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Broken update server

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Hello and thank you in advance for assisting me. I apologize if my responses are too verbose. I would rather supply too much information rather than not enough.

Firstly, I am new to the server environment, so please be patient with me. I just started working for this company and have A LOT to learn.

Backstory: I inherited this problem when I started this job, so my knowledge of when this problem first appeared is limited. This seems to be an issue that has been occurring for quite some time. None of the clients are up to date, according to the reports in Update Services. This is a Server 2008R2 box. This machine hosts Sharepoint, SQL databases, as well as the WSUS service. IIS 7 is installed.

Problem: The server appears to be downloading updates from Microsoft without issue. However, all clients fail to pull updates from this WSUS server. They can, however, pull updates from Microsoft. The error code in question is: 80072F8F.

Things I've tried so far: I've checked date and time to ensure they are synced - no apparent issue there. Also, I ran the server clean up wizard in Update Services because I noticed that the server was getting low on disk space. After the cleanup, 82GB are now free.

Below is a portion of the WindowsUpdate.log from one of my clients:

2015-11-24    11:33:39:645    1004    11c0    AU    #############
2015-11-24    11:33:39:645    1004    11c0    AU    ## START ##  AU: Search for updates
2015-11-24    11:33:39:645    1004    11c0    AU    #########
2015-11-24    11:33:39:645    1004    11c0    AU    <<## SUBMITTED ## AU: Search for updates [CallId = {41482C00-1FF6-4B66-9F31-560B9F8C9877}]
2015-11-24    11:33:39:645    1004    eec    Agent    *************
2015-11-24    11:33:39:645    1004    eec    Agent    ** START **  Agent: Finding updates [CallerId = AutomaticUpdates]
2015-11-24    11:33:39:645    1004    eec    Agent    *********
2015-11-24    11:33:39:645    1004    eec    Agent      * Online = Yes; Ignore download priority = No
2015-11-24    11:33:39:645    1004    eec    Agent      * Criteria = "IsInstalled=0 and DeploymentAction='Installation' or IsPresent=1 and DeploymentAction='Uninstallation' or IsInstalled=1 and DeploymentAction='Installation' and RebootRequired=1 or IsInstalled=0 and DeploymentAction='Uninstallation' and RebootRequired=1"
2015-11-24    11:33:39:645    1004    eec    Agent      * ServiceID = {3DA21691-E39D-4DA6-8A4B-B43877BCB1B7} Managed
2015-11-24    11:33:39:645    1004    eec    Agent      * Search Scope = {Machine}
2015-11-24    11:33:39:645    1004    eec    Setup    Checking for agent SelfUpdate
2015-11-24    11:33:39:645    1004    eec    Setup    Client version: Core: 7.6.7601.19046  Aux: 7.6.7601.19046
2015-11-24    11:33:39:660    1004    eec    Misc    WARNING: Send failed with hr = 80072f8f.
2015-11-24    11:33:39:660    1004    eec    Misc    WARNING: SendRequest failed with hr = 80072f8f. Proxy List used: <(null)> Bypass List used : <(null)> Auth Schemes used : <>
2015-11-24    11:33:39:660    1004    eec    Misc    WARNING: WinHttp: SendRequestUsingProxy failed for <https://ITSERV1.semo.health:8531/selfupdate/wuident.cab>. error 0x80072f8f
2015-11-24    11:33:39:660    1004    eec    Misc    WARNING: WinHttp: SendRequestToServerForFileInformation MakeRequest failed. error 0x80072f8f
