diff --git a/macosx/Makefile b/macosx/Makefile
index daff38cbe..9c50a1f02 100644
--- a/macosx/Makefile
+++ b/macosx/Makefile
@@ -29,7 +29,7 @@ NPING_STAGING_DIR = Nping
 NMAP_UPDATE_BUILD_DIR = nmap-update-build
 NMAP_UPDATE_STAGING_DIR = nmap-update
 
-MACPORTS_PREFIX=$(HOME)/macports-10.5
+MACPORTS_PREFIX=$(HOME)/macports-10.8
 PREFIX = /usr/local
 
 PACKAGEMAKER = /Developer/usr/bin/packagemaker
@@ -49,10 +49,10 @@ UNIVERSAL_CXX = g++
 # turn uses the arch value to decide which of its bootstrappers to
 # install.
 UNIVERSAL_ARCHFLAGS = -arch i386
-UNIVERSAL_CPPFLAGS = -isysroot /Developer/SDKs/MacOSX10.5.sdk
-UNIVERSAL_CFLAGS = $(UNIVERSAL_CPPFLAGS) -mmacosx-version-min=10.5 $(UNIVERSAL_ARCHFLAGS)
+UNIVERSAL_CPPFLAGS = -isysroot /Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.9.sdk
+UNIVERSAL_CFLAGS = $(UNIVERSAL_CPPFLAGS) -mmacosx-version-min=10.8 $(UNIVERSAL_ARCHFLAGS)
 UNIVERSAL_CXXFLAGS = $(UNIVERSAL_CFLAGS)
-UNIVERSAL_LDFLAGS = -Wl,-syslibroot,/Developer/SDKs/MacOSX10.5.sdk -mmacosx-version-min=10.5 $(UNIVERSAL_ARCHFLAGS)
+UNIVERSAL_LDFLAGS = -Wl,-syslibroot,/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.9.sdk -mmacosx-version-min=10.8 $(UNIVERSAL_ARCHFLAGS)
 
 CC = $(UNIVERSAL_CC)
 CXX = $(UNIVERSAL_CXX)
@@ -63,7 +63,9 @@ CFLAGS += $(UNIVERSAL_CFLAGS)
 CXXFLAGS += $(UNIVERSAL_CXXFLAGS)
 LDFLAGS += $(UNIVERSAL_LDFLAGS)
 
-PYTHON = /usr/bin/python
+PYTHON = $(MACPORTS_PREFIX)/bin/python2.7
+SVN_STATIC = $(MACPORTS_PREFIX)/lib/libsvn_subr-1.a $(MACPORTS_PREFIX)/lib/libsvn_client-1.a $(MACPORTS_PREFIX)/lib/libapr-1.a
+OPENSSL_STATIC = $(MACPORTS_PREFIX)/lib/libssl.a $(MACPORTS_PREFIX)/lib/libcrypto.a $(MACPORTS_PREFIX)/lib/libz.a
 
 $(IMAGE_NAME): $(IMAGE_STAGING_DIR)/$(PKG_NAME)
 	rm -f $@
@@ -77,32 +79,29 @@ $(IMAGE_STAGING_DIR)/$(PKG_NAME): stage-nmap stage-ncat stage-ndiff stage-zenmap
 export-%:
 	rm -rf $*
 # Using @BASE discards local changes.
-	svn export ..@BASE $*
+	svn export .. $*
 
 stage-nmap: export-$(NMAP_BUILD_DIR)
 	cd $(NMAP_BUILD_DIR) && ./configure --without-zenmap --without-ncat --without-ndiff --without-nping --without-nmap-update --with-openssl="$(MACPORTS_PREFIX)" $(CONFIGURE_ARGS)
-	make -C $(NMAP_BUILD_DIR) OPENSSL_LIBS="$(MACPORTS_PREFIX)/lib/libssl.a $(MACPORTS_PREFIX)/lib/libcrypto.a $(MACPORTS_PREFIX)/lib/libz.a"
+	make -C $(NMAP_BUILD_DIR) OPENSSL_LIBS="$(OPENSSL_STATIC)"
 	rm -rf $(NMAP_STAGING_DIR)
 	make -C $(NMAP_BUILD_DIR) install DESTDIR="`pwd`/$(NMAP_STAGING_DIR)"
 
