Small Business Server 2008 Top Issues

Small Business Server 2008 Top Issues

Small Business Server 2008 - Top Issues Seen in the Community

When working with SBS you’ll find that you’ll tend to see some issues in the forums and newsgroups again and again.  So to help with the ability for those searching for answers to find solutions, here is a recap of some of the top issues we see in the newsgroups and forums.  As you’ll soon see, most of these issues were long ago discussed on the official SBS blog located at  With any issue impacting SBS your first thought should be “Hey, I remember reading something about that on the SBS blog”.  You then should go to and search back. 
But here is a recap of some of the issues all of us would like to see a lot less of and I’m sure you would as well.

1.      Symptoms:  SBS 2003 to SBS 2008 migration fails due to “dirty” active directory that was not cleaned up before attempting the migration.

a.      Reason:  SBS 2003 being a single domain controller can work for YEARS being in an active directory journal wrap condition caused by a dirty shut down of AD and never have issues.  However when you go to attempt a migration it will fail.

b.      Solution:  Always follow the SBS migration keys to success blog post SBS 2008 Migrations from SBS 2003 – Keys to Success and run the SBS 2003 best practices analyzer and the Microsoft IT Environment Health Scanner to test for journal wrap issues.  If you do have the Journal wrap error, all you need to do is set a registry entry just as the event error tells you to do with a value of “1” and it will fix itself.

2.      Symptoms:  Other Migration failures

a.      Reason:  Migrations can have some potential reasons for failure but these days they follow into a couple of categories.

b.      Solution:  Read the as it documents the typical causes for issues.  As was listed earlier you should always review the “Keys to success” post and start there with any migration and go through each.  The other issue I see as a sticking point in migrations is public folder replications which may be caused by using a smart host which blocks the replication. Another sticking point may be not running the migration preparation tool or having a mismatch and using SP1 media for the migration preparation tool, and using SP2 media to install the server.  Ensure you use the SAME media to match up the prep tool with the built server.  You can review a demo here to see what should occur during a migration -  .  One thing to keep in mind to ensure that you have a way back is to have a good backup.  In a perfect world you would restore the SBS 2003 back to it’s original condition before you started the migration.  The reality is for most of us is that your best bet you can do is to ensure you have a System State backup and you restore that.  Then you go back into your Active Directory ensuring that any traces of the new server are not found in your active directory and start the migration over.  From this point of clean up you have 21 days again to do the migration.

3.      Symptoms:  Migrations tasks are bypassed or not completed.

a.      Reason:  The process to migrate from SBS 2003 to SBS 2008 is do-able but it’s quite honestly a long process.  Thus there is a natural tendency to skip over reading the documentation and the process and try to circumvent some of the steps.

b.      Solution:  Don’t cut corners.  Download the documents and especially the migration checklist, and review other community guidance.  The process of migration is totally do-able as long as you read, understand the process, and set up a practice with a demo domain first.  There are third party migration sites as well that can help you through the process as well.  Whether you decide to do a clean migration and totally reset up the entire network a Microsoft migration or a third party migration is up to you.  Generally speaking most feel that a small client (approximately 5 or so workstations) may benefit from a clean setup especially if you’ve never touched their server before and you want to start fresh.  Anything in the 25 or above range should not be done during a clean install as you impact the desktops too much.  I blogged a dry run of my entire migration process, stuck the content here, and the tagged blog entries are here -   and here -


4.      Symptoms:  Reinstalling SBS 2008 after a bad install, a bad migration attempt, etc.

a.      Reason:  You install SBS 2008 and believe you’ve had a bad installation.  Therefore you decide to reinstall all over again.

b.      Solution:  There are bad installs and then there are innocuous error messages that make you think you’ve had a bad install when you really haven’t.  Let’s discuss some that are benign and can be ignored and some that need to be addressed.

                                                              i.      You choose to install updates during the install of SBS 2008 and the error message indicates a failure of the updates during the install.  This is a benign error that you should not reinstall your server for.  I honestly do not choose to install updates during the install process because I have installed before with a known media and the last thing I want to do is to install with a changed media set.  At this time there are absolutely no updates that directly impact the install process.  All of them are security updates that you can install after you have built the box.  You can safely install SBS 2008 with the media you have and patch it afterwards.  No security issues will occur with the shipped media you install with.

                                                            ii.      You choose to install updates after the install of SBS 2008 is complete and you find you cannot browse companyweb from the server or add Windows 7 clients to the domain using the connect wizard. There are fixes for things like this in SBS 2008 Update Rollups available from MU and WSUS so make sure you flip to MU (Microsoft update) or approve these updates in WSUS.  A priority update on the SBS 2008 (KB961048) will change the update rollups of the SBS platform to automatically get approved.  Remember the default patching condition of the server is that Security patches will automatically get approved, but NOT automatically installed.  It’s up to you to go to the server and install via the update icon showing in the corner any patches offered up there.  Exchange rollups are not automatically approved so don’t forget to either manually visit Microsoft Update (not just Windows update), or go to the update tab in the console and approve updates you see there.

