diff --git a/pkgs/top-level/python-packages.nix b/pkgs/top-level/python-packages.nix
index 31be94fd0226..ca1647f21c83 100644
--- a/pkgs/top-level/python-packages.nix
+++ b/pkgs/top-level/python-packages.nix
@@ -20325,16 +20325,26 @@ in modules // {
 
   pyopenssl = buildPythonPackage rec {
     name = "pyopenssl-${version}";
-    version = "16.0.0";
+    version = "16.1.0";
 
     src = pkgs.fetchurl {
       url = "mirror://pypi/p/pyOpenSSL/pyOpenSSL-${version}.tar.gz";
-      sha256 = "0zfijaxlq4vgi6jz0d4i5xq9ygqnyps6br7lmigjhqnh8gp10g9n";
+      sha256 = "88f7ada2a71daf2c78a4f139b19d57551b4c8be01f53a1cb5c86c2f3bf01355f";
     };
 
-    # 12 tests failing, 26 error out
-    doCheck = false;
+    preCheck = stdenv.lib.optionalString stdenv.isDarwin ''
+      sed -i 's/test_numeric_string_x509_name_entry/noop/' tests/hazmat/backends/test_openssl.py
+    '' + ''
+      sed -i 's/test_set_default_verify_paths/noop/' tests/test_ssl.py
+    '';
 
+    checkPhase = ''
+      runHook preCheck
+      export LANG="en_US.UTF-8";
+      py.test;
+      runHook postCheck'';
+
+    buildInputs = [ pkgs.openssl self.pytest pkgs.glibcLocales ];
     propagatedBuildInputs = [ self.cryptography self.pyasn1 self.idna ];
   };