diff --git a/include/prereq-build.mk b/include/prereq-build.mk
index 0e145c939b..42b624f817 100644
--- a/include/prereq-build.mk
+++ b/include/prereq-build.mk
@@ -71,10 +71,13 @@ $(eval $(call TestHostCommand,zlib, \
 	echo 'int main(int argc, char **argv) { gzdopen(0, "rb"); return 0; }' | \
 		gcc -include zlib.h -x c -o $(TMP_DIR)/a.out - $(zlib_link_flags)))
 
+# Xcode deprecated openssl, MacPorts doesn't work nicely for other packages
+ifneq ($(HOST_OS),Darwin)
 $(eval $(call TestHostCommand,libssl, \
 	Please install the openssl library (with development headers), \
 	echo 'int main(int argc, char **argv) { SSL_library_init(); return 0; }' | \
 		gcc $(HOST_CFLAGS) -include openssl/ssl.h -x c -o $(TMP_DIR)/a.out - -lcrypto -lssl $(HOST_LDFLAGS)))
+endif
 
 $(eval $(call TestHostCommand,perl-thread-queue, \
 	Please install the Perl Thread::Queue module, \
@@ -160,8 +163,10 @@ $(eval $(call SetupHostCommand,git,Please install Git (git-core) >= 1.7.12.2, \
 $(eval $(call SetupHostCommand,file,Please install the 'file' package, \
 	file --version 2>&1 | grep file))
 
+ifneq ($(HOST_OS),Darwin)
 $(eval $(call SetupHostCommand,openssl,Please install the 'openssl' utility, \
 	openssl version | grep '\(OpenSSL\|LibreSSL\)'))
+endif
 
 
 # Install ldconfig stub
diff --git a/tools/Makefile b/tools/Makefile
index 187655e7fd..690e13c0ae 100644
--- a/tools/Makefile
+++ b/tools/Makefile
@@ -77,6 +77,11 @@ $(curdir)/bc/compile := $(curdir)/bison/install
 $(curdir)/findutils/compile := $(curdir)/bison/install
 $(curdir)/gengetopt/compile := $(curdir)/libtool/install
 $(curdir)/patchelf/compile := $(curdir)/libtool/install
+ifeq ($(HOST_OS),Darwin)
+tools-y += libressl
+$(curdir)/mkimage/compile += $(curdir)/libressl/install
+$(curdir)/firmware-utils/compile += $(curdir)/libressl/install
+endif
 
 ifneq ($(CONFIG_CCACHE)$(CONFIG_SDK),)
 $(foreach tool, $(filter-out patch,$(tools-y)), $(eval $(curdir)/$(tool)/compile += $(curdir)/ccache/install))
diff --git a/tools/libressl/Makefile b/tools/libressl/Makefile
new file mode 100644
index 0000000000..bdf34d3138
--- /dev/null
+++ b/tools/libressl/Makefile
@@ -0,0 +1,22 @@
+#
+# Copyright (C) 2016 LEDE project
+#
+# This is free software, licensed under the GNU General Public License v2.
+# See /LICENSE for more information.
+#
+
+include $(TOPDIR)/rules.mk
+
+PKG_NAME:=libressl
+PKG_VERSION:=2.3.4
+PKG_MD5SUM:=b81d990b7eceb156df6eaa7e9f4a353e
+PKG_RELEASE:=1
+
+PKG_SOURCE:=$(PKG_NAME)-$(PKG_VERSION).tar.gz
+PKG_SOURCE_URL:=http://ftp.openbsd.org/pub/OpenBSD/LibreSSL/
+
+HOST_BUILD_PARALLEL:=1
+
+include $(INCLUDE_DIR)/host-build.mk
+
+$(eval $(call HostBuild))