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We have tried to upgrade an Exchange 5.5 server to Exchange 2000 twice, running into trouble both times. This time we will try installing a fresh Exchange 2000 and migrate all settings from Exchange 5.5. Are there any special considerations we should keep in mind? Also, do you have any type of checklist for stuff like username shares and such?
There are several considerations when migrating from Exchange 5.5 to Exchange 2000; however, generally you don't need to worry about things like shares. Microsoft has documented the migration process in Knowledge Base article 316886, which you can find