Thanks for that BAlfson. Unfortunately and as I mentioned in my post, I have already tried all of the time-adjusting bits. Although not mentioned in the post, I had also already done the re-registering of those DLL files as well.
However I do have news to report... I did get a little further through some research done independently.
The problem seems to be that the Astaro is proxying
all SSL traffic. Not just traffic from the user session. What this means is this:
When you use MS Update, much of the traffic is secured and signed. We don't get to see this, it is handled by the MS Update DLLs. These DLLs are operating under the system account on the computer, they are therefore independent from the User account. When the user imports the Astaro's Webadmin Proxy CA certificate to the Trusted Root Certification Authorities container, it only applies to his user account and not to the whole computer.
This means that when the Update software attempts to authenticate the Microsoft update files, it fails because all it sees is a Certificate signed by the Astaro's Proxy CA. That CA is only recognised under the user account and not under the machine's system account, and so the authentication fails and we get the standard Microsoft certification error which incorrectly burbles-on about time synchronisation issues.
What needs to happen is the Astaro's Proxy CA certificate, needs to be installed to the machine's Trusted Root Authority container. To do this you need to import the Astaro's Proxy CA Certificate using the the Microsoft Management Console (MMC).
The steps are these...
1.) Firstly save a PKCS#12 copy of the Astaro's Proxy CA certificate somehere on an accessible drive.
2.) Open the Microsoft Management Console by typing "MMC" in the run box (Start>Run>"MMC")
3.) Add the certificates Snap-in by selecting FILE>ADD/REMOVE SNAP-IN...
4.) Hit the Add button and select certificates from the list
5.) Select the "Computer Account" radio button
6.) Click Finish and close the list of snap-ins
7.) Click OK to add the certificates snap-in, which should now be visible in the Add/Remove Snap-ins window
8.) Expand the list of certificate containers, right click "Trusted Root Authorities" and choose "Import"
9.) Now brows to the PKCS#12 file you exported from the Astaro earlier and select it, (you may need to mess with the file types at this point)
10.) A message pops up saying the import was successful
You are done.
This for me took away the cert time issue but brought up another error, which I'll detail in my next post once I've kicked it for a bit...
Windows Update fails due to Cert. time error (ASG HTTPS Proxy problem?)
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