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  • Server 2008 ESU: questions, glitches, experience so far

    Posted on lawrenceB Comment on the AskWoody Lounge

    Home Forums Admin IT Lounge Server 2008 ESU: questions, glitches, experience so far

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      • #2111664 Reply
        AskWoody Lounger

        Hey folks.

        Anybody else installing the Server 2008/Server 2008 R2 ESU MAK?  Having some issues.

        Server 2008 R2: No issues. MAK installs and activates. slmgr /dlv shows license. ESU test update KB4528069 installs just fine.

        Windows Web Server 2008: Is this supported for ESU? MAK installs successfully with /ipk, shows up with /dlv, but cannot be activated (“Activation failed.”)  Assuming MS would not intentionally exclude this version of 2008. Documentation for ESU doesn’t mention it explicitly, however.

        Server 2008 x64: MAK installs, but doesn’t show with ‘slmgr /dlv’. Activates fine, but still not visible with slmgr/dlv. Nevertheless, ESU test update KB45280801 installs fine.

        Server 2008 x86/32-bit: MAK installs and activates fine, but never shows with slmgr /dlv. Just like with Server 2008 x64, above. However, there’s no 32-bit Server 2008 ESU test update, so no way to tell whether these systems will be able to grab security updates next month or not.

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      • #2111688 Reply
        Da Boss


        I have no idea what’s going on. Is there a Server ESU expert in the house?

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      • #2111691 Reply
        AskWoody Lounger

        lawrenceB, does your web server have a path to the Internet for activation? (I know that sounds crazy – it’s a web server – but if it’s behind a firewall that blocks or filters all but 80/443, or behind a load balancer… well, you might need to proxy it out just for activation’s sake.

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      • #2111695 Reply

        Would you happen to have a Server Essentials or Small Business Server on the same domain? If so, you are violating the license and this can cause this.


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      • #2111730 Reply
        AskWoody Lounger

        jabeautty: Thanks, good thought, but no, these machines have full internet access.

        Deanna: No, neither of those, thanks for the suggestion though.

        Considering it’s on all 3 of my “Windows Web Server 2008 R2″ servers, and none of my normal R2 Std/Ent servers, I really wonder  if microsoft just forgot to test ESU on this edition.

        I’ll pull some event logs when I have a second and post them, maybe that will shed more light.

      • #2112249 Reply

        hardly anyone uses a 32bit version of Server 2008 nowadays, lawrenceB
        due to most server based machines running the commonly used 64bit version

        maybe the 32bit version of KB4528081 was never produced due to very low to nonexistent interest in 32bit Server 2008 usage

        • This reply was modified 2 months ago by EP.
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      • #2123874 Reply
        AskWoody Lounger

        Thanks EP,  looks like you’re correct about them not producing an ESU test update for 32-bit 2008. Confirmed by microsoft in the comments at

        So, my only remaining mystery: Windows Web Server 2008 R2 not activating with the 2008 ESU key. Will try to open a ticket with them. I really think they forgot to test this Edition with the ESU key. Or intentionally are not supporting it.

      • #2190169 Reply
        AskWoody Plus

        I don’t think Windows Web Server 2008/R2 is supported, and documentation that is provided simply says it is EOL where as other supported products have notes for ESU.

        I’m usually a lurker but I’ll at least share my experiences. For reference I’m a server patch manager for a large metro city. We had about 300 Legacy servers 2008 & R2. Of those about 15% would not do the online activation. Many of these were in the same cluster or on the same network with the same rules applied, so it wasn’t an issue of being blocked. Ended up using the phone activation web-app to do the activation. (This can be done by going through the phone process and then accepting the text message option, it will load you to a page you can use over and over to activate).

        Outside of the initial activation issues, the only problem is that after some of the servers installed the test patch and were rebooted the windows update services would get stuck in a “Starting” state. Trying to force stop it would get it stuck in a “Stopping” state. The fix was to disable the service altogether, reboot, remove the c:\windows\softwaredistribution folder, then set the service back to enabled (delayed) and start the service, then continue patching. This only occurred on about 3-5% of the servers.

        Everything else has been A-OK

      • #2211363 Reply

        Hello @lawrenceB

        Did you get any luck with the support? Is Windows Web Server 2008 R2 supported at all?

        Thank you.

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