"On the secure checkout page, why does the software not recognize images in my stylesheets"

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Short Answer:

Currently the shopping cart software cannot read external stylesheets (CSS files) when uploading your secure checkout design to our secure server.  It also cannot rewrite those URL's as it normally does for your HTML page.

Detailed Explanation:

This will be upgraded in a future version of the software.  This is like this because the shopping cart software was built long before CSS was popular.