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"...button which on click creates a pdf ..." How is that happening?
Hmmmm. It sounds like you're doing what we're doing for PDF generation, but I'm not sure what you mean by "flex window". Is this hitting a Java servlet? If you're clicking a Flex button "link" and sending data to a servlet using URLRequest, I do the same.
We haven't tested for 7+ attempts yet, that I know of. I will see if I can reproduce this myself. First (possibly stupid) thought that comes to mind is maybe connections are being left open. Are you closing the output stream? (assuming Java..) i.e.
What browser are you using?
Another possibility (if you're not using AlivePDF and you're generating the pdf server side) is that a reporting tool or other code you are using in the servlet is blowing up and trapping an exception it shouldn't be.
Or are you using the AlivePDF servlet trick with Flex side PDF generation?
Sorry, I'm unable to reproduce the same problem. We'll need more feedback.