WSUS / SUP : System.Net.WebException: The request failed with HTTP status 401: unauthorized.

I noticed recently that after an extended period of being switched off, the Software Update Point in SCCM lab looked extremely poorly. I’m not sure why this was or if it had anything to do with being switched off for several days but in any case here is the scenario:

WSUS lives on a separate server to my site server and SQL is on another separate box (I know, better to install it on the same box as site server but I find few customers these days that’ll let me do this so I keep it this way to replicate their environments as far as possible). Anyway I digress; the setup is as follows:

Comms: HTTPS / SSL throughout  for SCCM and for WSUS.
Version: Current Branch 1606
OS: Server 2012 R2  (WSUS 6.2, commonly referred to as WSUS 4.0)

After noticing some errors in my component status messages with regard to WSUS, I checked the WSUSCtrl.log and saw the following message appearing every minute or so:

System.Net.WebException: The request failed with HTTP status 401: Unauthorized.~~ at Microsoft.UpdateServices.Administration.AdminProxy.CreateUpdateServer(Object[] args)~~ at Microsoft.UpdateServices.Administration.AdminProxy.GetUpdateServer()~~ at Microsoft.SystemsManagementServer.WSUS.WSUSServer.ConnectToWSUSServer(String ServerName, Boolean UseSSL, Int32 PortNumber)
Failures reported during periodic health check by the WSUS Server UT1.BC.LOCAL. Will retry check in 1 minutes

Furthermore, if I ran WSUSUtil checkhealth on the SUP, my Application Log read as follows:

The Reporting Web Service is not working.
 The API Remoting Web Service is not working.
 The Server Synchronization Web Service is not working.
 The Client Web Service is not working.
 The SimpleAuth Web Service is not working.
 The DSS Authentication Web Service is not working.
 On 13/10/2016 19:56:06, component SMS_WSUS_CONTROL_MANAGER on computer UT1.TEST.LOCAL reported: WSUS Control Manager failed to configure proxy settings on WSUS Server "UT1.TEST.LOCAL".

Possible cause: WSUS Server version 3.0 SP2 or above is not installed or cannot be contacted.
 Solution: Verify that the WSUS Server version 3.0 SP2 or greater is installed. Verify that the IIS ports configured in the site are same as those configured on the WSUS IIS website.You can receive failure because proxy is set but proxy name is not specified or proxy server port is invalid.

Not good. Fortunately the fix was straightforward:

I ran c:\Program Files\Update Services\Tools\wsusutil.exe configuressl ut1.test.local
and then I saw URL: https://ut1.test.local:8531 appear on the screen.
Then restarted the IIS services (IISAdmin, WWW) and all sprang to life. An IISReset would probably have done the same thing. After this the log should start to look like that below.

wsuslog

(Open image in a new tab to see more clearly)

Assuming you are configured for SSL and for some reason you see something like URL: http://ut1.test.local:8530 instead, then most likely the SSL settings for WSUS are probably incorrect. Ensure you have the settings below in place in IIS:

1. WSUS Administration. SSL Settings should be unchecked / ignore.
2. ApiRemoting30. SSL settings should be checked / ignore.
3. aspnet_client. SSL settings should be unchecked / ignore.
4. ClientWebService. SSL settings should be checked /ignore
5. Content. SSL settings should be unchecked / ignore.
6. DSSAuthWebService. SSL settings should be checked/ ignore.
7. Inventory. SSL settings should be unchecked / ignore.
8. ReportingWebService. SSL settings should be unchecked / ignore.
9. SelfUpdate. SSL settings should be unchecked / ignore.
10. ServerSyncWebService. SSL settings should be checked / ignore.
11. SimpleAuthWebService. SSL settings should be checked / ignore.

One thought on “WSUS / SUP : System.Net.WebException: The request failed with HTTP status 401: unauthorized.”

  1. Thanks! Didn’t take long to solve this. I think I was running WsusUtil.exe configuressl, but didn’t have the server name after it. Which maybe defaults to netbios name? not sure, but it wasn’t working. Thanks again!

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