2015-11-24    11:33:39:660    1004    eec    Misc    WARNING: WinHttp: SendRequestToServerForFileInformation failed with 0x80072f8f
2015-11-24    11:33:39:660    1004    eec    Misc    WARNING: WinHttp: ShouldFileBeDownloaded failed with 0x80072f8f
2015-11-24    11:33:39:660    1004    eec    Misc    WARNING: Library download error. Error 0x80072f8f. Will retry. Retry Counter:0
2015-11-24    11:33:39:691    1004    eec    Misc    WARNING: Send failed with hr = 80072f8f.
2015-11-24    11:33:39:691    1004    eec    Misc    WARNING: SendRequest failed with hr = 80072f8f. Proxy List used: <(null)> Bypass List used : <(null)> Auth Schemes used : <>
2015-11-24    11:33:39:691    1004    eec    Misc    WARNING: WinHttp: SendRequestUsingProxy failed for <https://ITSERV1.semo.health:8531/selfupdate/wuident.cab>. error 0x80072f8f
2015-11-24    11:33:39:691    1004    eec    Misc    WARNING: WinHttp: SendRequestToServerForFileInformation MakeRequest failed. error 0x80072f8f
2015-11-24    11:33:39:691    1004    eec    Misc    WARNING: WinHttp: SendRequestToServerForFileInformation failed with 0x80072f8f
2015-11-24    11:33:39:691    1004    eec    Misc    WARNING: WinHttp: ShouldFileBeDownloaded failed with 0x80072f8f
2015-11-24    11:33:39:691    1004    eec    Misc    WARNING: Library download error. Error 0x80072f8f. Will retry. Retry Counter:1
2015-11-24    11:33:39:707    1004    eec    Misc    WARNING: Send failed with hr = 80072f8f.
2015-11-24    11:33:39:707    1004    eec    Misc    WARNING: SendRequest failed with hr = 80072f8f. Proxy List used: <(null)> Bypass List used : <(null)> Auth Schemes used : <>
2015-11-24    11:33:39:707    1004    eec    Misc    WARNING: WinHttp: SendRequestUsingProxy failed for <https://ITSERV1.semo.health:8531/selfupdate/wuident.cab>. error 0x80072f8f
2015-11-24    11:33:39:707    1004    eec    Misc    WARNING: WinHttp: SendRequestToServerForFileInformation MakeRequest failed. error 0x80072f8f
2015-11-24    11:33:39:707    1004    eec    Misc    WARNING: WinHttp: SendRequestToServerForFileInformation failed with 0x80072f8f
2015-11-24    11:33:39:707    1004    eec    Misc    WARNING: WinHttp: ShouldFileBeDownloaded failed with 0x80072f8f
2015-11-24    11:33:39:707    1004    eec    Misc    WARNING: Library download error. Error 0x80072f8f. Will retry. Retry Counter:2
2015-11-24    11:33:39:723    1004    eec    Misc    WARNING: Send failed with hr = 80072f8f.
2015-11-24    11:33:39:723    1004    eec    Misc    WARNING: SendRequest failed with hr = 80072f8f. Proxy List used: <(null)> Bypass List used : <(null)> Auth Schemes used : <>
2015-11-24    11:33:39:723    1004    eec    Misc    WARNING: WinHttp: SendRequestUsingProxy failed for <https://ITSERV1.semo.health:8531/selfupdate/wuident.cab>. error 0x80072f8f
2015-11-24    11:33:39:723    1004    eec    Misc    WARNING: WinHttp: SendRequestToServerForFileInformation MakeRequest failed. error 0x80072f8f
2015-11-24    11:33:39:723    1004    eec    Misc    WARNING: WinHttp: SendRequestToServerForFileInformation failed with 0x80072f8f
2015-11-24    11:33:39:723    1004    eec    Misc    WARNING: WinHttp: ShouldFileBeDownloaded failed with 0x80072f8f
2015-11-24    11:33:39:723    1004    eec    Misc    WARNING: DownloadFileInternal failed for https://ITSERV1.semo.health:8531/selfupdate/wuident.cab: error 0x80072f8f
2015-11-24    11:33:39:723    1004    eec    Setup    FATAL: DownloadCab failed, err = 0x80072F8F
2015-11-24    11:33:39:723    1004    eec    Setup    WARNING: SelfUpdate check failed to download package information, error = 0x80072F8F
