diff --git a/scripts/bootstrap-ansible.sh b/scripts/bootstrap-ansible.sh
index ea4844a431..dfdc8cfcf6 100755
--- a/scripts/bootstrap-ansible.sh
+++ b/scripts/bootstrap-ansible.sh
@@ -70,20 +70,13 @@ case ${DISTRO_ID} in
     ubuntu)
         apt-get update
         DEBIAN_FRONTEND=noninteractive apt-get -y install \
-          git python-all python-dev curl python2.7-dev build-essential \
-          libssl-dev libffi-dev netcat python-requests python-openssl python-pyasn1 \
-          python-netaddr python-prettytable python-crypto python-yaml \
-          python-virtualenv
+          git python3-all python3-dev curl python3.5-dev build-essential \
+          libssl-dev libffi-dev netcat python3-requests python3-openssl python3-pyasn1 \
+          python3-netaddr python3-prettytable python3-crypto python3-yaml \
+          python3-virtualenv
         ;;
 esac
 
-# NOTE(mhayden): Ubuntu 16.04 needs python-ndg-httpsclient for SSL SNI support.
-#                This package is not needed in Ubuntu 14.04 and isn't available
-#                there as a package.
-if [[ "${DISTRO_ID}" == 'ubuntu' ]] && [[ "${DISTRO_VERSION_ID}" == '16.04' ]]; then
-  DEBIAN_FRONTEND=noninteractive apt-get -y install python-ndg-httpsclient
-fi
-
 # Install pip
 get_pip
 
@@ -96,7 +89,7 @@ elif [ -n "$HTTP_PROXY" ]; then
 fi
 
 # Figure out the version of python is being used
-PYTHON_EXEC_PATH="$(which python2 || which python)"
+PYTHON_EXEC_PATH="$(which python3 || which python2 || which python)"
 PYTHON_VERSION="$($PYTHON_EXEC_PATH -c 'import sys; print(".".join(map(str, sys.version_info[:3])))')"
 
 # Use https when Python with native SNI support is available
@@ -106,6 +99,12 @@ UPPER_CONSTRAINTS_PROTO=$([ "$PYTHON_VERSION" == $(echo -e "$PYTHON_VERSION\n2.7
 export UPPER_CONSTRAINTS_FILE=${UPPER_CONSTRAINTS_FILE:-"$UPPER_CONSTRAINTS_PROTO://git.openstack.org/cgit/openstack/requirements/plain/upper-constraints.txt?id=$(awk '/requirements_git_install_branch:/ {print $2}' playbooks/defaults/repo_packages/openstack_services.yml)"}
 
 # Create a Virtualenv for the Ansible runtime
+if [ -f "/opt/ansible-runtime/bin/python" ]; then
+  VENV_PYTHON_VERSION="$(/opt/ansible-runtime/bin/python -c 'import sys; print(".".join(map(str, sys.version_info[:3])))')"
+  if [ "$PYTHON_VERSION" != "$VENV_PYTHON_VERSION" ]; then
+    rm -rf /opt/ansible-runtime
+  fi
+fi
 virtualenv --clear ${VIRTUALENV_OPTIONS} --python="${PYTHON_EXEC_PATH}" /opt/ansible-runtime
 
 # The vars used to prepare the Ansible runtime venv
diff --git a/tests/roles/bootstrap-host/vars/ubuntu.yml b/tests/roles/bootstrap-host/vars/ubuntu.yml
index 916115e93a..324c22ee2b 100644
--- a/tests/roles/bootstrap-host/vars/ubuntu.yml
+++ b/tests/roles/bootstrap-host/vars/ubuntu.yml
@@ -23,7 +23,9 @@ packages_install:
   - linux-image-extra-{{ ansible_kernel }}
   - lvm2
   - python2.7
+  - python-crypto
   - python-dev
+  - python-yaml
   - sshpass
   - tmux
   - vim