diff -ur openssl-1.0.2-stable-SNAP-20150106/config openssl-1.0.2-stable-SNAP-20150106-work/config
--- openssl-1.0.2-stable-SNAP-20150106/config	2014-06-10 23:00:03.000000000 +0100
+++ openssl-1.0.2-stable-SNAP-20150106-work/config	2015-01-06 10:33:45.129018700 +0000
@@ -344,7 +344,8 @@
 	echo "mips-sony-newsos4"; exit 0;
 	;;
 
-    MINGW*)
+    # MSYS identifies as "MINGW32_*"; MSYS2 identifies as "MSYS_*"
+    MSYS* | MINGW*)
 	echo "${MACHINE}-whatever-mingw"; exit 0;
 	;;
     CYGWIN*)
diff -ur openssl-1.0.2-stable-SNAP-20150106/Configure openssl-1.0.2-stable-SNAP-20150106-work/Configure
--- openssl-1.0.2-stable-SNAP-20150106/Configure	2015-01-05 14:00:47.000000000 +0000
+++ openssl-1.0.2-stable-SNAP-20150106-work/Configure	2015-01-06 10:35:47.851038000 +0000
@@ -550,6 +550,7 @@
 
 # MinGW
 "mingw", "gcc:-mno-cygwin -DL_ENDIAN -DWIN32_LEAN_AND_MEAN -fomit-frame-pointer -O3 -march=i486 -Wall::-D_MT:MINGW32:-lws2_32 -lgdi32 -lcrypt32:BN_LLONG ${x86_gcc_des} ${x86_gcc_opts} EXPORT_VAR_AS_FN:${x86_asm}:coff:win32:cygwin-shared:-D_WINDLL -DOPENSSL_USE_APPLINK:-mno-cygwin:.dll.a",
+"debug-mingw", "gcc:-DL_ENDIAN -DWIN32_LEAN_AND_MEAN -march=i486 -Wall -DBN_DEBUG -DREF_CHECK -DCONF_DEBUG -DBN_CTX_DEBUG -DCRYPTO_MDEBUG -g::-D_MT:MINGW32:-lws2_32 -lgdi32 -lcrypt32:BN_LLONG ${x86_gcc_des} ${x86_gcc_opts} EXPORT_VAR_AS_FN:${x86_asm}:coff:win32:cygwin-shared:-D_WINDLL -DOPENSSL_USE_APPLINK::.dll.a",
 # As for OPENSSL_USE_APPLINK. Applink makes it possible to use .dll
 # compiled with one compiler with application compiled with another
 # compiler. It's possible to engage Applink support in mingw64 build,
@@ -1144,7 +1145,7 @@
 
 my $IsMK1MF=scalar grep /^$target$/,@MK1MF_Builds;
 
