diff --git a/pkg/osx/build_env.sh b/pkg/osx/build_env.sh
index b6542844e9..2e7e5fc9c2 100755
--- a/pkg/osx/build_env.sh
+++ b/pkg/osx/build_env.sh
@@ -199,8 +199,8 @@ sudo -H $MAKE install
 ############################################################################
 echo -n -e "\033]0;Build_Env: OpenSSL\007"
 
-PKGURL="http://openssl.org/source/openssl-1.0.2l.tar.gz"
-PKGDIR="openssl-1.0.2l"
+PKGURL="http://openssl.org/source/openssl-1.0.2p.tar.gz"
+PKGDIR="openssl-1.0.2p"
 
 download $PKGURL
 
@@ -241,7 +241,7 @@ sudo -H $MAKE install
 ############################################################################
 # upgrade pip
 ############################################################################
-sudo -H $PIP install --upgrade pip
+sudo -H $PIP install --upgrade pip --trusted-host pypi.org --trusted-host files.pythonhosted.org
 
 ############################################################################
 # Download and install salt python dependencies
diff --git a/pkg/osx/req.txt b/pkg/osx/req.txt
index f117545748..4897e4568b 100644
--- a/pkg/osx/req.txt
+++ b/pkg/osx/req.txt
@@ -25,7 +25,7 @@ PyYAML==3.12
 pyzmq==16.0.2
 requests==2.18.1
 singledispatch==3.4.0.3
-six==1.10.0
+six==1.11.0
 smmap==0.9.0
 timelib==0.2.4
 tornado==4.5.1
diff --git a/pkg/osx/shasums/openssl-1.0.2l.tar.gz.sha512 b/pkg/osx/shasums/openssl-1.0.2l.tar.gz.sha512
deleted file mode 100644
index 9dac0d205f..0000000000
--- a/pkg/osx/shasums/openssl-1.0.2l.tar.gz.sha512
+++ /dev/null
@@ -1 +0,0 @@
-047d964508ad6025c79caabd8965efd2416dc026a56183d0ef4de7a0a6769ce8e0b4608a3f8393d326f6d03b26a2b067e6e0c750f35b20be190e595e8290c0e3  ./openssl-1.0.2l.tar.gz
diff --git a/pkg/osx/shasums/openssl-1.0.2p.tar.gz.sha512 b/pkg/osx/shasums/openssl-1.0.2p.tar.gz.sha512
new file mode 100644
index 0000000000..11b018cfe7
--- /dev/null
+++ b/pkg/osx/shasums/openssl-1.0.2p.tar.gz.sha512
@@ -0,0 +1 @@
+958c5a7c3324bbdc8f07dfb13e11329d9a1b4452c07cf41fbd2d42b5fe29c95679332a3476d24c2dc2b88be16e4a24744aba675a05a388c0905756c77a8a2f16  ./openssl-1.0.2p.tar.gz