Attached are patches, please address this issues, it is hard to keep sync this 
way.
The order of the issue is according to importance, (1, 2, 3) blockers.
Thanks!

1. _XOPEN_SOURCE cannot be used in mingw, strptime is never used anyway?

2. Make domd use cross compiler if available.

3. Update depend to execute update so that openssl/crypto/objects/obj_xref.h
will be generated as it is required for "make depend".

4. For some strange reason perl reports that symlinks are available
under msys, while it cannot create symbolic link when the to
is not reachable from cwd.

5. Added -DWIN32_LEAN_AND_MEAN and drop the conflict undef of x509.h

_XOPEN_SOURCE cannot be used in mingw, strptime is never used anyway?

Added -DWIN32_LEAN_AND_MEAN and drop the conflict undef of x509.h

Make domd use cross compiler if available.

Update depend to execute update so that openssl/crypto/objects/obj_xref.h
will be generated as it is required for "make depend".

---

diff -urNp openssl-SNAP-20081003.org/ssl/kssl.c openssl-SNAP-20081003/ssl/kssl.c
--- openssl-SNAP-20081003.org/ssl/kssl.c	2007-02-10 13:00:54.000000000 +0200
+++ openssl-SNAP-20081003/ssl/kssl.c	2008-10-04 21:30:51.000000000 +0300
@@ -68,7 +68,6 @@
 
 #include <openssl/opensslconf.h>
 
-#define _XOPEN_SOURCE 500 /* glibc2 needs this to declare strptime() */
 #include <time.h>
 #if 0 /* Experimental */
 #undef _XOPEN_SOURCE /* To avoid clashes with anything else... */
--- openssl-SNAP-20081019/Configure	2008-10-12 17:00:05.000000000 +0200
+++ openssl-SNAP-20081019.old/Configure	2008-10-21 20:13:28.000000000 +0200
@@ -495,7 +495,7 @@ my %table=(
 "BC-32","bcc32::::WIN32::BN_LLONG DES_PTR RC4_INDEX EXPORT_VAR_AS_FN:${no_asm}:win32",
 
 # MinGW
-"mingw", "gcc:-mno-cygwin -DL_ENDIAN -fomit-frame-pointer -O3 -march=i486 -Wall:::MINGW32:-lws2_32 -lgdi32:BN_LLONG ${x86_gcc_des} ${x86_gcc_opts} EXPORT_VAR_AS_FN:${x86_coff_asm}:win32:cygwin-shared:-D_WINDLL -DOPENSSL_USE_APPLINK:-mno-cygwin:.dll.a",
+"mingw", "gcc:-mno-cygwin -DWIN32_LEAN_AND_MEAN -DL_ENDIAN -fomit-frame-pointer -O3 -march=i486 -Wall:::MINGW32:-lws2_32 -lgdi32:BN_LLONG ${x86_gcc_des} ${x86_gcc_opts} EXPORT_VAR_AS_FN:${x86_coff_asm}:win32:cygwin-shared:-D_WINDLL -DOPENSSL_USE_APPLINK:-mno-cygwin:.dll.a",
 