                                                          iii.      You choose to install WSUS 3 Service pack 2 and it “breaks” the WSUS integration with the SBS 2008 console.  I use “breaks” in quotes because I honestly don’t feel this is a real “breakage” since it’s very easy to put it back into a working condition.  For the WSUS integration you just need to ensure that you choose “All products” as the category of patches.  This will not download more patches than you have in your network and will merely ensure that the detection of new patches, new machines will work properly.  WSUS is a component that I have uninstalled and reinstalled several times without issue following the instructions here:

                                                           iv.      There are times that a reinstall all over again may be correct, but then there are many times that it’s not needed.  You may just need to install it several times in advance to practice before you install it for a client.  Your first install should never be for a client.  Review these demos ahead of time - and practice on real hardware or hyperV virtual platform.

5.      Symptoms:  Folder Redirection doesn’t work as expected.

a.      Reason:  Folder redirection is not working as expected due to incorrect settings on the server.  Additionally during the migration of SBS 2003 to SBS 2008 you fail to properly move the redirected folders that were set on the SBS 2003 server to the SBS 2008.

b.      Solution:  You may need to manually review the redirected folders instructions on the SBS 2008 to ensure that the NTFS permissions are properly set - .  To ensure that you do not fail to migrate redirected folders from the original SBS 2003, during the migration from SBS 2003 to SBS 2008 right before you decommission the SBS 2003 server, shut it off for a day or so to see if you have forgotten to move data, printers and importantly this step – redirected folders.

6.      Symptoms:  Network card drivers may need updating or tweaking to ensure proper functionality.

a.      Reason:  Since the advent of the advanced networking included in Windows 2003 Service Pack 2 you either love Offloading or hate it.  When it works, it speeds up your server and works beautifully.  When it doesn’t, the network can act a bit strangely and possibly have speed issues, you may also see issues with BITS, VSS issues, RRAS and WMI all documented here – BITS, IAS VSS and RRAS may stop responding on SBS 2008 with a particular NIC driver . 

b.      Solution:  Always start out first by examining to see if you have the latest network card driver.  Once you have that in place as well as Windows 2008 SP2 installed, determine if you want to disable Large Send Offload and Task Offloading in the properties of the nic or RSS, Tcpa and DisableTaskOffload as documented in the blog post.


7.      Symptoms:  Outlook prompts over and over again for credentials

a.      Reason:  In December of 2009 the MSRC announced a widespread release of KB973917 .  This update impacts the kernel mode authentication used on SBS 2008 and the symptom is that Outlook prompts for credentials.

b.      Solution:  Review the SBS blog post that specifically covers this issue:  Outlook 2007 Credential Prompts in Small Business Server 2008    If you had kept your SBS 2008 server reasonably up to date in patching, you’d honestly never see this issue as the fix was included in update rollup 8 for Exchange 2007 Service pack 1.  At this point in time, I’d recommend following the blog or installing Exchange 2007 Service pack 2 using KB974271.

8.      Symptoms:  Microsoft Exchange services fail to start.  Server hangs at applying computer settings.  Network icons show as offline.  Event 2114. 2601, 2102, 2114, 8197, 7005, 7044 and/or 7024.

a.      Reason:  You unchecked the IPv6 protocol from the network interface card in your SBS 2008 server after reading some Windows 2008 guidance that said you didn’t need IPv6.

b.      Solution:  Review the SBS blog post that specifically covers this issue: Issues After disabling IPv6 on your NIC on SBS 2008.   Don’t uncheck the IPv6 protocol as you really do need it.  Exchange 2007 in particular is very sensitive to having this protocol disabled and will complain very loudly and with very painful symptoms.  If you truly have to disable IPv6 for reasons unknown to me, then follow that blog post to disable it the RIGHT way for a SBS 2008 server.  Merely unchecking the box is not the right way. 


9.      Symptoms:  Email not being sent, C drive out of space.

a.      Reason:  Due to excessive and unnecessary WSUS/IIS log files being saved on the C drive, the space used by these logs will grow so much and start impacting the ability of Exchange to send email. If you have a default SBS 2008, the WSUS administration site pumps out huge amount of unnecessary log files.  If the server has been in production for a year or more, you might see an issue where these log files have grown so large that they are now interfering with Email being sent. 

b.      Solution:  To fix this, go into the IIS console and disable the IIS logging for the WSUS administration site and delete the log files as documented on the SBS blog:  Recovering disk space on the drive C: in Small Business Server 2008.  And don't forget to "Run as admin" when performing tasks as it will show you the true use of drive C:

10.  Symptoms:  Multiple nics enabled on SBS 2008 cause the SBS 2008 networking wizards not to work.

a.      Reason:  The SBS 2008 wizards were built with the assumption that you would only use one nic.  Thus if you attempt to do network teaming wizards will not run and the Support personnel will ask you to de-team the box before they work with you.  NIC teaming is not a supported scenario for SBS 2008  (see – Returning Small Business Server 2008 to a Supported Network Topology ) and you’ll need to remove it to get the server into a supported topology.

b.      Solution:  This is one of those tricky situations where you’ll need to set the box up and always return it to a supported single nic solution when installing and dealing with support.