 stage-ncat: export-$(NCAT_BUILD_DIR)
 	cd $(NCAT_BUILD_DIR) && ./configure --without-zenmap --with-ncat --without-ndiff --without-nping --without-nmap-update --with-openssl="$(MACPORTS_PREFIX)" $(CONFIGURE_ARGS)
-	make -C $(NCAT_BUILD_DIR) OPENSSL_LIBS="$(MACPORTS_PREFIX)/lib/libssl.a $(MACPORTS_PREFIX)/lib/libcrypto.a $(MACPORTS_PREFIX)/lib/libz.a"
+	make -d -C $(NCAT_BUILD_DIR) ncat_build OPENSSL_LIBS="$(OPENSSL_STATIC)"
 	rm -rf $(NCAT_STAGING_DIR)
-	make -C $(NCAT_BUILD_DIR) install-ncat DESTDIR="`pwd`/$(NCAT_STAGING_DIR)"
+	make -d -C $(NCAT_BUILD_DIR) install-ncat DESTDIR="`pwd`/$(NCAT_STAGING_DIR)"
 
 stage-nping: export-$(NPING_BUILD_DIR)
-# Link against the local MacPorts openssl because the 10.4u SDK doesn't
-# have EVP_sha256, used by Nping. We let configure find the libraries
-# dynamically, then link with the static libraries with "make".
 	cd $(NPING_BUILD_DIR) && ./configure --without-zenmap --without-ncat --without-ndiff --with-nping --without-nmap-update --with-openssl="$(MACPORTS_PREFIX)" $(CONFIGURE_ARGS)
-	make -C $(NPING_BUILD_DIR) OPENSSL_LIBS="$(MACPORTS_PREFIX)/lib/libssl.a $(MACPORTS_PREFIX)/lib/libcrypto.a $(MACPORTS_PREFIX)/lib/libz.a"
+	make -C $(NPING_BUILD_DIR) build-nping OPENSSL_LIBS="$(OPENSSL_STATIC)"
 	rm -rf $(NPING_STAGING_DIR)
 	make -C $(NPING_BUILD_DIR) install-nping DESTDIR="`pwd`/$(NPING_STAGING_DIR)"
 
 stage-nmap-update: export-$(NMAP_UPDATE_BUILD_DIR)
 	cd $(NMAP_UPDATE_BUILD_DIR) && ./configure --without-zenmap --without-ncat --without-ndiff --without-nping --with-nmap-update --with-apr=$(MACPORTS_PREFIX) --with-subversion=$(MACPORTS_PREFIX) --with-openssl="$(MACPORTS_PREFIX)" $(CONFIGURE_ARGS)
-	make -C $(NMAP_UPDATE_BUILD_DIR) OPENSSL_LIBS="$(MACPORTS_PREFIX)/lib/libssl.a $(MACPORTS_PREFIX)/lib/libcrypto.a $(MACPORTS_PREFIX)/lib/libz.a"
+	make -C $(NMAP_UPDATE_BUILD_DIR) build-nmap-update OPENSSL_LIBS="$(OPENSSL_STATIC)"
 	rm -rf $(NMAP_UPDATE_STAGING_DIR)
 	make -C $(NMAP_UPDATE_BUILD_DIR) install-nmap-update DESTDIR="`pwd`/$(NMAP_UPDATE_STAGING_DIR)"
 
diff --git a/macosx/README b/macosx/README
index 89d974c4a..3d2b92dad 100644
--- a/macosx/README
+++ b/macosx/README
@@ -1,6 +1,6 @@
 Nmap is a free and open source utility for network exploration and security auditing. Zenmap is a multi-platform graphical frontend and results viewer for Nmap. Ncat is a general-purpose network sending and receiving utility, a reimplementation of Netcat. Ndiff is a an Nmap scan comparison utility. Nping is a tool for packet generation and sending.
 
