diff --git a/src/main/java/org/jruby/ext/openssl/ASN1.java b/src/main/java/org/jruby/ext/openssl/ASN1.java
index 0dd7e337..f158642e 100644
--- a/src/main/java/org/jruby/ext/openssl/ASN1.java
+++ b/src/main/java/org/jruby/ext/openssl/ASN1.java
@@ -1063,15 +1063,14 @@ else if ( obj instanceof ASN1GraphicString ) {
                     break;
             }
 
-            if (taggedObj.getTagClass() == BERTags.APPLICATION) {
+            try {
                 final ASN1Sequence sequence = (ASN1Sequence) taggedObj.getBaseUniversal(false, SEQUENCE);
                 @SuppressWarnings("unchecked")
                 final RubyArray valArr = decodeObjects(context, ASN1, sequence.getObjects());
                 return ASN1.getClass("ASN1Data").newInstance(context, new IRubyObject[] { valArr, tag, tag_class }, Block.NULL_BLOCK);
-            } else {
-                IRubyObject val = decodeObject(context, ASN1, taggedObj.getBaseObject());
-                final RubyArray valArr = runtime.newArray(val);
-                return ASN1.getClass("ASN1Data").newInstance(context, new IRubyObject[] { valArr, tag, tag_class }, Block.NULL_BLOCK);
+            } catch (IllegalStateException e) {
+                IRubyObject val = decodeObject(context, ASN1, taggedObj.getBaseObject()).callMethod(context, "value");
+                return ASN1.getClass("ASN1Data").newInstance(context, new IRubyObject[] { val, tag, tag_class }, Block.NULL_BLOCK);
             }
         }
 
@@ -1397,12 +1396,13 @@ final ASN1TaggedObject toASN1TaggedObject(final ThreadContext context) {
                     vec.add( data );
                 }
                 return new DERTaggedObject(isExplicitTagging(), tag, new DERSequence(vec));
+            } else if (value instanceof ASN1Data) {
+                return new DERTaggedObject(isExplicitTagging(), tagClass, tag, ((ASN1Data) value).toASN1(context));
+            } else if (value instanceof RubyObject) {
+                return new DERTaggedObject(isExplicitTagging(), tagClass, tag, new DERGeneralString(value.asString().asJavaString()));
+            } else {
+                throw context.runtime.newTypeError("no implicit conversion of " + value.getMetaClass().getBaseName() + " into String");
             }
-
-            if (!(value instanceof ASN1Data)) {
-                throw new UnsupportedOperationException("toASN1 " + inspect() + " value: " + value.inspect() + " (" + value.getMetaClass() + ")");
-            }
-            return new DERTaggedObject(isExplicitTagging(), tagClass, tag, ((ASN1Data) value).toASN1(context));
         }
 
         @JRubyMethod
diff --git a/src/test/ruby/test_asn1.rb b/src/test/ruby/test_asn1.rb
index 9867a4b3..8e734196 100644
--- a/src/test/ruby/test_asn1.rb
+++ b/src/test/ruby/test_asn1.rb
@@ -251,6 +251,36 @@ def test_null
     }
   end
 
+  def test_encode_asn1_data
+    ai = OpenSSL::ASN1::ASN1Data.new(i = "bla", 0, :APPLICATION)
+    ai2 = OpenSSL::ASN1.decode(ai.to_der)
+    assert_equal :APPLICATION, ai2.tag_class
+    assert_equal 0, ai2.tag
+    assert_equal i, ai2.value
+
+    ai = OpenSSL::ASN1::ASN1Data.new(i = "bla", 4, :UNIVERSAL)
+    ai2 = OpenSSL::ASN1.decode(ai.to_der)
+    assert_equal :UNIVERSAL, ai2.tag_class
+    assert_equal 4, ai2.tag
+    assert_equal i, ai2.value
+
+    ai = OpenSSL::ASN1::ASN1Data.new(i = ["bla"], 0, :APPLICATION)
+    ai2 = OpenSSL::ASN1.decode(ai.to_der)
+    assert_equal :APPLICATION, ai2.tag_class
+    assert_equal 0, ai2.tag
+    assert_equal "bla", ai2.value
+
+    ai = OpenSSL::ASN1::ASN1Data.new(i = ["bla", "bla"], 0, :APPLICATION)
+    ai2 = OpenSSL::ASN1.decode(ai.to_der)
+    assert_equal :APPLICATION, ai2.tag_class
+    assert_equal 0, ai2.tag
+    assert_equal "blabla", ai2.value
+
+    assert_raise(ArgumentError) { OpenSSL::ASN1::ASN1Data.new(1).to_der }
+    assert_raise("no implicit conversion of Integer into String") { OpenSSL::ASN1::ASN1Data.new(1, 0, :APPLICATION).to_der }
+    assert_raise("no implicit conversion of Integer into String") { OpenSSL::ASN1::ASN1Data.new(1, 0, :CONTEXT_SPECIFIC).to_der }
+  end
+
   def test_encode_nil
     #Primitives raise TypeError, Constructives NoMethodError
 
@@ -1161,7 +1191,7 @@ def test_decode
   # This is from the upstream MRI tests, might be superseded by `test_bit_string_infinite_length`?
   def test_bitstring
     # TODO: Import Issue
-    # fails <nil> expected but was <0> 
+    # fails <nil> expected but was <0>
     #encode_decode_test B(%w{ 03 01 00 }), OpenSSL::ASN1::BitString.new(B(%w{}))
     # TODO: Import Issue
     # fails with <nil> expected but was <0>