It seems that the length of the string passed to cygpath -w affects whether double quotes are translated or not:
$ cygpath -w '"12345"' | od -cAn " 1 2 3 4 5 " \n $ cygpath -w '"123456"' | od -cAn " 1 2 3 4 5 6 357 200 242 \n $ cygpath --version cygpath (cygwin) 2.5.2 Path Conversion Utility Copyright (C) 1998 - 2016 Cygwin Authors This is free software; see the source for copying conditions. There is NO warranty; not even for MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. $ uname -srv CYGWIN_NT-6.1 2.5.2(0.297/5/3) 2016-06-23 14:29 $ --Ken Nellis