2015-11-24    11:33:39:723    1004    eec    Setup    FATAL: SelfUpdate check failed, err = 0x80072F8F
2015-11-24    11:33:39:723    1004    eec    Misc    Registering binary: C:\Windows\system32\regsvr32.exe  /s "C:\Windows\system32\wintrust.dll"
2015-11-24    11:33:39:941    1004    eec    Setup    Checking for agent SelfUpdate
2015-11-24    11:33:39:941    1004    eec    Setup    Client version: Core: 7.6.7601.19046  Aux: 7.6.7601.19046
2015-11-24    11:33:39:957    1004    eec    Misc    WARNING: Send failed with hr = 80072f8f.
2015-11-24    11:33:39:957    1004    eec    Misc    WARNING: SendRequest failed with hr = 80072f8f. Proxy List used: <(null)> Bypass List used : <(null)> Auth Schemes used : <>
2015-11-24    11:33:39:957    1004    eec    Misc    WARNING: WinHttp: SendRequestUsingProxy failed for <https://ITSERV1.semo.health:8531/selfupdate/wuident.cab>. error 0x80072f8f
2015-11-24    11:33:39:957    1004    eec    Misc    WARNING: WinHttp: SendRequestToServerForFileInformation MakeRequest failed. error 0x80072f8f
2015-11-24    11:33:39:957    1004    eec    Misc    WARNING: WinHttp: SendRequestToServerForFileInformation failed with 0x80072f8f
2015-11-24    11:33:39:957    1004    eec    Misc    WARNING: WinHttp: ShouldFileBeDownloaded failed with 0x80072f8f
2015-11-24    11:33:39:957    1004    eec    Misc    WARNING: Library download error. Error 0x80072f8f. Will retry. Retry Counter:0
2015-11-24    11:33:39:972    1004    eec    Misc    WARNING: Send failed with hr = 80072f8f.
2015-11-24    11:33:39:972    1004    eec    Misc    WARNING: SendRequest failed with hr = 80072f8f. Proxy List used: <(null)> Bypass List used : <(null)> Auth Schemes used : <>
2015-11-24    11:33:39:972    1004    eec    Misc    WARNING: WinHttp: SendRequestUsingProxy failed for <https://ITSERV1.semo.health:8531/selfupdate/wuident.cab>. error 0x80072f8f
2015-11-24    11:33:39:972    1004    eec    Misc    WARNING: WinHttp: SendRequestToServerForFileInformation MakeRequest failed. error 0x80072f8f
2015-11-24    11:33:39:972    1004    eec    Misc    WARNING: WinHttp: SendRequestToServerForFileInformation failed with 0x80072f8f
2015-11-24    11:33:39:972    1004    eec    Misc    WARNING: WinHttp: ShouldFileBeDownloaded failed with 0x80072f8f
2015-11-24    11:33:39:972    1004    eec    Misc    WARNING: Library download error. Error 0x80072f8f. Will retry. Retry Counter:1
2015-11-24    11:33:39:988    1004    eec    Misc    WARNING: Send failed with hr = 80072f8f.
2015-11-24    11:33:39:988    1004    eec    Misc    WARNING: SendRequest failed with hr = 80072f8f. Proxy List used: <(null)> Bypass List used : <(null)> Auth Schemes used : <>
2015-11-24    11:33:39:988    1004    eec    Misc    WARNING: WinHttp: SendRequestUsingProxy failed for <https://ITSERV1.semo.health:8531/selfupdate/wuident.cab>. error 0x80072f8f
2015-11-24    11:33:39:988    1004    eec    Misc    WARNING: WinHttp: SendRequestToServerForFileInformation MakeRequest failed. error 0x80072f8f
2015-11-24    11:33:39:988    1004    eec    Misc    WARNING: WinHttp: SendRequestToServerForFileInformation failed with 0x80072f8f
2015-11-24    11:33:39:988    1004    eec    Misc    WARNING: WinHttp: ShouldFileBeDownloaded failed with 0x80072f8f
2015-11-24    11:33:39:988    1004    eec    Misc    WARNING: Library download error. Error 0x80072f8f. Will retry. Retry Counter:2
2015-11-24    11:33:40:019    1004    eec    Misc    WARNING: Send failed with hr = 80072f8f.
