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Okay after reading more thread i found how to open calibre in debug mode and tried converting it and looking at the txt file that result after closing calibre down I saw this here:
DeDRM v10.0.9: Failed to decrypt with error: No key found in 2 PIDs tried.
Thus I rechecked my serial in DeDRM and changed what I thought were "O" to "0" and now it is working so was user error on my end I guess.
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