Some Guesses:
Wrong Content Type sending text\html instead of application\pdf
Encrypted Java Script
Wrong Content Type sending text\html instead of application\pdf
Encrypted Java Script
I'd imagine that the redirects are at least part of the cause, as those aren't directly related to a user gesture. Clicking directly through to the download is "safer" in this context than clicking on something, and being redirected through a variety of trackers and dispatchers, as the user can't be expected to follow along.
The heuristic also takes into account whether you've been to a particular URL or domain before; that could also have an impact on certain files showing up as "safe" and others not.
Related Chrome Files:
http://code.google.com/searchframe#OAMlx_jo-ck/src/chrome/browser/download/download_util.cc
http://code.google.com/searchframe#OAMlx_jo-ck/src/chrome/browser/download/chrome_download_manager_delegate.cc&exact_package=chromium&q=ChromeDownloadManagerDelegate::IsDangerousFile.
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