I've experienced this exact kind of problem. Turned out to be the LegacyExchangeDN attribute on the Exchange 2003 mailbox which has to match the object in Exchange 5.5. Also, Make sure that your new Windows AD account has an email address specified on the General tab.
Test email functionality...
You should have imposed mailbox limits when the Exchange server was first put in place. However, you can still put mailbox limits in place now. Every version of Exchange that I have used supports putting limits in place (Exchange 5.5 to 2003).
I suggest running mailbox manager to help you out...
Here are some tools you should have. There are some great ones here to use for replication and communication troubleshooting.
http://www.microsoft.com/downloads/details.aspx?FamilyID=9d467a69-57ff-4ae7-96ee-b18c4790cffd&displaylang=en
Your best bet is to put the ADC on a domain controller. Make sure you install the Exchange 2003 version of the ADC and make use of the Exchange 2003 deployment tools (much better than the tools provided by Exchange 2000).
The domain controller should be dedicated for this purpose (ADC).
How many people are affected? Do you have ANY Windows 98 clients with Outlook 2000 installed that DO work? Have you tried recreating the Outlook profile (this usually works)? Try installing Outlook 2002 or 2003, same problem?
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