I tested with Confluence server 6.3.x and Confluence Cloud and I was able to paste numbered lists into Outlook 2011 email messages from both. May I know more about the versions of Outlook and Confluence you all are using?
I noticed that if I use plain text in Word, or paste the numbered list into a plain text editor like TextMate it does strip the numbers. is it possible your Outlook is configured to use plain text?
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