 # UWIN 
 "UWIN", "cc:-DTERMIOS -DL_ENDIAN -O -Wall:::UWIN::BN_LLONG ${x86_gcc_des} ${x86_gcc_opts}:${no_asm}:win32",
@@ -1394,12 +1394,13 @@ while (<IN>)
 		s/^AR=\s*/AR= \$\(CROSS_COMPILE_PREFIX\)/;
 		s/^NM=\s*/NM= \$\(CROSS_COMPILE_PREFIX\)/;
 		s/^RANLIB=\s*/RANLIB= \$\(CROSS_COMPILE_PREFIX\)/;
+		s/^MAKEDEPPROG=.*$/MAKEDEPPROG= \$\(CROSS_COMPILE_PREFIX\)$cc/ if $cc eq "gcc";
 		}
 	else	{
 		s/^CC=.*$/CC= $cc/;
 		s/^RANLIB=.*/RANLIB= $ranlib/;
+		s/^MAKEDEPPROG=.*$/MAKEDEPPROG= $cc/ if $cc eq "gcc";
 		}
-	s/^MAKEDEPPROG=.*$/MAKEDEPPROG= $cc/ if $cc eq "gcc";
 	s/^CFLAG=.*$/CFLAG= $cflags/;
 	s/^DEPFLAG=.*$/DEPFLAG= $depflags/;
 	s/^PEX_LIBS=.*$/PEX_LIBS= $prelflags/;
--- openssl-SNAP-20081019/util/domd	2008-09-09 23:00:21.000000000 +0300
+++ openssl-SNAP-20081019.old/util/domd	2008-10-21 20:16:57.000000000 +0200
@@ -14,7 +14,7 @@ if [ "$MAKEDEPEND" = "" ]; then MAKEDEPE
 cp Makefile Makefile.save
 # fake the presence of Kerberos
 touch $TOP/krb5.h
-if [ "$MAKEDEPEND" = "gcc" ]; then
+if echo "$MAKEDEPEND" | grep "gcc" > /dev/null;  then
     args=""
     while [ $# -gt 0 ]; do
 	if [ "$1" != "--" ]; then args="$args $1"; fi
@@ -22,7 +22,7 @@ if [ "$MAKEDEPEND" = "gcc" ]; then
     done
     sed -e '/^# DO NOT DELETE.*/,$d' < Makefile > Makefile.tmp
     echo '# DO NOT DELETE THIS LINE -- make depend depends on it.' >> Makefile.tmp
-    gcc -Werror -D OPENSSL_DOING_MAKEDEPEND -M $args >> Makefile.tmp || exit
+    "$MAKEDEPEND" -Werror -D OPENSSL_DOING_MAKEDEPEND -M $args >> Makefile.tmp || exit
     ${PERL} $TOP/util/clean-depend.pl < Makefile.tmp > Makefile.new
     rm -f Makefile.tmp
 else
--- openssl-SNAP-20081019.old/Makefile.org	2008-06-04 15:00:10.000000000 +0300
+++ openssl-SNAP-20081019/Makefile.org	2008-10-21 20:30:17.000000000 +0200
@@ -409,7 +409,7 @@ tests: rehash
 report:
 	@$(PERL) util/selftest.pl
 
-depend:
+depend:	update
 	@set -e; target=depend; $(RECURSIVE_BUILD_CMD)
 
 lint:
--- openssl-SNAP-20081019/crypto/x509/x509.h	2008-10-08 01:00:18.000000000 +0200
+++ openssl-SNAP-20081019.new/crypto/x509/x509.h	2008-10-21 20:42:20.000000000 +0200
@@ -112,12 +112,6 @@
 extern "C" {
 #endif
 
-#ifdef OPENSSL_SYS_WIN32
-/* Under Win32 these are defined in wincrypt.h */
-#undef X509_NAME
-#undef X509_CERT_PAIR
-#endif
-
 #define X509_FILETYPE_PEM	1
 #define X509_FILETYPE_ASN1	2
 #define X509_FILETYPE_DEFAULT	3
For some strange reason perl reports that symlinks are available
under msys, while it cannot create symbolic link when the to
is not reachable from cwd.

---

diff -urNp openssl-SNAP-20080611.org/util/mklink.pl openssl-SNAP-20080611/util/mklink.pl
--- openssl-SNAP-20080611.org/util/mklink.pl	2006-02-09 15:00:35.000000000 +0200
+++ openssl-SNAP-20080611/util/mklink.pl	2008-06-13 12:42:06.000000000 +0300
@@ -51,6 +51,7 @@ my $to = join('/', @to_path);
 
 my $file;
 $symlink_exists=eval {symlink("",""); 1};
+if ($^O eq "msys") { $symlink_exists=0 };
 foreach $file (@files) {
     my $err = "";
     if ($symlink_exists) {

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