Unlike the SBS2000 to SBS2003 upgrade process, the SBS2003 to SBS2008 procedures are clean.  The first thing you need is new hardware. 

NOTE: This process below is offered with no guarantees and we accept no liability.�
To keep an otherwise complex process simple, it is provided in a terse point form.

SBS 2003 to SBS 2008 Migration Process PREWORK

1. Backup the Existing SBS 2003 Server
2. Clean the SBS 2003 Server – remove/ archive (into local .PST) as much mail as possible
3. Run Windows Update on SBS2003 server and ensure ALL updates and Service Packs for Windows, Exchange and SharePoint have been installed
4. Raise AD Functional Level to highest possible
5. Make sure all of your programs work on Server 2008 (note that SBS2008 is 64 bit only!)
6. Move the SBS 2003 behind a firewall and disable ISA from SBS 2003
   • SBS 2008 does NOT ship with ISA or any other network edge firewall.
7. Ensure the SBS 2003 server is only using ONE network card and that it has a static address
8. Run MIGRATION PREPARATION TOOL (in the TOOLS folder on the SBS 2008 media?)
   1. This will require a reboot
9. Run the ANSWER FILE TOOL (SBSAfg.exe in the TOOLS folder on the SBS 2008 media)�
   1. Company info and Certificate Authority settings are optional and can be reconfigured after the install is completed
   2. Put sbsanswerfile.xml onto a flash drive or floppy (in the root… do not put it in a folder)

During the migration your network will look something like:
 

ACTUAL MIGRATION PROCESS

1. Start up the new hardware (which you are going to install SBS 2008) boot from the SBS 2008 media
   • Make certain you have put the sbsanswerfile.xml floppy or flash drive in the new server hardware BEFORE it boots
   • Note that this process is NOT undoable once started because the migration makes permanent changes to the original SBS 2003 server
   • This process can take more than an hour so don’t sweat it if it looks like is stuck for a while
2. After the new SBS 2008 server is up run the MIGRATION WIZARD  from the tasks screen
   
   1. Remove SBS2003 Group Policies and Login Scripts (if you have any).
   2. After the new SBS 2008 server is operational run the CONNECT TO THE INTERNET WIZARD
   3. Run the INTERNET ADDRESS MANAGEMENT WIZARD
   4. Manually set the DNS FORWARDERS
   5. Start the Exchange Migration
      
      1. Have users shut down Outlook
      2. Move mailboxes to the new Exchange server
      3. Move Offline Address Book
      4. Move Public Folders
      5. Remove Internet & POP3 connectors on old SBS 2003 Server
      6. When users restart Outlook they will be automatically reconfigured

       

3. Migrate file shares manually from the old server to the new using RoboCopy or XCopy.
   1. Personally I like RoboCopy which is built into Vista/7 and Server 2008/R2 using a command like
      1. robocopy \\old2003server\F$ F:\ /mir /xj /sec /r:1
      2. You can lookup all these switches by typing robocopy /? at a cmd prompt
         1. the most important switch is /sec (copy security i.e. permissions)
4. Migrate internal Web Site and DNS entry for it (if used), and fax (if used)

     

5. Migrate your Active Directory Security groups and you MUST assign a CREATED value to migrated AD Groups using Users & Computers or ADSIedit