diff --git a/src/main/java/org/jruby/ext/openssl/ASN1.java b/src/main/java/org/jruby/ext/openssl/ASN1.java
index fbe08bb9..79faf133 100644
--- a/src/main/java/org/jruby/ext/openssl/ASN1.java
+++ b/src/main/java/org/jruby/ext/openssl/ASN1.java
@@ -1935,6 +1935,10 @@ private ASN1EncodableVector toASN1EncodableVector(final ThreadContext context) {
                     if ( addEntry(context, vec, val.entry(i)) ) break;
                 }
             }
+            else if (respondsTo("to_der")) {
+                IRubyObject entry = value.callMethod(context, "to_der");
+                addEntry(context, vec, entry);
+            }
             else {
                 final int size = RubyInteger.num2int(value.callMethod(context, "size"));
                 for ( int i = 0; i < size; i++ ) {
diff --git a/src/test/ruby/test_asn1.rb b/src/test/ruby/test_asn1.rb
index 95f55137..da323f97 100644
--- a/src/test/ruby/test_asn1.rb
+++ b/src/test/ruby/test_asn1.rb
@@ -21,6 +21,18 @@ def test_encode_integer
     assert_equal i, OpenSSL::ASN1.decode(ai.to_der).value
   end
 
+  def test_encode_nested_sequence_to_der
+    data_sequence = ::OpenSSL::ASN1::Sequence([::OpenSSL::ASN1::Integer(0)])
+    asn1 = ::OpenSSL::ASN1::Sequence(data_sequence)
+    assert_equal "0\x03\x02\x01\x00", asn1.to_der
+  end
+
+  def test_encode_nested_set_to_der
+    data_set = ::OpenSSL::ASN1::Set([::OpenSSL::ASN1::Integer(0)])
+    asn1 = ::OpenSSL::ASN1::Set(data_set)
+    assert_equal "1\x03\x02\x01\x00", asn1.to_der
+  end
+
   def test_encode_nil
     #Primitives raise TypeError, Constructives NoMethodError