-This package contains Nmap, Zenmap, Ncat, Ndiff, and Nping. It is intended to work on Intel Macs running Mac OS X 10.6 or later.
+This package contains Nmap, Zenmap, Ncat, Ndiff, and Nping. It is intended to work on Intel Macs running Mac OS X 10.8 or later.
 
 Installation of all packages is optional. Unselect Zenmap to get just the command-line tool. Unselect Nmap if you prefer to use a copy of Nmap that is already installed. Zenmap will not work without Nmap.
 
diff --git a/zenmap/install_scripts/macosx/README b/zenmap/install_scripts/macosx/README
index e08292bb1..1833eb081 100644
--- a/zenmap/install_scripts/macosx/README
+++ b/zenmap/install_scripts/macosx/README
@@ -40,14 +40,14 @@ The following instructions show how to make a 10.5-compatible
 environment suitable for building Zenmap packages. It will be a separate
 installation in $HOME/macports-10.5 that won't interfere with your
 normal MacPorts installation in /opt/local. These instructions were done
-with MacPorts 2.0.3 on Mac OS X 10.6.8.
+with MacPorts 2.3.3 on Mac OS X 10.9.5.
 
 1. Install MacPorts.
 	export PATH=/usr/bin:/bin:/usr/sbin:/sbin
-	export PREFIX=$HOME/macports-10.5
-	tar xzvf MacPorts-2.1.1.tar.gz
-	cd MacPorts-2.1.1
-	./configure --with-no-root-privileges --prefix=$PREFIX --with-tclpackage=$PREFIX/Library/Tcl --with-applications-dir=$PREFIX/Applications
+	export PREFIX=$HOME/macports-10.8
+	tar xzvf MacPorts-2.3.3.tar.gz
+	cd MacPorts-2.3.3
+	./configure --with-no-root-privileges --prefix=$PREFIX --with-applications-dir=$PREFIX/Applications
 	make
 	make install
 2. Update the ports tree.
@@ -56,7 +56,7 @@ with MacPorts 2.0.3 on Mac OS X 10.6.8.
    Uncomment the line
 	build_arch			i386
    Add this line at the bottom:
-	macosx_deployment_target	10.5
+	macosx_deployment_target	10.8
 4. Make a local patched ports tree.
 	cd $PREFIX
 	mkdir ports
@@ -71,14 +71,14 @@ with MacPorts 2.0.3 on Mac OS X 10.6.8.
 	$PREFIX/bin/portindex
 6. Edit the file $PREFIX/etc/macports/sources.conf.
    Add a line
-	file:///Users/user/macports-10.5/ports
+	file:///Users/user/macports-10.8/ports
    above the rsync line. (Replace "user" with your user name.)
 7. Install the dependencies of Zenmap.
 	$PREFIX/bin/port install py26-pygtk py26-py2app apr apr-util
 
 Here are instructions for updating the patch to keep up with MacPorts
 changes. First, sync the original ports tree.
-	$PREFIX/bin/port sync
+	$PREFIX/bin/port selfupdate -v
 Restore a pristine partial ports tree:
 	cd $PREFIX
 	rsync -rv --existing --delete --exclude=PortIndex ports.orig/ ports/
diff --git a/zenmap/install_scripts/macosx/make-bundle.sh b/zenmap/install_scripts/macosx/make-bundle.sh
index 12474b2de..87aee8fde 100755
--- a/zenmap/install_scripts/macosx/make-bundle.sh
+++ b/zenmap/install_scripts/macosx/make-bundle.sh
@@ -25,8 +25,8 @@
 # environment. You need to have installed the packages py26-gtk and
 # py26-py2app.
 
-LIBPREFIX=$HOME/macports-10.5
-PYTHON=$LIBPREFIX/bin/python2.6
+LIBPREFIX=$HOME/macports-10.8
+PYTHON=$LIBPREFIX/bin/python2.7
 PKG_CONFIG=$LIBPREFIX/bin/pkg-config
 APP_NAME=Zenmap
 BASE=dist/$APP_NAME.app/Contents