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I understand you had it working on the XP Machine but I can't understand why you have 2 converters.
I have a similar set-up with only a USB to serial adaptor then I removed the serial connector and re-terminated it. What I can see is that your system is converting twice which may cause a problem.
Is any of the components you have used new in the latest set-up or all the same?
Personally the only thing the Shoestring would do is act as a gender change adaptor, but $41.00 is a bit pricey for a gender changer.
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