Hi, Galgamesh,
Yes, Web Playlists automatically obfuscate the URLs in each playlist. By default, each user gets personalized URLs to the original media, and Web Playlists enforces that only the original requester can play those URLs.
For example, an entry in a typical Windows Media playlist (ASX file) might look like this:
<REF href="http://myserver.com/media/horton.wmv" mce_href="http://myserver.com/media/horton.wmv" />
In the playlist delivered by Web Playlists, the non-sharable tokenized entry would look like this:
<REF href="http://myserver.com/horton.isx?sessionId=b75a8dcd-618d-45c1-95bb-d37f389cb273;entryId=1" mce_href="http://myserver.com/horton.isx?sessionId=b75a8dcd-618d-45c1-95bb-d37f389cb273;entryId=1" />
If you choose to Disable Skip on your Web Playlists entries, you can also enforce a predetermined playback sequence.
Would this work for you?
-Chris