Microsoft Activation "Unable to reach Internet" even though slmgr.vbs gets responses from activation servers

T

teward001

Hello.

We currently are trying to activate a number of Windows Server 2016 systems to power our Remote Desktop Services cluster. The problem we are currently having is that these systems are somehow unable to reach to the Activation servers, and it is unclear why as *no error* messages are being returned by Activation Troubleshooter.

When we use Activation Troubleshooter, it says there is no Internet connection. TCPView from SysInternals shows it reaching out to one of the activation servers (co2.activation-v2.sls.microsoft.com) but that's all we can see, we see it timing out. The servers are BEHIND a Firewall, however there is filtration bypass set up for *.microsoft.com (by regex match) so it should be able to "just go out" without any proxy interception or filtration from behind our XG Firewall.

We DO see an HTTPS error when we try to go to the URL directly about the SSL cert not being valid (probably because it's got multiple CNs and not RFC compliant in whatever way), but it otherwise seems to 'work' getting to the site directly.

Attempting to use slmgr.vbs on the command line to reach to the activation servers DOES get a response about the license key being activated too many times, but we're using a Volume License Key and not an MAK.

Phone / Smartphone activation mechanisms for the activation system do work properly, however, and we DO get the confirmation codes.

However, we can't seem to use Internet based activation, and we currently have an "Allow To Anywhere" rule set up for the subnet.

ALL URLs specified here are bypassed for filtration as well: support.microsoft.com/en-us/help/921471/windows-activation-or-validation-fails-with-error-code-0x8004fe33

Is there some other way to continue to debug this on the remaining systems which still need activated that does NOT require me to do a phone call to activate the servers?

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