---
# tasks file for python-requirements(On OSX)
# No task is needed.
- name: Install latest OpenSSL
  homebrew: name=openssl state=latest update_homebrew=yes
  register: result
# Note: http://www.task-notes.com/entry/20141130/1417275206
# force option is needed.
- name: Use OpenSSL of Homebrew instead of pre-installed one
  homebrew: name=openssl state=linked install_options="--force"
  when: "'Package upgraded' in result.msg"
- name: Install Python
  homebrew: name=python update_homebrew=yes

---
# tasks file for python-requirements(On OSX)
- name: Install Python
  homebrew: name=python update_homebrew=yes

Use pre-installed OpenSSL on OSX. (ex. LibreSSL)
Use pre-installed OpenSSL on OSX. (ex. LibreSSL)

OpenSSL Installation via Homebrew has several troubles now.
