Having managed a number of successful migrations, I've pieced together a number of resources I find invaluable. Starting from the top is MPECS Blog Post.
http://blog.mpecsinc.ca/2009/06/sbs-2003-to-sbs-2008-migration-guide.html
This is the official post, which is very comprehensive.
http://blogs.technet.com/b/sbs/archive/2009/02/19/sbs-2008-migrations-from-sbs-2003-keys-to-success.aspx
However, here are a couple of pointers to get you started:
· Your existing server needs to be as clean as possible and fully patched.
· Smarthosts will break the Exchange replication. The SBS BPA will flag this.
· Run the SBS BPA 2003 and ensure there are *no* issues.
· Run the Exchange BPA for a 2007 migration and ensure there are *no* issues.
· Ensure you have a backup *before* running the migration prep. You need this, if the migration fails, there is no rollback other than a restore.
· SBS 2008 is x64 only. You will have printer driver issues.
· Don’t create autodiscover DNS records, the migration will create a split DNS to handle this internally. Externally you need a SRV record, http://www.thirdtier.net/2009/02/setting-up-an-external-autodiscover-record-for-sbs-2008/
· A real certificate will save you pain. It doesn’t need to be a UC or SAN, just a real third party cert for remote.yourdomain.tld.
· You still have to manually move the data, applications.
· You only have *21 days* from when you start to complete the migration. After this the original box will reboot every hour.
· The old server must be completely removed, you can’t leave it to serve up apps once it’s dcpromo’d.
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