Microsoft SSL issues

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andynzengr

3 posts

Wannabe Geek

#177784 14-Aug-2015 07:02

Hey All,

Been scanning forums with respect to fe2.updates.microsoft.com and the bizarre cert validation issues that you get when hitting this URL. As far as I can gather, this issue has been around since late 2014 and still hasn't been resolved.

Its strange that Windows by default doesn't trust the Root or Intermediate... I can manually trust the Root and Intermediate manually but wondering if its actually legitimate site (appears to be hit when synchronising WSUS). Bizarre that MS haven't pushed out an update so that Windows trusts the Root and Intermediate for this site.

Am I losing the plot or is this an outstanding issue that MS still hasn't resolved?

Any thoughts appreciated.

Cheers,
A

Inphinity

2780 posts

Uber Geek

#1366059 14-Aug-2015 08:20

Are you still trying to get WinXP or earlier updates on WSUS by chance?

andynzengr

3 posts

Wannabe Geek

#1366084 14-Aug-2015 09:16

Absolute legend.

Root cause was Office 2002/XP product was selected. Unselecting that option allows updates to pass through the CheckPoint using HTTPS inspection without needing to put a bypass exception in place for that URL.

Well spotted! I no longer get sync failures due to that URL not being valid which is awesome.

nathan

5695 posts

Uber Geek
Inactive user

#1366113 14-Aug-2015 09:49

andynzengr: Hey All,

Been scanning forums with respect to fe2.updates.microsoft.com and the bizarre cert validation issues that you get when hitting this URL. As far as I can gather, this issue has been around since late 2014 and still hasn't been resolved.

Its strange that Windows by default doesn't trust the Root or Intermediate... I can manually trust the Root and Intermediate manually but wondering if its actually legitimate site (appears to be hit when synchronising WSUS). Bizarre that MS haven't pushed out an update so that Windows trusts the Root and Intermediate for this site.

Am I losing the plot or is this an outstanding issue that MS still hasn't resolved?

Any thoughts appreciated.

Cheers,
A

can you describe what the problem actually is?

What error code are they seeing, logs, etc? Are you behind a proxy that tries to inspect HTTPS traffic? If proxy is acting as MITM while doing that, WU will not trust the connection. We’re extremely particular about SSL cert for security reason.

andynzengr

3 posts

Wannabe Geek

#1366354 14-Aug-2015 13:59

Absolutely,

If you browse to https://fe2.update.microsoft.com, the certificate is invalid.

Root: Microsoft Root Certificate Authority 2011
Serial: 3F 8B C8 B5 FC 9F B2 96 43 B5 69 D6 6C 42 E1 44
Validity: 23 Mar 2036
Common Name: Microsoft Root Certificate Authority 2011

Intermediate: Microsoft Update Secure Server CA 2.1
Serial: 33 00 00 00 0A B8 91 A2 C8 0A 50 A5 DF 00 00 00 00 00 0A
Validity: 22 Jun 2027
Common Name: Microsoft Update Secure Server CA 2.1

Server Certificate: fe2.update.microsoft.com
Serial: 33 00 00 00 4B 71 09 0E 6C 98 35 08 53 00 00 00 00 00 4B
Validity: 17 Mar 2016
Common Name: fe2.update.microsoft.com

I would have expected both the Root and Intermediate to be trusted in the local certificate store on a MS Server 2012 server, tested from Windows 7 PC and Safari. None of these browsers trust the Root or Intermediate.

I inspect SSL on my perimeter CheckPoint firewall, WSUS by default hits fe2.update.microsoft.com for what appears to be for updates referencing Windows XP/Windows 2000. Removing those check boxes in WSUS avoids the server trying to access fe2.update.microsoft.com and traffic is permitted/synchronisation completes. The configuration on the CheckPoint will drop any HTTPS connection that is invalid (including if CRL/OCSP URLs are not reachable). All other HTTPS communication through my firewall, either inspected or bypass work fine. It seems like the server certificate needs to be reissued and that the current certificate being presented to the client is no trusted.

Regards,
A