diff --git a/GNUmakefile b/GNUmakefile
index 0ea4456f..5493fd72 100644
--- a/GNUmakefile
+++ b/GNUmakefile
@@ -242,8 +242,8 @@ $(IOS_TARGETS): CFLAGS += -miphoneos-version-min=9.0 -Ideps/openssl/ios/ios64-xc
 $(IOS_TARGETS): LDFLAGS += -miphoneos-version-min=9.0 -Ldeps/openssl/ios/ios64-xcrun/usr/local/lib
 $(IOSSIM_TARGETS): CFLAGS += -Ideps/openssl/ios/iossimulator-xcrun/usr/local/include
 $(IOSSIM_TARGETS): LDFLAGS += -Ldeps/openssl/ios/iossimulator-xcrun/usr/local/lib
-$(LINUX_TARGETS): CFLAGS += -Ideps/openssl/$(UNAME_S)/$(UNAME_M)/usr/local/include
-$(LINUX_TARGETS): LDFLAGS += -Ldeps/openssl/$(UNAME_S)/$(UNAME_M)/usr/local/lib
+$(LINUX_TARGETS) $(MACOS_TARGETS): CFLAGS += -Ideps/openssl/$(UNAME_S)/$(UNAME_M)/usr/local/include
+$(LINUX_TARGETS) $(MACOS_TARGETS): LDFLAGS += -Ldeps/openssl/$(UNAME_S)/$(UNAME_M)/usr/local/lib
 
 ifeq ($(UNAME_M),x86_64)
 ifeq ($(UNAME_S),Linux)
@@ -1115,6 +1115,13 @@ $(LOCAL_DEPS):
 $(filter $(BUILD_DIR)/debug/%,$(APP_OBJS)) $(filter $(BUILD_DIR)/release/%,$(APP_OBJS)): | $(LOCAL_DEPS)
 endif
 
+ifeq ($(UNAME_S),Darwin)
+LOCAL_DEPS := deps/openssl/$(UNAME_S)/$(UNAME_M)/usr/local/lib/libssl.a
+$(LOCAL_DEPS):
+	+@tools/ssl-local
+$(filter $(BUILD_DIR)/macosdebug/%,$(APP_OBJS)) $(filter $(BUILD_DIR)/macosrelease/%,$(APP_OBJS)): | $(LOCAL_DEPS)
+endif
+
 ifeq ($(HAVE_WIN),1)
 WINDOWS_DEPS := deps/openssl/mingw64/usr/local/lib/libssl.a
 $(WINDOWS_DEPS):
diff --git a/tools/ssl-local b/tools/ssl-local
index 71d5effb..698f8475 100755
--- a/tools/ssl-local
+++ b/tools/ssl-local
@@ -7,7 +7,7 @@ BUILD_TARGET=$(uname -m)
 
 WORK_DIR=out/openssl-local
 rm -rf $WORK_DIR
-cp -arf deps/openssl_src/ $WORK_DIR
+cp -aRf deps/openssl_src/ $WORK_DIR
 
 echo "Building"
 pwd