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CRM 2011 Upgrade–Outlook Client Considerations
Here’s an excellent post that spells out everything you need to know:
http://blogs.msdn.com/b/crminthefield/archive/2011/03/16/ten-helpful-crm-outlook-2011-tips.aspx
Bottom line is: get your CRM 4 clients onto at least rollup 10 and then you are ok to upgrade the server to CRM 2011. Your CRM 4 clients will continue to function – even with offline data – and you can upgrade the clients at your leisure (with some constraints around going offline).
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