diff --git a/.travis.yml b/.travis.yml
index 3deea542c..5d7cf6992 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -7,6 +7,7 @@ addons:
             - gcc-5
             - binutils-mingw-w64
             - gcc-mingw-w64
+            - wine
         sources:
             - llvm-toolchain-precise-3.6
             - ubuntu-toolchain-r-test
@@ -51,6 +52,10 @@ matrix:
           compiler: i686-w64-mingw32-gcc
         - os: osx
           compiler: x86_64-w64-mingw32-gcc
+        - compiler: i686-w64-mingw32-gcc
+          env: CONFIG_OPTS="shared"
+        - compiler: x86_64-w64-mingw32-gcc
+          env: CONFIG_OPTS="shared"
     allow_failures:
         - compiler: i686-w64-mingw32-gcc
           env: CONFIG_OPTS="--debug --strict-warnings"
@@ -70,7 +75,10 @@ before_script:
 
 script:
     - make
-    - if [ -z "$CROSS_COMPILE" ]; then make test; fi
+    - if [ -n "$CROSS_COMPILE" ]; then
+          export EXE_SHELL="wine" WINEPREFIX=`pwd`;
+      fi
+    - make test
 
 notifications:
     email:
diff --git a/Makefile.org b/Makefile.org
index 3ecc5c5a0..5aa721f27 100644
--- a/Makefile.org
+++ b/Makefile.org
@@ -437,7 +437,9 @@ test:   tests
 tests: rehash
 	@(cd test && echo "testing..." && \
 	$(CLEARENV) && $(MAKE) -e $(BUILDENV) TOP=.. TESTS='$(TESTS)' OPENSSL_DEBUG_MEMORY=on OPENSSL_CONF=../apps/openssl.cnf tests );
-	OPENSSL_CONF=apps/openssl.cnf util/opensslwrap.sh version -a
+	@if [ -z "$(CROSS_COMPILE)" ]; then \
+		OPENSSL_CONF=apps/openssl.cnf util/opensslwrap.sh version -a; \
+	fi
 
 list-tests:
 	@(cd test && \