Dependant files not Uploading to Server CS5

When I click "Yes" to upload dependant files to the server, DW doesn't upload them. For example, I added a downloadable PDF file to a page, saved it, clicked PUT to upload it to the server, and then when I went to the web and clicked on the link, I got the White Page File Not Found.
I have checked in my Site preferences, and my Site Manager and everything looks right, I'm not sure what I'm missing?
Thank you!

Sure, here is the page I worked on today. I added the very first link you see on the page, "Event Flyer"
http://www.slaalosangeles.org/events
Then I saved the page, and PUT the events.html, and the page uploaded correctly but is missing the PDF for the flyer. I intentionally didn't select it and upload it on its own because I wanted to test the dependent files feature.
Thanks for the help.

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