diff --git a/flake.nix b/flake.nix
index 217549e..23ba5f8 100644
--- a/flake.nix
+++ b/flake.nix
@@ -145,7 +145,18 @@
                   ruby -e 'puts "ok"' > $out
                 '';
               };
-            } // (lib.optionalAttrs (with import ./lib/version-comparison.nix rubyVersion; greaterOrEqualTo "2.2") {
+            } // (lib.optionalAttrs (with versionComparison rubyVersion; greaterOrEqualTo "2.4") {
+              # Ruby <2.4 only supports openssl 1.0 and not openssl1.1. openssl 1.0 is not supported by nixpkgs
+              # anymore, so we will not support it here.
+              "${rubyName}-openssl" = {
+                nativeBuildInputs = [
+                  ruby
+                ];
+                command = ''
+                  ruby -e 'require "openssl"; puts OpenSSL::OPENSSL_VERSION' > $out
+                '';
+              };
+            }) // (lib.optionalAttrs (with versionComparison rubyVersion; greaterOrEqualTo "2.2") {
               "${rubyName}-bundlerEnv" = let
                 gems = pkgs.bundlerEnv {
                   name = "gemset";
diff --git a/ruby/overrides.nix b/ruby/overrides.nix
index 2b1a393..09cf03c 100644
--- a/ruby/overrides.nix
+++ b/ruby/overrides.nix
@@ -24,7 +24,7 @@
   }
   {
     condition = version: with versionComparison version;
-      lessThan "3.0.3";
+      lessThan "3.1";
     override = pkg: pkg.override { openssl = openssl_1_1; };
   }
   {