diff --git a/src/octoprint/__init__.py b/src/octoprint/__init__.py
index fb98ca0d..1ccdc835 100644
--- a/src/octoprint/__init__.py
+++ b/src/octoprint/__init__.py
@@ -21,6 +21,36 @@ del get_versions
 
 logging.basicConfig()
 
+#~~ try to ensure a sound SSL environment
+
+version_info = sys.version_info
+if version_info.major == 2 and version_info.minor <= 7 and version_info.micro < 9:
+	message = "Cannot configure PyOpenSSL for {} to ensure a secure " + \
+	          "SSL environment, update to Python >= 2.7.9 or install PyOpenSSL, see " + \
+	          "https://urllib3.readthedocs.org/en/latest/security.html#openssl-pyopenssl"
+
+	try:
+		# make sure our requests version of urllib3 is properly patched (if possible)
+		import requests.packages.urllib3.contrib.pyopenssl
+		requests.packages.urllib3.contrib.pyopenssl.inject_into_urllib3()
+	except ImportError:
+		logging.getLogger(__name__).warn(message.format("requests/urllib3"))
+
+	try:
+		import urllib3
+
+		# only proceed if urllib3 is even installed on its own
+		try:
+			# urllib3 is there, let's patch that too
+			import urllib3.contrib.pyopenssl
+			urllib3.contrib.pyopenssl.inject_into_urllib3()
+		except ImportError:
+			logging.getLogger(__name__).warn(message.format("urllib3"))
+	except ImportError:
+		pass
+
+del version_info
+
 #~~ init methods to bring up platform
 
 def init_platform(basedir, configfile, use_logging_file=True, logging_file=None,