diff --git a/codegen/projections/rails_json/lib/rails_json/types.rb b/codegen/projections/rails_json/lib/rails_json/types.rb
index e2e0f443e..c3f783dc7 100644
--- a/codegen/projections/rails_json/lib/rails_json/types.rb
+++ b/codegen/projections/rails_json/lib/rails_json/types.rb
@@ -1925,50 +1925,30 @@ class StringValue < MyUnion
         def to_h
           { string_value: super(__getobj__) }
         end
-
-        def to_s
-          "#<RailsJson::Types::StringValue #{__getobj__ || 'nil'}>"
-        end
       end
 
       class BooleanValue < MyUnion
         def to_h
           { boolean_value: super(__getobj__) }
         end
-
-        def to_s
-          "#<RailsJson::Types::BooleanValue #{__getobj__ || 'nil'}>"
-        end
       end
 
       class NumberValue < MyUnion
         def to_h
           { number_value: super(__getobj__) }
         end
-
-        def to_s
-          "#<RailsJson::Types::NumberValue #{__getobj__ || 'nil'}>"
-        end
       end
 
       class BlobValue < MyUnion
         def to_h
           { blob_value: super(__getobj__) }
         end
-
-        def to_s
-          "#<RailsJson::Types::BlobValue #{__getobj__ || 'nil'}>"
-        end
       end
 
       class TimestampValue < MyUnion
         def to_h
           { timestamp_value: super(__getobj__) }
         end
-
-        def to_s
-          "#<RailsJson::Types::TimestampValue #{__getobj__ || 'nil'}>"
-        end
       end
 
       # Enum, one of: ["Foo", "Baz", "Bar", "1", "0"]
@@ -1976,50 +1956,30 @@ class EnumValue < MyUnion
         def to_h
           { enum_value: super(__getobj__) }
         end
-
-        def to_s
-          "#<RailsJson::Types::EnumValue #{__getobj__ || 'nil'}>"
-        end
       end
 
       class ListValue < MyUnion
         def to_h
           { list_value: super(__getobj__) }
         end
-
-        def to_s
-          "#<RailsJson::Types::ListValue #{__getobj__ || 'nil'}>"
-        end
       end
 
       class MapValue < MyUnion
         def to_h
           { map_value: super(__getobj__) }
         end
-
-        def to_s
-          "#<RailsJson::Types::MapValue #{__getobj__ || 'nil'}>"
-        end
       end
 
       class StructureValue < MyUnion
         def to_h
           { structure_value: super(__getobj__) }
         end
-
-        def to_s
-          "#<RailsJson::Types::StructureValue #{__getobj__ || 'nil'}>"
-        end
       end
 
       class RenamedStructureValue < MyUnion
         def to_h
           { renamed_structure_value: super(__getobj__) }
         end
-
-        def to_s
-          "#<RailsJson::Types::RenamedStructureValue #{__getobj__ || 'nil'}>"
-        end
       end
 
       class Unknown < MyUnion
@@ -2519,10 +2479,6 @@ class Quit < PlayerAction
         def to_h
           { quit: super(__getobj__) }
         end
-
-        def to_s
-          "#<RailsJson::Types::Quit #{__getobj__ || 'nil'}>"
-        end
       end
 
       class Unknown < PlayerAction
@@ -3424,10 +3380,6 @@ class Greeting < UnionPayload
         def to_h
           { greeting: super(__getobj__) }
         end
-
-        def to_s
-          "#<RailsJson::Types::Greeting #{__getobj__ || 'nil'}>"
-        end
       end
 
       class Unknown < UnionPayload
@@ -3450,30 +3402,18 @@ class Foo < UnionWithJsonName
         def to_h
           { foo: super(__getobj__) }
         end
-
-        def to_s
-          "#<RailsJson::Types::Foo #{__getobj__ || 'nil'}>"
-        end
       end
 
       class Bar < UnionWithJsonName
         def to_h
           { bar: super(__getobj__) }
         end
-
-        def to_s
-          "#<RailsJson::Types::Bar #{__getobj__ || 'nil'}>"
-        end
       end
 
       class Baz < UnionWithJsonName
         def to_h
           { baz: super(__getobj__) }
         end
-
-        def to_s
-          "#<RailsJson::Types::Baz #{__getobj__ || 'nil'}>"
-        end
       end
 