-$exe_ext=".exe" if ($target eq "Cygwin" || $target eq "DJGPP" || $target =~ /^mingw/);
+$exe_ext=".exe" if ($target eq "Cygwin" || $target eq "DJGPP" || $target =~ /mingw/);
 $exe_ext=".nlm" if ($target =~ /netware/);
 $exe_ext=".pm"  if ($target =~ /vos/);
 $openssldir="/usr/local/ssl" if ($openssldir eq "" and $prefix eq "");
diff -ur openssl-1.0.2-stable-SNAP-20150106/Makefile.org openssl-1.0.2-stable-SNAP-20150106-work/Makefile.org
--- openssl-1.0.2-stable-SNAP-20150106/Makefile.org	2014-09-22 00:00:11.000000000 +0100
+++ openssl-1.0.2-stable-SNAP-20150106-work/Makefile.org	2015-01-06 10:36:53.560796300 +0000
@@ -582,7 +582,7 @@
 					chmod 555 $(INSTALL_PREFIX)$(INSTALLTOP)/$(LIBDIR)/$$i.new; \
 					mv -f $(INSTALL_PREFIX)$(INSTALLTOP)/$(LIBDIR)/$$i.new $(INSTALL_PREFIX)$(INSTALLTOP)/$(LIBDIR)/$$i; \
 				fi ); \
-				if expr $(PLATFORM) : 'mingw' > /dev/null; then \
+				if expr $(PLATFORM) : '.*mingw' > /dev/null; then \
 				(	case $$i in \
 						*crypto*) i=libeay32.dll;; \
 						*ssl*)    i=ssleay32.dll;; \
@@ -614,7 +614,7 @@
 install_html_docs:
 	here="`pwd`"; \
 	filecase=; \
-	case "$(PLATFORM)" in DJGPP|Cygwin*|mingw*|darwin*-*-cc) \
+	case "$(PLATFORM)" in DJGPP|Cygwin*|*mingw*|darwin*-*-cc) \
 		filecase=-i; \
 	esac; \
 	for subdir in apps crypto ssl; do \
@@ -645,7 +645,7 @@
 	@pod2man="`cd ./util; ./pod2mantest $(PERL)`"; \
 	here="`pwd`"; \
 	filecase=; \
-	case "$(PLATFORM)" in DJGPP|Cygwin*|mingw*|darwin*-*-cc) \
+	case "$(PLATFORM)" in DJGPP|Cygwin*|*mingw*|darwin*-*-cc) \
 		filecase=-i; \
 	esac; \
 	set -e; for i in doc/apps/*.pod; do \
diff -ur openssl-1.0.2-stable-SNAP-20150106/Makefile.shared openssl-1.0.2-stable-SNAP-20150106-work/Makefile.shared
--- openssl-1.0.2-stable-SNAP-20150106/Makefile.shared	2013-01-11 16:09:17.000000000 +0000
+++ openssl-1.0.2-stable-SNAP-20150106-work/Makefile.shared	2015-01-06 10:37:57.722466200 +0000
@@ -261,27 +261,32 @@
 	SHLIB=cyg$(LIBNAME); \
 	base=-Wl,--enable-auto-image-base; \
 	deffile=; \
-	if expr $(PLATFORM) : 'mingw' > /dev/null; then \
+	symbol_flag=-Wl,-s,-Bsymbolic; \
+	if expr $(PLATFORM) : '.*mingw' > /dev/null; then \
 		SHLIB=$(LIBNAME)eay32; base=; \
 		if test -f $(LIBNAME)eay32.def; then \
 			deffile=$(LIBNAME)eay32.def; \
 		fi; \
 	fi; \
+	if expr $(PLATFORM) : 'debug-mingw' > /dev/null; then \
+		symbol_flag=-Wl,-Bsymbolic; \
+	fi; \
 	SHLIB_SUFFIX=.dll; \
 	LIBVERSION="$(LIBVERSION)"; \
 	SHLIB_SOVER=${LIBVERSION:+"-$(LIBVERSION)"}; \
 	ALLSYMSFLAGS='-Wl,--whole-archive'; \
 	NOALLSYMSFLAGS='-Wl,--no-whole-archive'; \
-	SHAREDFLAGS="$(CFLAGS) $(SHARED_LDFLAGS) -shared $$base $$deffile -Wl,-s,-Bsymbolic"; \
+	SHAREDFLAGS="$(CFLAGS) $(SHARED_LDFLAGS) -shared $$base $$deffile $$symbol_flag"; \
 	$(LINK_SO_O)
 #for mingw target if def-file is in use dll-name should match library-name
 link_a.cygwin:
 	@ $(CALC_VERSIONS); \
 	INHIBIT_SYMLINKS=yes; \
 	SHLIB=cyg$(LIBNAME); SHLIB_SOVER=-$(LIBVERSION); SHLIB_SUFFIX=.dll; \
+	symbol_flag=-Wl,-s,-Bsymbolic; \
 	dll_name=$$SHLIB$$SHLIB_SOVER$$SHLIB_SUFFIX; extras=; \
 	base=-Wl,--enable-auto-image-base; \
-	if expr $(PLATFORM) : 'mingw' > /dev/null; then \
+	if expr $(PLATFORM) : '.*mingw' > /dev/null; then \
 		case $(LIBNAME) in \
 			crypto) SHLIB=libeay;; \
 			ssl) SHLIB=ssleay;; \
@@ -291,13 +296,16 @@
 		$(PERL) util/mkdef.pl 32 $$SHLIB > $$extras; \
 		base=; [ $(LIBNAME) = "crypto" ] && base=-Wl,--image-base,0x63000000; \
 	fi; \
+	if expr $(PLATFORM) : 'debug-mingw' > /dev/null; then \
+		symbol_flag=-Wl,-Bsymbolic; \
+	fi; \
 	dll_name=$$SHLIB$$SHLIB_SOVER$$SHLIB_SUFFIX; \
 	$(PERL) util/mkrc.pl $$dll_name | \
 		$(CROSS_COMPILE)windres -o rc.o; \
 	extras="$$extras rc.o"; \
 	ALLSYMSFLAGS='-Wl,--whole-archive'; \
 	NOALLSYMSFLAGS='-Wl,--no-whole-archive'; \
-	SHAREDFLAGS="$(CFLAGS) $(SHARED_LDFLAGS) -shared $$base -Wl,-s,-Bsymbolic -Wl,--out-implib,lib$(LIBNAME).dll.a $$extras"; \
+	SHAREDFLAGS="$(CFLAGS) $(SHARED_LDFLAGS) -shared $$base $$symbol_flag -Wl,--out-implib,lib$(LIBNAME).dll.a $$extras"; \
 	[ -f apps/$$dll_name ] && rm apps/$$dll_name; \
 	[ -f test/$$dll_name ] && rm test/$$dll_name; \
 	$(LINK_SO_A) || exit 1; \