diff --git a/pkgs/top-level/python-packages.nix b/pkgs/top-level/python-packages.nix
index e0a2d81374c..7653919790e 100644
--- a/pkgs/top-level/python-packages.nix
+++ b/pkgs/top-level/python-packages.nix
@@ -19684,11 +19684,11 @@ in modules // {
 
   pyopenssl = buildPythonPackage rec {
     name = "pyopenssl-${version}";
-    version = "0.15.1";
+    version = "16.0.0";
 
     src = pkgs.fetchurl {
       url = "mirror://pypi/p/pyOpenSSL/pyOpenSSL-${version}.tar.gz";
-      sha256 = "0wnnq15rhj7fhdcd8ycwiw6r6g3w9f9lcy6cigg8226vsrq618ph";
+      sha256 = "0zfijaxlq4vgi6jz0d4i5xq9ygqnyps6br7lmigjhqnh8gp10g9n";
     };
 
     # 12 tests failing, 26 error out
@@ -26556,7 +26556,8 @@ in modules // {
 
     postPatch = ''
       substituteInPlace requirements.txt \
-        --replace 'certifi==2015.11.20.1' 'certifi==2016.2.28'
+        --replace 'certifi==2015.11.20.1' 'certifi==2016.2.28' \
+        --replace 'pyopenssl==0.15.1' 'pyopenssl==16.0.0'
     '';
 
     propagatedBuildInputs = with self; [
@@ -27095,15 +27096,15 @@ in modules // {
 
   service-identity = buildPythonPackage rec {
     name = "service-identity-${version}";
-    version = "14.0.0";
+    version = "16.0.0";
 
     src = pkgs.fetchurl {
       url = "mirror://pypi/s/service_identity/service_identity-${version}.tar.gz";
-      sha256 = "0njg9bklkkp4rl2b9vsfh9aasxy3w2dmjkv9cq34jn65lwcs619i";
+      sha256 = "0dih7i7d36nbllcxgfkvbnaj1wlzhwfnpr4b97dz74czylif4c06";
     };
 
     propagatedBuildInputs = with self; [
-      characteristic pyasn1 pyasn1-modules pyopenssl idna
+      characteristic pyasn1 pyasn1-modules pyopenssl idna attrs
     ];
 
     buildInputs = with self; [