diff --git a/src/main/java/org/jruby/ext/openssl/ASN1.java b/src/main/java/org/jruby/ext/openssl/ASN1.java
index 2444d9e9..37a109f4 100644
--- a/src/main/java/org/jruby/ext/openssl/ASN1.java
+++ b/src/main/java/org/jruby/ext/openssl/ASN1.java
@@ -1049,10 +1049,15 @@ else if ( obj instanceof ASN1GraphicString ) {
             if (taggedObj.getTagClass() == BERTags.APPLICATION) {
                 IRubyObject tag = runtime.newFixnum( taggedObj.getTagNo() );
                 IRubyObject tag_class = runtime.newSymbol("APPLICATION");
-                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);
+                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);
+                } 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);
+                }
             } else {
                 IRubyObject val = decodeObject(context, ASN1, taggedObj.getBaseObject());
                 IRubyObject tag = runtime.newFixnum( taggedObj.getTagNo() );
@@ -1380,12 +1385,13 @@ 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(), tag, ((ASN1Data) value).toASN1(context));
+            } else if (value instanceof RubyObject) {
+                return new DERTaggedObject(isExplicitTagging(), getTagClass(context), 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(), tag, ((ASN1Data) value).toASN1(context));
         }
 
         @JRubyMethod