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I'll try to give a thorough rundown of the environment:

  • anonymous proxy
  • proxy must be set for Internet access
  • 2 Squid proxies on RHEL8 behind an f5 - not caching
  • 2 Windows AD DCs, both running 2019 Standard experiencing the issue. Both freshly installed
  • have the following set in a whitelist (developed this list while watching the Squid access logs):
    • .microsoft.com
    • .windowsupdate.com
    • .live.com
    • .msftconnecttest.com
    • .windows.com
    • .azureedge.net
    • .azure.com
    • .visualstudio.com
  • no WSUS set (double-checked via gpedit)
  • setting the proxy both in IE settings & via netsh
  • double-checked each instance locally to ensure that proxy settings were indeed being set (both via netsh & by checking the IE settings)
  • attempts to update produce a 0x80072EE6 error in the Windows Update Event Viewer logs when attempted locally, and via an Ansible playbook
  • playbook being run via WinRM connection w/NTLM auth using a domain admin acct

I can see successful connections such as the following with each attempt:

04/Aug/2022:15:59:29 -0400    864 10.200.138.253 TCP_TUNNEL/200 6321 CONNECT v10.events.data.microsoft.com:443 - HIER_DIRECT/v10.events.data.microsoft.com -
04/Aug/2022:15:59:47 -0400    353 10.200.138.253 TCP_TUNNEL/200 4060 CONNECT settings-win.data.microsoft.com:443 - HIER_DIRECT/settings-win.data.microsoft.com -

I can also see that other Windows instances on the network are actually downloading updates:

04/Aug/2022:15:36:20 -0400    674 10.200.138.253 TCP_MISS/206 66151 GET http://au.download.windowsupdate.com/d/msdownload/update/software/defu/2022/06/updateplatform_f7e39cbc74e49ac493f62d12e63f1f9df9453af1.exe - HIER_DIRECT/au.download.windowsupdate.com application/octet-stream
04/Aug/2022:15:36:21 -0400     56 10.200.138.253 TCP_MISS/206 918120 GET http://au.download.windowsupdate.com/d/msdownload/update/software/defu/2022/06/updateplatform_f7e39cbc74e49ac493f62d12e63f1f9df9453af1.exe - HIER_DIRECT/au.download.windowsupdate.com application/octet-stream
04/Aug/2022:15:36:21 -0400     23 10.200.138.253 TCP_MISS/206 348408 GET http://au.download.windowsupdate.com/d/msdownload/update/software/defu/2022/06/updateplatform_f7e39cbc74e49ac493f62d12e63f1f9df9453af1.exe - HIER_DIRECT/au.download.windowsupdate.com application/octet-stream

Ansible playbook uses the following plays:

- name: Configure IE to use explicit proxy host with port and without auto detection
  community.windows.win_inet_proxy:
    auto_detect: no
    proxy: "{{ proxy_host }}:{{ proxy_port }}"
    bypass: "{{ proxy_env.no_proxy }}"

- name: Set the proxy to be able to run  Windows Updates
  ansible.windows.win_command: netsh winhttp import proxy source=ie


- name: Install all security, critical, and rollup updates without a scheduled task
  ansible.windows.win_updates:
    category_names: "{{ win_update_categories }}"
      reboot: yes
      reboot_timeout: 3600

Playbook resulting error:

TASK [Install all security, critical, and rollup updates without a scheduled task] **********************************************************************************************************************************************************************************************************
An exception occurred during task execution. To see the full traceback, use -vvv. The error was: at <ScriptBlock>, <No file>: line 753
fatal: [<hostname>]: FAILED! => changed=false 
  failed_update_count: 0
  filtered_updates: {}
  found_update_count: 0
  installed_update_count: 0
  msg: 'Searching for updates: Exception from HRESULT: 0x80072EE6 - Unknown WUA HRESULT 2147954406 (UNKNOWN 80072EE6)'
  reboot_required: false
  updates: {}

Finally, when I go back to check either of the instances again, the Updates UI reports "No updates available," & there's no sign of the error until I try it again.

Would love to know what's going on here.

Travis
  • 123
  • 8

1 Answers1

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Currently working on a similar(ish) issue on Windows Update via Squid proxy. Please check the Windows Update log at C:\Users\Admin\Desktop\WindowsUpdate.log ( generate first with Get-WindowsUpdateLog ) It might give clues to what is happening. There is a special page with squid recommendations for Windows Update: https://wiki.squid-cache.org/SquidFaq/WindowsUpdate

Issue I am facing is a machine trying to pull updates from https://fe3.delivery.mp.microsoft.com which causes issues with the SSL validation. So looking into SSL-Bump and Peek and Splice options for squid.

Marcel
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  • Thanks for the info about the log - helped me to figure out what my issue was: _domain_ policy had been set to a defunct WSUS server. These are domain controllers, so the policy wasn't visible via gpedit. Once I changed the domain policy, and ran a `gpupdate /force`, the servers were able to update normally. – Travis Aug 08 '22 at 16:36