Windows Update Client – Error Code 80244019

Issue Context

Multiple workstations connected to a Server2016 WSUSv10 server. Workstations are able to check in with WSUS and receive a list of available updates, but when clicking ‘Install’, the Windows Update client would fail for all updates after a few seconds.

Checking Windows Update Log

C:\Windows\WindowsUpdate.log
2018-03-27    08:09:18:404    1184    6cf8    DnldMgr    ***********  DnldMgr: New download job [UpdateId = {BC3D29C9-3F1D-4600-B2FB-17FF55D8BEC2}.201]  ***********
2018-03-27    08:09:18:426    1184    6cf8    DnldMgr      * BITS job initialized, JobId = {7295E98D-14CF-4207-A7AD-8E08305BCE03}
2018-03-27    08:09:18:430    1184    6cf8    DnldMgr      * Downloading from http://wsus-server.domain.com:8530/Content/49/EF5AB517E8E81E0C9FE4F8251C7C761722E45449.cab to C:\windows\SoftwareDistribution\Download\853e2e8b01969e74e5dbf4ea7a2d9e20\Windows6.1-KB4038779-x64.cab (full file).
2018-03-27    08:09:18:437    1184    6cf8    Agent    *********
2018-03-27    08:09:18:437    1184    6cf8    Agent    **  END  **  Agent: Downloading updates [CallerId = AutomaticUpdatesWuApp]
2018-03-27    08:09:18:437    1184    6cf8    Agent    *************
2018-03-27    08:09:18:437    1184    37b0    DnldMgr    WARNING: BITS job {7295E98D-14CF-4207-A7AD-8E08305BCE03} failed, updateId = {BC3D29C9-3F1D-4600-B2FB-17FF55D8BEC2}.201, hr = 0x80190194, BG_ERROR_CONTEXT = 5
2018-03-27    08:09:18:438    1184    37b0    DnldMgr      Progress failure bytes total = 43728287, bytes transferred = 0
2018-03-27    08:09:18:438    1184    37b0    DnldMgr      Failed job file: URL = http://wsus-server.domain.com:8530/Content/49/EF5AB517E8E81E0C9FE4F8251C7C761722E45449.cab, local path = C:\windows\SoftwareDistribution\Download\853e2e8b01969e74e5dbf4ea7a2d9e20\Windows6.1-KB4038779-x64.cab
2018-03-27    08:09:18:442    1184    37b0    DnldMgr    Error 0x80244019 occurred while downloading update; notifying dependent calls.
2018-03-27    08:09:18:445    1184    4704    AU    >>##  RESUMED  ## AU: Download update [UpdateId = {3DE7A78A-5B97-4DF7-8BF6-36EBE20D3C75}]
2018-03-27    08:09:18:445    1184    4704    AU      # WARNING: Download failed, error = 0x80244019
2018-03-27    08:09:18:445    1184    4704    AU    Setting AU scheduled install time to 2018-03-28 07:00:00
2018-03-27    08:09:18:445    1184    4704    AU    Successfully wrote event for AU health state:0
2018-03-27    08:09:18:446    1184    4704    AU    Currently showing Progress UX client - so not launching any other client
2018-03-27    08:09:18:447    1184    6cf8    DnldMgr    *************
2018-03-27    08:09:18:447    1184    6cf8    DnldMgr    ** START **  DnldMgr: Downloading updates [CallerId = AutomaticUpdatesWuApp]
2018-03-27    08:09:18:447    1184    6cf8    DnldMgr    *********
2018-03-27    08:09:18:447    1184    6cf8    DnldMgr      * Call ID = {1521854B-8779-4C75-A2CC-4762E4932223}
2018-03-27    08:09:18:447    1184    6cf8    DnldMgr      * Priority = 3, Interactive = 1, Owner is system = 1, Explicit proxy = 0, Proxy session id = 1, ServiceId = {3DA21691-E39D-4DA6-8A4B-B43877BCB1B7}
2018-03-27    08:09:18:447    1184    6cf8    DnldMgr      * Updates to download = 1
2018-03-27    08:09:18:447    1184    6cf8    Agent      *   Title = Security Update for Microsoft Silverlight (KB4023307)
2018-03-27    08:09:18:447    1184    6cf8    Agent      *   UpdateId = {96D2119C-C85D-4490-B58C-927D2EBE297C}.200
2018-03-27    08:09:18:447    1184    6cf8    Agent      *     Bundles 1 updates:
2018-03-27    08:09:18:447    1184    6cf8    Agent      *       {2A77AFE3-1E82-48DA-B817-2F69E2C8218C}.200