2015-11-24    11:33:40:019    1004    eec    Misc    WARNING: SendRequest failed with hr = 80072f8f. Proxy List used: <(null)> Bypass List used : <(null)> Auth Schemes used : <>
2015-11-24    11:33:40:019    1004    eec    Misc    WARNING: WinHttp: SendRequestUsingProxy failed for <https://ITSERV1.semo.health:8531/selfupdate/wuident.cab>. error 0x80072f8f
2015-11-24    11:33:40:019    1004    eec    Misc    WARNING: WinHttp: SendRequestToServerForFileInformation MakeRequest failed. error 0x80072f8f
2015-11-24    11:33:40:019    1004    eec    Misc    WARNING: WinHttp: SendRequestToServerForFileInformation failed with 0x80072f8f
2015-11-24    11:33:40:019    1004    eec    Misc    WARNING: WinHttp: ShouldFileBeDownloaded failed with 0x80072f8f
2015-11-24    11:33:40:019    1004    eec    Misc    WARNING: DownloadFileInternal failed for https://ITSERV1.semo.health:8531/selfupdate/wuident.cab: error 0x80072f8f
2015-11-24    11:33:40:019    1004    eec    Setup    FATAL: DownloadCab failed, err = 0x80072F8F
2015-11-24    11:33:40:019    1004    eec    Setup    WARNING: SelfUpdate check failed to download package information, error = 0x80072F8F
2015-11-24    11:33:40:019    1004    eec    Setup    FATAL: SelfUpdate check failed, err = 0x80072F8F
2015-11-24    11:33:40:019    1004    eec    Agent      * WARNING: Skipping scan, self-update check returned 0x80072F8F
2015-11-24    11:33:40:019    1004    eec    Agent      * WARNING: Exit code = 0x80072F8F
2015-11-24    11:33:40:019    1004    eec    Agent    *********
2015-11-24    11:33:40:019    1004    eec    Agent    **  END  **  Agent: Finding updates [CallerId = AutomaticUpdates]
2015-11-24    11:33:40:019    1004    eec    Agent    *************
2015-11-24    11:33:40:019    1004    eec    Agent    WARNING: WU client failed Searching for update with error 0x80072f8f
2015-11-24    11:33:40:019    1004    11e8    AU    >>##  RESUMED  ## AU: Search for updates [CallId = {41482C00-1FF6-4B66-9F31-560B9F8C9877}]
2015-11-24    11:33:40:019    1004    11e8    AU      # WARNING: Search callback failed, result = 0x80072F8F
2015-11-24    11:33:40:019    1004    11e8    AU      # WARNING: Failed to find updates with error code 80072F8F
2015-11-24    11:33:40:019    1004    11e8    AU    #########
2015-11-24    11:33:40:019    1004    11e8    AU    ##  END  ##  AU: Search for updates [CallId = {41482C00-1FF6-4B66-9F31-560B9F8C9877}]
2015-11-24    11:33:40:019    1004    11e8    AU    #############
2015-11-24    11:33:40:019    1004    11e8    AU    Successfully wrote event for AU health state:0
2015-11-24    11:33:40:019    1004    11e8    AU    AU setting next detection timeout to 2015-11-24 22:33:40
2015-11-24    11:33:40:019    1004    11e8    AU    Setting AU scheduled install time to 2015-11-25 03:00:00
2015-11-24    11:33:40:019    1004    11e8    AU    Successfully wrote event for AU health state:0
2015-11-24    11:33:40:019    1004    11e8    AU    Successfully wrote event for AU health state:0
2015-11-24    11:33:44:730    1004    eec    Report    REPORT EVENT: {D5DA21B2-CEF4-4B70-923A-B7B29F092A25}    2015-11-24 11:33:39:723-0600    1   148    101    {D67661EB-2423-451D-BF5D-13199E37DF28}    1    80072f8f    SelfUpdate    Failure    Software Synchronization    Windows Update Client failed to detect with error 0x80072f8f.
