gistfile1

APACHE_ROOT=C:\Program Files\Apache Software Foundation\Apache2.2
RUBY_ROOT=C:\Ruby
SRCS = \
    apache_cookie.c \
    apache_multipart_buffer.c \
    apache_request.c \
    apachelib.c \
    array_header.c \
    bucket.c \
    connection.c \
    cookie.c \
    error.c \
    mod_ruby.c \
    multival.c \
    paramtable.c \
    request.c \
    ruby_config.c \
    ruby_shared_stub.c \
    server.c \
    table.c \
    upload.c \
    uri.c

OBJS = $(SRCS:.c=.o)
CFLAGS=-I"$(APACHE_ROOT)\include" -I"$(RUBY_ROOT)\lib\ruby\1.8\i386-mswin32" -DWIN32
LDFLAGS=-L"$(APACHE_ROOT)\lib" -L"$(RUBY_ROOT)\lib"
LIBS= -llibapr-1.lib -llibaprutil-1.lib -llibhttpd.lib -lmsvcrt-ruby18.lib

.SUFFIXES: .c .o

all : mod_ruby.so

.c.o:
    gcc -c $(CFLAGS) -o $@ $<

mod_ruby.so : $(OBJS)
    gcc -shared -o $@ $(OBJS) $(LDFLAGS) $(LIBS)

clean : 
    -@rm -f *.o *.so

With these

LIBS= C:/Apache2.2/lib/libapr-1.lib C:/Apache2.2/lib/libaprutil-1.lib C:/Apache2.2/lib/libhttpd.lib -lmsvcrt-ruby18

I get the same error as above, that is a lot of "undefined reference to" errors. These must be connected to some linkage problem between the .o and the .c files.

i.e.: mod_ruby.o:mod_ruby.c:(.text+0xcf3): undefined reference to

Your nmake links against the DLL of Apache, correct? The DLLs of Apache on Windows are all placed in the bin Directory of Apache so I guess MinGW has to link against those DLLs.