and…

2018-03-27    08:09:19:127    1184    6cf8    Report    REPORT EVENT: {93D4A6F9-00BA-4D6F-B2A1-E7C3F369272D}    2018-03-27 08:09:15:496-0400    1    161    101    {F97B770A-4DB7-4633-8F2F-ECF75FE36C3F}    204    80244019    AutomaticUpdatesWuApp    Failure    Content Download    Error: Download failed.
2018-03-27    08:09:19:127    1184    6cf8    Report    REPORT EVENT: {E81A8073-E072-4D38-BAB0-ABB2C4994EDC}    2018-03-27 08:09:15:572-0400    1    161    101    {0958DD0C-92B0-45D3-8588-C4034E52ACAA}    201    80244019    AutomaticUpdatesWuApp    Failure    Content Download    Error: Download failed.
2018-03-27    08:09:19:127    1184    6cf8    Report    REPORT EVENT: {FC7582B6-0CCB-4128-93F4-B12B43DDD8E7}    2018-03-27 08:09:15:635-0400    1    161    101    {BD312012-799E-4B68-9AF2-F9EEE93E86AA}    205    80244019    AutomaticUpdatesWuApp    Failure    Content Download    Error: Download failed.

Checking Windows Event Logs

Log Name:      Application
Source:        Windows Server Update Services
Date:          3/28/2018 4:21:31 PM
Event ID:      12072
Task Category: 9
Level:         Error
Keywords:      Classic
User:          N/A
Computer:      wsus-server.domain.com
Description:
The WSUS content directory is not accessible.
System.IO.DirectoryNotFoundException: Could not find a part of the path 'D:\WSUSContent\WsusContent\anonymousCheckFile.txt'.
   at System.IO.__Error.WinIOError(Int32 errorCode, String maybeFullPath)
   at System.IO.FileStream.Init(String path, FileMode mode, FileAccess access, Int32 rights, Boolean useRights, FileShare share, Int32 bufferSize, FileOptions options, SECURITY_ATTRIBUTES secAttrs, String msgPath, Boolean bFromProxy, Boolean useLongPath, Boolean checkHost)
   at System.IO.FileStream..ctor(String path, FileMode mode, FileAccess access, FileShare share)
   at System.IO.FileInfo.Open(FileMode mode, FileAccess access, FileShare share)
   at Microsoft.UpdateServices.Internal.HealthMonitoring.HmtWebServices.CheckContentDirWebAccess(EventLoggingType type, HealthEventLogger logger)

Issue Resolution

Because of these errors, I began checking for incorrect references or permissions to where the WSUSContent folder is located in the WSUS configuration.

Checking the Registry

Notice the ‘ContentDir’ value is D:, which is technically an invalid path. A backslash is required.

I updated the value to D:\

Checking IIS

IIS → WSUS Administration → Content → Advanced Settings

Again, notice the value of ‘Physical Path’ is set to D:WsusContent\, which is an invalid path.

I updated the value to D:\WsusContent\.

Once these values were updated, my Windows Update Clients were able to download and install the pending updates.

The reason both of these locations included an incorrect path was because of how the WSUS server was installed. During the WSUS setup wizard, you are prompted for a path to store downloaded updates. If you enter a value like D:, the value will be propagated to the above locations as-is. No backslash will be appended if missing.

Other Attempted Resolution

Below is another fix I tried, which ultimately did not resolve the issue. Including it here for reference.

Recommended to run wsusutil /reset

https://social.technet.microsoft.com/Forums/ie/en-US/08e32b9c-a83d-41c9-9816-c1ed5e719c5d/wsus-client-side-error-log-80244019-80071b6e?forum=winserverwsus

cd 'c:\Program Files\Update Services\Tools'
wsusutil reset

This process takes place within the SQL server. Progress (or at least ‘is this still running?’) can be seen in Task Manager:

I am not 100% sure how long this process took, but after ~24 hours, the issue was still not resolved.