2015-11-24    11:33:44:730    1004    eec    Report    REPORT EVENT: {89A38A19-5FE3-4DA2-943B-8286B4F25FC0}    2015-11-24 11:33:40:019-0600    1   148    101    {D67661EB-2423-451D-BF5D-13199E37DF28}    1    80072f8f    SelfUpdate    Failure    Software Synchronization    Windows Update Client failed to detect with error 0x80072f8f.
2015-11-24    11:33:44:777    1004    eec    Report    CWERReporter::HandleEvents - WER report upload completed with status 0x8
2015-11-24    11:33:44:777    1004    eec    Report    WER Report sent: 7.6.7601.19046 0x80072f8f(0) 67661EB-2423-451D-BF5D-13199E37DF28 Scan 1 0 SelfUpdate {3DA21691-E39D-4DA6-8A4B-B43877BCB1B7} 0
2015-11-24    11:33:44:808    1004    eec    Report    CWERReporter::HandleEvents - WER report upload completed with status 0x8
2015-11-24    11:33:44:808    1004    eec    Report    WER Report sent: 7.6.7601.19046 0x80072f8f(0) 67661EB-2423-451D-BF5D-13199E37DF28 Scan 1 0 SelfUpdate {3DA21691-E39D-4DA6-8A4B-B43877BCB1B7} 0
2015-11-24    11:38:41:598    1004    eec    PT    WARNING: Cached cookie has expired or new PID is available
2015-11-24    11:38:41:598    1004    eec    PT    Initializing simple targeting cookie, clientId = 0a7b8995-9dc7-4ada-9726-66b64c76d791, target group = , DNS name = nm-it-steve2.semo.health
2015-11-24    11:38:41:598    1004    eec    PT      Server URL = https://ITSERV1.semo.health:8531/SimpleAuthWebService/SimpleAuth.asmx
2015-11-24    11:38:41:614    1004    eec    Misc    WARNING: Send failed with hr = 80072f8f.
2015-11-24    11:38:41:614    1004    eec    Misc    WARNING: SendRequest failed with hr = 80072f8f. Proxy List used: <(null)> Bypass List used : <(null)> Auth Schemes used : <>
2015-11-24    11:38:41:614    1004    eec    Misc    FATAL: SOAP/WinHttp - SendRequest: SendRequestUsingProxy failed. error 0x80072f8f
2015-11-24    11:38:41:614    1004    eec    PT      + Last proxy send request failed with hr = 0x80072F8F, HTTP status code = 0
2015-11-24    11:38:41:614    1004    eec    PT      + Caller provided credentials = No
2015-11-24    11:38:41:614    1004    eec    PT      + Impersonate flags = 0
2015-11-24    11:38:41:614    1004    eec    PT      + Possible authorization schemes used =
2015-11-24    11:38:41:614    1004    eec    PT    WARNING: GetAuthorizationCookie failure, error = 0x80072F8F, soap client error = 5, soap error code = 0, HTTP status code = 200
2015-11-24    11:38:41:614    1004    eec    PT    WARNING: Failed to initialize Simple Targeting Cookie: 0x80072f8f
2015-11-24    11:38:41:614    1004    eec    PT    WARNING: PopulateAuthCookies failed: 0x80072f8f
2015-11-24    11:38:41:614    1004    eec    PT    WARNING: RefreshCookie failed: 0x80072f8f
2015-11-24    11:38:41:614    1004    eec    PT    WARNING: RefreshPTState failed: 0x80072f8f
2015-11-24    11:38:41:614    1004    eec    PT    WARNING: PTError: 0x80072f8f
2015-11-24    11:38:41:614    1004    eec    Report    WARNING: Reporter failed to upload events with hr = 80072f8f.
-----------------------------------------------------------------------------------------------------------

In other threads addressing this same error code, I've seen discussions talking about certificate issues and incorrect proxy settings. Unfortunately, my experience working with servers is very limited. I have been hesitant to jump in and make many settings changes because I don't want to break other services that this machine is hosting. I'm not sure if either of those issues apply to my situation. If so, I am unsure which solution to attempt first. I would greatly appreciate any pointers.




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