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The thing with the Dropbox internal folders is that Dropbox doesn't store its starred files as exact duplicates of the original file. So a starred PDF file on Dropbox isn't stored as a PDF file (although I haven't tried renaming it to see if it still works as a PDF).

I'd like to auto-save my PDF downloads to Dropbox so that when I annotate them, I'll be able to access them frictionlessly on my computer as well.

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The dropbox folder does not sync so what's the point? – Richard Borcsik Jun 10 '12 at 7:12
    
Actually it does sync. I know since I annotate the Dropbox PDFs I read on my tablet and I can see my annotations on my computer. – InquilineKea Jun 10 '12 at 7:34
    
Is this behavior documented somewhere? It doesn't work for me if I put a random file into the folder. – Richard Borcsik Jun 10 '12 at 8:11
    
@RichardBorcsik I get the same behavior if I open PDFs from the Android Dropbox App and annotate them. I think it's because the PDF was opened with Dropbox. If you just place a file within the Dropbox folder it won't get synced. – Flow Jun 10 '12 at 9:51
    
Yeah I use ezPDF – InquilineKea Jun 10 '12 at 18:43

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