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Is SBS 2008 worth persevering with?

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I am looking after an SBS 2008 server in a small local organisation - but just seem to run into a never ending sequence of problems.  Take WSUS (please !).  It wasn't working and just generated error logs that were both huge and incomprehensible. I won't bore you with them as I decided the best way forward would be to uninstall WSUS and reinstall it from scratch.  Part of the problem may have been with Windows Updates.  I discovered that no updates had been applied to this server in the last 18 months.  This wasn't surprising as, when I ran the standard "check for updates" option via Control Panel / Windows Updates, there were no outstanding updates reported.  Still, I managed to detect the outstanding 70 or 80 of the blighters and get them installed.  As far as I can tell, my SBS 2008 installation was then up to date.

But, today, when I reinstalled WSUS there was a most curious train of events, roughly as follows:

1.  Run WSUSsetup.exe to reinstall WSUS 3.0 SP1 

2.  See various success messages displayed - e.g. "Successfully connected to SQL server instance <myserver>\MICROSOFT\##SSEE

3.  Select the option to create a WSUS 3.0 SP1 web site at http://<myserver>:8530

4.  See a success message saying, "You have successfully completed the Windows Server Update Services 3.0 SP1 Set-up Wizard".

BUT, BUT (splutter, splutter), a split second later this same wizard displayed the following error message:

"An unexpected error occurred, and this wizard must be closed.  You may restart WSUS Server Configuration Wizard from the Options Page in the WSUS 3.0 Console".

Before doing so, I went back to Control Panel / Windows Updates to see if the WSUS mechanism for checking for Windows Updates was now working.  It wasn't!  I still got the same old "Windows Update encountered an unknown error - code 80244008".

So, while still in the Control Panel / Windows Updates, I checked for updates using the non-WSUS option.  This offered me WSUS 3.0 SP2 which I downloaded and installed.  But I got an error saying that I was missing "Microsoft Report Viewer 2008 Redistributable" - without which I wouldn't be able to run the WSUS Admin GUI.

So, I installed various further Windows Updates (including the above missing viewer) and, as far as I can tell, my system really is now up to date.

Now to the latest problems.

I started up the WSUS Console and, happily, could see my server listed (joy upon joy).

I clicked on Options and then WSUS Server Configuration Wizard (i.e. to see if the Wizard - which had failed above - could now be restarted and completed).  The first few screens of the wizard were fine.  I selected Microsoft Update as my upstream server, didn't need to define a Proxy server etc.

But, when I reached the screen with the "Start Connecting" button, and clicked on it, I received the following message:

"WebException: The request failed with the error message:
--
<html><head><title>Object moved</title></head><body>
<h2>Object Moved to <a
href=

etc etc.

Sorry I am unable to paste the whole message.  Bizarrely, SBS 2008 decided to display it in a window where copy/paste has been disabled.

WSUS isn't my only problem.  If I start up IE and enter the following URL - "http://companyweb", I get an error that it failed to start due to a "compilation error".  Compilation error?  What compilation error?  I've no idea!


Also, when looking at logs, there seem to be a lot of occasions where something failed to execute due to a lack of permissions to write to various temp file.  Yet my user on this server has full admin rights!

I have entitled this post "Is SBS 2008 worth persevering with?" because I just get the feeling that there is an underlying issue which is causing all these problems.  I have no way of determining what this is.  

Does anyone have any ideas?  My best idea so far is to dump SBS 2008 and find something sensible to replace it.

What would be sensible?


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