To finish off the marathon troubleshooting session I've had lately I've finally fixed the last lingering software update sync problem. This problem was noticed by the following symptoms:

I was seeing this error in the wsyncmgr.log over and over.

Failed to sync update XXXXXXXXXXXXXXXXXXXXX. Error: The Microsoft Software License Terms have not been completely downloaded and cannot be accepted. Source: Microsoft.UpdateServices.Internal.BaseApi.SoapExceptionProcessor.DeserializeAndThrow 

These events were showing up in the Application event log:

Event ID: 2 - Content file download failed. Reason: Value does not fall within the expected range. Source File: /msdownload/update/v5/eula/xpsp2eula_chs.txt Destination File: D:\Sources\WsusContent\3F\257205304B7517CD24386B2D997F74743DC6E73F.txt. Event ID: 7 - The server is failing to download some updates. 

These lines were constantly coming up in the C:\Program Files\Update Services\LogFiles\SoftwareDistribution.log.

WsusService.15 ContentSyncAgent.SetProxySettings   Value does not fall within the expected range. WsusService.15  EventLogEventReporter.ReportEvent   EventId=364,Type=Error,Category=Synchronization,Message=Content file download failed. Reason: Value does not fall within the expected range. Source File: /msdownload/update/v5/eula/officefilevalidation_eula_bg-bg-950bcb06-a2aa-4b25-bae4-2c198be23859.txt Destination File: D:\Sources\WsusContent\C5\CC06CFA16ED105D62526DBDD724A27F0A6A57FC5.txt. Warning w3wp.3  SoapExceptionProcessor.SerializeAndThrow    Discarding stack trace for user APOLLO\SERVER$, IP Address xxx.xxx.xxx.xxx, exception System.InvalidOperationException: The Microsoft Software License Terms have not been completely downloaded and cannot be accepted. Warning w3wp.40 SoapUtilities.CreateException   ThrowException: actor = http://wsusserver:8530/ClientWebService/client.asmx, ID=9e952ee5-8337-4f24-a76f-75c212cd27ba, ErrorCode=InvalidCookie, Message=, Client=? 

Microsoft support couldn't easily fix this and forced me to open a new ticket. Since the client used a proxy for all Internet traffic, they blamed it on the proxy. I refused to open another ticket and decided to look into it myself. Luckily, just after a few minutes of Googling, I came across the KB2838998 hotfix, downloaded, installed, rebooted the server with the SUP role on it, tried the sync again and worked like a champ!

I sure as hell hope next week my days go back to normal! I didn't get to write any cool PowerShell scripts!

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