If you have installed SP1 of WSS 3.0 or MOSS 2007, declarative workflows will not start if you log in as the system account. The fix is here:
http://kbalertz.com/947284/declarative-workflow-start-automatically-after-install-Windows-SharePoint-Services-Service.aspx
I would at least hope for an entry in the Event Log or SharePoint Hive log files rather than a silent failure in this case!
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