11.  Symptoms:  Accessing the SBS websites, like OWA and RWW doesn’t work as it should due to the fact that the Internet Address management wizard was never run. 

a.      Reason:  Some people manually set up the server and don’t realize there is a wizard on the box to configure web publishing.  Thus accessing the SBS websites isn’t quite right and may impact the server’s working condition.

b.      Solution:  The SBS blog has several posts regarding the Internet Address management Wizard: Introducing the Internet Address Management Wizard part 1 and Part two of the series and Part three .  Also review how the run the “Fix my network wizard  can help in your situation. If you wish to use a trusted certificate, review the Add A Trusted Certificate Wizard blog post for installing the certificate instead of the step from the provider.  In SBS 2008, the trusted certificate should be installed on the SBS Web Applications website and not the Default Web Site. If for some reason, you get stuck, here’s the blog post on how to install the certificate manually.


12.  Symptoms:  In troubleshooting issues with Remote Web Workplace or Outlook prompting for credentials you adjust the IIS authentication method incorrectly.

a.      Reason:  Chances are the reason you hit this issue is that you didn’t run the “Fix my network wizard” that is in the console and instead decided to poke and tweak. 

b.      Solution:  Again your best bet is run the “Fix my network wizard” – Introduction to the Fix My Network Wizard .  If that doesn’t fix things up and you need to take more of a look under the hood there are several suggestions I would make.  The first one would be is to install a virtual SBS 2008 somewhere as a baseline and compare your existing SBS with the baseline version.  Secondly review these two blog posts  -- one that talks about manually adjusting the Windows authentication tab to Negotiate(Kerberos) Known Issues after Installing IE8 on Small Business Server 2008 and the Vista clients that are joined to the SBS domain -  and the other that discusses some of the common issues for the Remote Web Workplace – Common Remote Web Workplace (RWW) Connect to a Computer Issues in SBS 2008 -    Item number 4 in particular should be reviewed.  Also check in item number 8, that client certificates should be set to ignore the SSL settings on the RPC virtual directory.

13.    Symptoms:  Loss of default gateway on SBS 2008.

a.      Reason:  Certain actions taken on the SBS 2008 box involving disabling and enabling network cards and then running the connect to internet wizard will cause the default gateway to be lost after reboot.  If you navigate to HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Services\Tcpip\Parameters\Interfaces\<GUID>\DefaultGateway and double click the Default Gateway value.  See if there is a blank line before the actual default gateway IP.

b.      Solution:  Edit the default gateway in the registry as it should be an apply KB 973243.  While the hotfix says it is for Vista 64bit, the same code is for Windows Server 2008 as well.  The default gateway is missing on a computer that is running Windows Server 2008 or Windows Vista after the computer restarts if the default gateway is set by using the Netsh command:;EN-US;973243 This hotfix will prevent the issue from occurring again.


14.  Symptom:  Wizards fail to run as expected.

a.      Reason:  HyperV role is enabled on SBS 2008.

b.      Solution:  Remove the HyperV role on the SBS 2008.  While SBS 2008 is supported in HyperV, it is NOT supported to install the HyperV role on SBS 2008.  If you purchase SBS 2008 premium you can take the Windows 2008 standard media included in the premium version, install it as a base Windows server.  Then add the HyperV role.  Now you can install the SBS 2008 server and then install the Windows 2008 media as a second server.  This is called a 1+1 licensing which is allowed for HyperV.

15.  After a recent security update, SharePoint fails to work as expected.

a.  Reason:  On some (not all) servers, the recent SharePoint security update will not complete the update.  On others, you may have googled some information and changed the log in of the search service.  Don't do that.  You'll make your server go boom on updating with this patch. 

b.  Solution:  Follow this blog post for ways around the issue.  In many cases merely running psconfig as noted there will solve the issue.  In others, change the account back to local service and rerun psconfig.

If none of these help you ANY issue with a security update is a free support call to Microsoft.  Call 1-800-Microsoft or your local Microsoft office.  Indicate that you had an issue with a security update.

Did you get the idea from this post that the best thing you can do if you support SBS 2008 boxes is to sign up for the SBS blog updates?  To receive the updates in your RSS reader subscribe here -  I personally use IntraVnews to pull it into my Outlook rather than the native Outlook rss reader, but you can use Google reader as well.  If you are into twitter you can follow the SBS team here: Last but not least, check out the SBS 2008 forum.
So there you have it.  There’s a comprehensive listing of the top issues that I’m hoping we see less of now that you know about them!


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  • Eric Battalio edited Revision 8. Comment: Scoped "top issues" title to specific product.

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  • Ed Price MSFT edited Revision 4. Comment: Title case

  • Well written! I think we should make an article of DOs and DONT DOs on SBS that should cover all versions, I think that'll solve almost everyone's problems except for hardware issues... I'd be willing to contribute if anyones interested.

  • Have you seen the stuff?

  • Susan Bradley edited Revision 6. Comment: Editing for Font size

  • Eric Battalio edited Revision 8. Comment: Scoped "top issues" title to specific product.

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