diff --git a/Dockerfile b/Dockerfile
index b2ae0063c..fca5f9803 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -3,9 +3,11 @@ FROM debian:wheezy
 RUN set -ex; \
     apt-get update -qq; \
     apt-get install -y \
-        python \
-        python-pip \
-        python-dev \
+        gcc \
+        make \
+        zlib1g \
+        zlib1g-dev \
+        libssl-dev \
         git \
         apt-transport-https \
         ca-certificates \
@@ -15,6 +17,37 @@ RUN set -ex; \
     ; \
     rm -rf /var/lib/apt/lists/*
 
+# Build Python 2.7.9 from source
+RUN set -ex; \
+    curl -LO https://www.python.org/ftp/python/2.7.9/Python-2.7.9.tgz; \
+    tar -xzf Python-2.7.9.tgz; \
+    cd Python-2.7.9; \
+    ./configure --enable-shared; \
+    make; \
+    make install; \
+    cd ..; \
+    rm -rf /Python-2.7.9; \
+    rm Python-2.7.9.tgz
+
+# Make libpython findable
+ENV LD_LIBRARY_PATH /usr/local/lib
+
+# Install setuptools
+RUN set -ex; \
+    curl -LO https://bootstrap.pypa.io/ez_setup.py; \
+    python ez_setup.py; \
+    rm ez_setup.py
+
+# Install pip
+RUN set -ex; \
+    curl -LO https://pypi.python.org/packages/source/p/pip/pip-7.0.1.tar.gz; \
+    tar -xzf pip-7.0.1.tar.gz; \
+    cd pip-7.0.1; \
+    python setup.py install; \
+    cd ..; \
+    rm -rf pip-7.0.1; \
+    rm pip-7.0.1.tar.gz
+
 ENV ALL_DOCKER_VERSIONS 1.6.0
 
 RUN set -ex; \
diff --git a/compose/cli/utils.py b/compose/cli/utils.py
index 489b52e21..7f2ba2e0d 100644
--- a/compose/cli/utils.py
+++ b/compose/cli/utils.py
@@ -8,6 +8,7 @@ from docker import version as docker_py_version
 import os
 import platform
 import subprocess
+import ssl
 
 
 def yesno(prompt, default=None):
@@ -132,6 +133,7 @@ def get_version_info(scope):
     elif scope == 'full':
         return versioninfo + '\n' \
             + "docker-py version: %s\n" % docker_py_version \
-            + "%s version: %s" % (platform.python_implementation(), platform.python_version())
+            + "%s version: %s\n" % (platform.python_implementation(), platform.python_version()) \
+            + "OpenSSL version: %s" % ssl.OPENSSL_VERSION
     else:
         raise RuntimeError('passed unallowed value to `cli.utils.get_version_info`')
diff --git a/script/build-linux-inner b/script/build-linux-inner
index 34b0c06fd..adc030eaa 100755
--- a/script/build-linux-inner
+++ b/script/build-linux-inner
@@ -7,4 +7,4 @@ chmod 777 `pwd`/dist
 
 pyinstaller -F bin/docker-compose
 mv dist/docker-compose dist/docker-compose-Linux-x86_64
-dist/docker-compose-Linux-x86_64 --version
+dist/docker-compose-Linux-x86_64 version
diff --git a/script/build-osx b/script/build-osx
index 6ad00bcdb..2a9cf512e 100755
--- a/script/build-osx
+++ b/script/build-osx
@@ -1,5 +1,8 @@
 #!/bin/bash
 set -ex
+
+PATH="/usr/local/bin:$PATH"
+
 rm -rf venv
 virtualenv -p /usr/local/bin/python venv
 venv/bin/pip install -r requirements.txt
@@ -7,4 +10,4 @@ venv/bin/pip install -r requirements-dev.txt
 venv/bin/pip install .
 venv/bin/pyinstaller -F bin/docker-compose
 mv dist/docker-compose dist/docker-compose-Darwin-x86_64
-dist/docker-compose-Darwin-x86_64 --version
+dist/docker-compose-Darwin-x86_64 version
diff --git a/script/prepare-osx b/script/prepare-osx
index 69ac56f1c..ca2776b64 100755
--- a/script/prepare-osx
+++ b/script/prepare-osx
@@ -2,20 +2,51 @@
 
 set -ex
 
+python_version() {
+  python -V 2>&1
+}
+
+openssl_version() {
+  python -c "import ssl; print ssl.OPENSSL_VERSION"
+}
+
+desired_python_version="2.7.9"
+desired_python_brew_version="2.7.9"
+python_formula="https://raw.githubusercontent.com/Homebrew/homebrew/1681e193e4d91c9620c4901efd4458d9b6fcda8e/Library/Formula/python.rb"
+
+desired_openssl_version="1.0.1j"
+desired_openssl_brew_version="1.0.1j_1"
+openssl_formula="https://raw.githubusercontent.com/Homebrew/homebrew/62fc2a1a65e83ba9dbb30b2e0a2b7355831c714b/Library/Formula/openssl.rb"
+
+PATH="/usr/local/bin:$PATH"
+
 if !(which brew); then
   ruby -e "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install)"
 fi
 
 brew update
 
-if [ ! -f /usr/local/bin/python ]; then
-  brew install python
+if !(python_version | grep "$desired_python_version"); then
+  if brew list | grep python; then
+    brew unlink python
+  fi
+
+  brew install "$python_formula"
+  brew switch python "$desired_python_brew_version"
 fi
 
-if [ -n "$(brew outdated | grep python)" ]; then
-  brew upgrade python
+if !(openssl_version | grep "$desired_openssl_version"); then
+  if brew list | grep openssl; then
+    brew unlink openssl
+  fi
+
+  brew install "$openssl_formula"
+  brew switch openssl "$desired_openssl_brew_version"
 fi
 
+echo "*** Using $(python_version)"
+echo "*** Using $(openssl_version)"
+
 if !(which virtualenv); then
   pip install virtualenv
 fi