this would not be an issue(I'm assuming), but I tunnel all traffic through the ssl vpn client.

So I think its a combination of Outlooks / MFA authentication process, windows 10 network location service, and the the openvpn client running in fully tunneled mode.

I hope this helps someone in the future. If anyone else has any other ideas, please chime in.

Thanks,

-Scott



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  • 0

    First of all, thank you for the post. I've been meaning to create one but never got around to it. I have previously logged a ticket with Sophos support which ended with them advising that the issue is with Microsoft/Office 365 given everything else seems to be working.

     

    The following routes are added by the VPN connection which should have achieved the same effect as the below, however Office 365 authentication intermittently doesn't work.

    route.exe ADD 0.0.0.0 MASK 128.0.0.0 10.81.234.5

    route.exe ADD 128.0.0.0 MASK 128.0.0.0 10.81.234.5

    Adding the following route solves the issue with authenticating to Office 365.

    route.exe ADD 0.0.0.0 MASK 0.0.0.0 10.81.234.5

  • 0 in reply to Wimar Aswan

    This works indeed, however it is a workaround and no real solution. Any news on this?

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