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Windows Updates over VPN

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Last Modified: 2015-08-10
Unable to update Win8.1 devices over VPN - devices appear in SCCM, so are SEEN by SCCM/WSUS.

Extract of windowsupdate.log from client device:

2015-07-21      11:07:27:931       420      10a0      Agent        * Include potentially superseded updates
2015-07-21      11:07:27:931       420      10a0      Agent        * Online = Yes; Ignore download priority = Yes
2015-07-21      11:07:27:931       420      10a0      Agent        * Criteria = "(DeploymentAction=* AND Type='Software') OR (DeploymentAction=* AND Type='Driver')"
2015-07-21      11:07:27:931       420      10a0      Agent        * ServiceID = {3DA21691-E39D-4DA6-8A4B-B43877BCB1B7} Managed
2015-07-21      11:07:27:931       420      10a0      Agent        * Search Scope = {Machine}
2015-07-21      11:07:27:931       420      10a0      Agent        * Caller SID for Applicability: S-1-5-18
2015-07-21      11:07:27:931       420      10a0      Agent        * RegisterService is set
2015-07-21      11:07:27:931       420      10a0      EP      Got WSUS Client/Server URL: "http://servername.local:8530/ClientWebService/client.asmx"
2015-07-21      11:07:28:431       420      10a0      PT      +++++++++++  PT: Synchronizing server updates  +++++++++++
2015-07-21      11:07:28:431       420      10a0      PT        + ServiceId = {3DA21691-E39D-4DA6-8A4B-B43877BCB1B7}, Server URL = http://servername.local:8530/ClientWebService/client.asmx
2015-07-21      11:07:28:431       420      10a0      PT      WARNING: Cached cookie has expired or new PID is available
2015-07-21      11:07:28:431       420      10a0      EP      Got WSUS SimpleTargeting URL: "http://servername.local:8530"
2015-07-21      11:07:28:431       420      10a0      IdleTmr      WU operation (CAuthorizationCookieWrapper::InitializeSimpleTargetingCookie) started; operation # 6; does use network; is at background priority
2015-07-21      11:07:28:431       420      10a0      PT      Initializing simple targeting cookie, clientId = 033c840a-86a4-43e4-95f1-ce649aed8dfc, target group = , DNS name = device.domain.local
2015-07-21      11:07:28:431       420      10a0      PT        Server URL = http://servername.local:8530/SimpleAuthWebService/SimpleAuth.asmx
2015-07-21      11:07:49:478       420      10a0      WS      WARNING: Nws Failure: errorCode=0x803d0006
2015-07-21      11:07:49:478       420      10a0      WS      WARNING: Original error code: 0x80072ee2
2015-07-21      11:07:49:478       420      10a0      WS      WARNING: Error string with resource id '0x81' is not found for the language id '0x809'.
2015-07-21      11:07:49:478       420      10a0      WS      WARNING: Could not get error string (errorCode=0x80073b01)
2015-07-21      11:07:49:478       420      10a0      WS      WARNING: MapToSusHResult mapped Nws error 0x803d0006 to 0x8024401c
2015-07-21      11:07:49:478       420      10a0      WS      WARNING: Web service call failed with hr = 8024401c.
2015-07-21      11:07:49:478       420      10a0      WS      WARNING: Current service auth scheme='None'.
2015-07-21      11:07:49:478       420      10a0      WS      WARNING: Proxy List used: '(null)', Bypass List used: '(null)', Last Proxy used: '(null)', Last auth Schemes used: 'None'.
2015-07-21      11:07:49:478       420      10a0      WS      FATAL: OnCallFailure failed with hr=0X8024401C
2015-07-21      11:07:49:478       420      10a0      WS      WARNING: NWS retry 1 for transient error 0x8024401C
2015-07-21      11:08:12:514       420      10a0      WS      WARNING: Nws Failure: errorCode=0x803d0006
2015-07-21      11:08:12:514       420      10a0      WS      WARNING: Original error code: 0x80072ee2
2015-07-21      11:08:12:514       420      10a0      WS      WARNING: Could not get error string (errorCode=0x80073b01)
2015-07-21      11:08:12:514       420      10a0      WS      WARNING: MapToSusHResult mapped Nws error 0x803d0006 to 0x8024401c
2015-07-21      11:08:12:514       420      10a0      WS      WARNING: Web service call failed with hr = 8024401c.
2015-07-21      11:08:12:514       420      10a0      WS      WARNING: Current service auth scheme='None'.
2015-07-21      11:08:12:514       420      10a0      WS      WARNING: Proxy List used: '(null)', Bypass List used: '(null)', Last Proxy used: '(null)', Last auth Schemes used: 'None'.
2015-07-21      11:08:12:514       420      10a0      WS      FATAL: OnCallFailure failed with hr=0X8024401C
2015-07-21      11:08:12:514       420      10a0      WS      WARNING: NWS retry 2 for transient error 0x8024401C
2015-07-21      11:08:35:545       420      10a0      WS      WARNING: Nws Failure: errorCode=0x803d0006
2015-07-21      11:08:35:545       420      10a0      WS      WARNING: Original error code: 0x80072ee2
2015-07-21      11:08:35:545       420      10a0      WS      WARNING: Could not get error string (errorCode=0x80073b01)
2015-07-21      11:08:35:545       420      10a0      WS      WARNING: MapToSusHResult mapped Nws error 0x803d0006 to 0x8024401c
2015-07-21      11:08:35:545       420      10a0      WS      WARNING: Web service call failed with hr = 8024401c.
2015-07-21      11:08:35:545       420      10a0      WS      WARNING: Current service auth scheme='None'.
2015-07-21      11:08:35:545       420      10a0      WS      WARNING: Proxy List used: '(null)', Bypass List used: '(null)', Last Proxy used: '(null)', Last auth Schemes used: 'None'.

Feels like a proxy/firewall issue, but could od with some Expert guidance please?
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