Windows might prompt to reactivate if it detects a significant hardware change, but an update of VMware tools shouldn't trigger that.
When you deploy from a template and sysprep, it will want to activate at that time as well. Windows 2008 gives you 3 days, I think, before it will force make you activate. Even if you activated your gold template, your new VM is a new insance of Windows, and it will want to activate it.
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IT Guy since 12/2000... Virtual since 10/2006...
VCAP-DCA #2222