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With latest version of libusb libusb-1.0.18, I successfully ran "./configure" on cygwin, and got a weird make error, see below;

make[1]: Entering directory `C:/cygwin/home/libusb-1.0.18/libusb'
  CC     libusb_1_0_la-core.lo
  CC     libusb_1_0_la-descriptor.lo
  CC     libusb_1_0_la-io.lo
  CC     libusb_1_0_la-strerror.lo
  CC     libusb_1_0_la-sync.lo
  CC     libusb_1_0_la-hotplug.lo
process_begin: CreateProcess(NULL, /usr/bin/mkdir -p os, ...) failed.
make (e=2): The system cannot find the file specified.
make[1]: *** [os/.dirstamp] Error 2
make[1]: Leaving directory `C:/cygwin/home/libusb-1.0.18/libusb'
make: *** [check-recursive] Error 1

Also libusb-compat-0.1.5 requires a previous version of libusb to be installed, and ask's for disks that don't exist?!#?

Any suggestions. Is this a broken library as far as "windows" compiling is concerned? I don't have linux installed yet..

That's not the latest. Latest is 1.0.19.

I'm not seeing any issues recompiling the latest libusb on cygwin.

pete@dusk /d/libusb-1.0.19
$ uname -srv
CYGWIN_NT-6.3-WOW64 1.7.29(0.272/5/3) 2014-04-07 13:44
pete@dusk /d/libusb-1.0.19
$ ./configure
checking for a BSD-compatible install... /usr/bin/install -c
checking whether build environment is sane... yes
checking for a thread-safe mkdir -p... /usr/bin/mkdir -p
checking for gawk... gawk
checking whether make sets $(MAKE)... yes
checking whether make supports nested variables... yes
checking whether to enable maintainer-specific portions of Makefiles... no
checking whether make supports nested variables... (cached) yes
checking for gcc... gcc
checking whether the C compiler works... yes
checking for C compiler default output file name... a.exe
checking for suffix of executables... .exe
checking whether we are cross compiling... no
checking for suffix of object files... o
checking whether we are using the GNU C compiler... yes
checking whether gcc accepts -g... yes
checking for gcc option to accept ISO C89... none needed
checking whether gcc understands -c and -o together... yes
checking for style of include used by make... GNU
checking dependency style of gcc... ./configure: line 3987: ./depcomp: Permission denied
checking build system type... i686-pc-cygwin
checking host system type... i686-pc-cygwin
checking how to print strings... printf
checking for a sed that does not truncate output... /usr/bin/sed
checking for grep that handles long lines and -e... /usr/bin/grep
checking for egrep... /usr/bin/grep -E
checking for fgrep... /usr/bin/grep -F
checking for ld used by gcc... /usr/i686-pc-cygwin/bin/ld.exe
checking if the linker (/usr/i686-pc-cygwin/bin/ld.exe) is GNU ld... yes
checking for BSD- or MS-compatible name lister (nm)... /usr/bin/nm -B
checking the name lister (/usr/bin/nm -B) interface... BSD nm
checking whether ln -s works... yes
checking the maximum length of command line arguments... 8192
checking whether the shell understands some XSI constructs... yes
checking whether the shell understands "+="... yes
checking how to convert i686-pc-cygwin file names to i686-pc-cygwin format... func_convert_file_noop
checking how to convert i686-pc-cygwin file names to toolchain format... func_convert_file_noop
checking for /usr/i686-pc-cygwin/bin/ld.exe option to reload object files... -r
checking for objdump... objdump
checking how to recognize dependent libraries... file_magic ^x86 archive import|^x86 DLL
checking for dlltool... dlltool
checking how to associate runtime and link libraries... func_cygming_dll_for_implib
checking for ar... ar
checking for archiver @FILE support... @
checking for strip... strip
checking for ranlib... ranlib
checking command to parse /usr/bin/nm -B output from gcc object... ok
checking for sysroot... no
checking for mt... mt
checking if mt is a manifest tool... yes
checking how to run the C preprocessor... gcc -E
checking for ANSI C header files... yes
checking for sys/types.h... yes
checking for sys/stat.h... yes
checking for stdlib.h... yes
checking for string.h... yes
checking for memory.h... yes
checking for strings.h... yes
checking for inttypes.h... yes
checking for stdint.h... yes
checking for unistd.h... yes
checking for dlfcn.h... yes
checking for objdir... .libs
checking if gcc supports -fno-rtti -fno-exceptions... no
checking for gcc option to produce PIC... -DDLL_EXPORT -DPIC
checking if gcc PIC flag -DDLL_EXPORT -DPIC works... yes
checking if gcc static flag -static works... yes
checking if gcc supports -c -o file.o... yes
checking if gcc supports -c -o file.o... (cached) yes
checking whether the gcc linker (/usr/i686-pc-cygwin/bin/ld.exe) supports shared libraries... yes
checking whether -lc should be explicitly linked in... yes
checking dynamic linker characteristics... Win32 ld.exe
checking how to hardcode library paths into programs... immediate
checking whether stripping libraries is possible... yes
checking if libtool supports shared libraries... yes
checking whether to build shared libraries... yes
checking whether to build static libraries... yes
checking for windres... windres
checking for inline... inline
checking operating system... Cygwin (using Windows backend)
checking sys/timerfd.h usability... no
checking sys/timerfd.h presence... no
checking for sys/timerfd.h... no
checking whether TFD_NONBLOCK is declared... no
checking whether to use timerfd for timing... no (header not available)
checking for struct timespec... yes
checking syslog.h usability... yes
checking syslog.h presence... yes
checking for syslog.h... yes
checking for syslog... yes
checking for sigaction... yes
checking sys/time.h usability... yes
checking sys/time.h presence... yes
checking for sys/time.h... yes
checking for gettimeofday... yes
checking signal.h usability... yes
checking signal.h presence... yes
checking for signal.h... yes
checking that generated files are newer than configure... done
configure: creating ./config.status
config.status: creating libusb-1.0.pc
config.status: creating Makefile
config.status: creating libusb/Makefile
config.status: creating examples/Makefile
config.status: creating tests/Makefile
config.status: creating doc/Makefile
config.status: creating doc/doxygen.cfg
config.status: creating config.h
config.status: executing depfiles commands
config.status: executing libtool commands
pete@dusk /d/libusb-1.0.19
$ make
make  all-recursive
make[1]: Entering directory '/d/libusb-1.0.19'
Making all in libusb
make[2]: Entering directory '/d/libusb-1.0.19/libusb'
  CC       libusb_1_0_la-core.lo
  CC       libusb_1_0_la-descriptor.lo
  CC       libusb_1_0_la-io.lo
  CC       libusb_1_0_la-strerror.lo
  CC       libusb_1_0_la-sync.lo
  CC       libusb_1_0_la-hotplug.lo
  CC       os/libusb_1_0_la-threads_posix.lo
  CC       os/libusb_1_0_la-poll_windows.lo
  CC       os/libusb_1_0_la-windows_usb.lo
  GEN      libusb-1.0.lo
  CCLD     libusb-1.0.la
make[2]: Leaving directory '/d/libusb-1.0.19/libusb'
Making all in doc
make[2]: Entering directory '/d/libusb-1.0.19/doc'
make[2]: Nothing to be done for 'all'.
make[2]: Leaving directory '/d/libusb-1.0.19/doc'
make[2]: Entering directory '/d/libusb-1.0.19'
make[2]: Leaving directory '/d/libusb-1.0.19'
make[1]: Leaving directory '/d/libusb-1.0.19'
pete@dusk /d/libusb-1.0.19

You may want to try upgrading or reinstalling cygwin.