       class Unknown < UnionWithJsonName
diff --git a/codegen/projections/white_label/lib/white_label/types.rb b/codegen/projections/white_label/lib/white_label/types.rb
index 32a0c3967..bea8a9baa 100644
--- a/codegen/projections/white_label/lib/white_label/types.rb
+++ b/codegen/projections/white_label/lib/white_label/types.rb
@@ -175,26 +175,26 @@ class Defaults
       attr_accessor(*MEMBERS)
 
       def to_s
-        "#<WhiteLabel::Types::Defaults "\
-          "string=#{string || 'nil'}, "\
-          "struct=\"[SENSITIVE]\", "\
-          "un_required_number=#{un_required_number || 'nil'}, "\
-          "un_required_bool=#{un_required_bool || 'nil'}, "\
-          "number=#{number || 'nil'}, "\
-          "bool=#{bool || 'nil'}, "\
-          "hello=#{hello || 'nil'}, "\
-          "simple_enum=#{simple_enum || 'nil'}, "\
-          "valued_enum=#{valued_enum || 'nil'}, "\
-          "int_enum=#{int_enum || 'nil'}, "\
-          "null_document=#{null_document || 'nil'}, "\
-          "string_document=#{string_document || 'nil'}, "\
-          "boolean_document=#{boolean_document || 'nil'}, "\
-          "numbers_document=#{numbers_document || 'nil'}, "\
-          "list_document=#{list_document || 'nil'}, "\
-          "map_document=#{map_document || 'nil'}, "\
-          "list_of_strings=#{list_of_strings || 'nil'}, "\
-          "map_of_strings=#{map_of_strings || 'nil'}, "\
-          "iso8601_timestamp=#{iso8601_timestamp || 'nil'}, "\
+        '#<WhiteLabel::Types::Defaults ' \
+          "string=#{string || 'nil'}, " \
+          'struct=[SENSITIVE], ' \
+          "un_required_number=#{un_required_number || 'nil'}, " \
+          "un_required_bool=#{un_required_bool || 'nil'}, " \
+          "number=#{number || 'nil'}, " \
+          "bool=#{bool || 'nil'}, " \
+          "hello=#{hello || 'nil'}, " \
+          "simple_enum=#{simple_enum || 'nil'}, " \
+          "valued_enum=#{valued_enum || 'nil'}, " \
+          "int_enum=#{int_enum || 'nil'}, " \
+          "null_document=#{null_document || 'nil'}, " \
+          "string_document=#{string_document || 'nil'}, " \
+          "boolean_document=#{boolean_document || 'nil'}, " \
+          "numbers_document=#{numbers_document || 'nil'}, " \
+          "list_document=#{list_document || 'nil'}, " \
+          "map_document=#{map_document || 'nil'}, " \
+          "list_of_strings=#{list_of_strings || 'nil'}, " \
+          "map_of_strings=#{map_of_strings || 'nil'}, " \
+          "iso8601_timestamp=#{iso8601_timestamp || 'nil'}, " \
           "epoch_timestamp=#{epoch_timestamp || 'nil'}>"
       end
 
@@ -348,26 +348,26 @@ class DefaultsTestOutput
       attr_accessor(*MEMBERS)
 
       def to_s
-        "#<WhiteLabel::Types::DefaultsTestOutput "\
-          "string=#{string || 'nil'}, "\
-          "struct=\"[SENSITIVE]\", "\
-          "un_required_number=#{un_required_number || 'nil'}, "\
-          "un_required_bool=#{un_required_bool || 'nil'}, "\
-          "number=#{number || 'nil'}, "\
-          "bool=#{bool || 'nil'}, "\
-          "hello=#{hello || 'nil'}, "\
-          "simple_enum=#{simple_enum || 'nil'}, "\
-          "valued_enum=#{valued_enum || 'nil'}, "\
-          "int_enum=#{int_enum || 'nil'}, "\
-          "null_document=#{null_document || 'nil'}, "\
-          "string_document=#{string_document || 'nil'}, "\
-          "boolean_document=#{boolean_document || 'nil'}, "\
-          "numbers_document=#{numbers_document || 'nil'}, "\
-          "list_document=#{list_document || 'nil'}, "\
-          "map_document=#{map_document || 'nil'}, "\
-          "list_of_strings=#{list_of_strings || 'nil'}, "\
-          "map_of_strings=#{map_of_strings || 'nil'}, "\
-          "iso8601_timestamp=#{iso8601_timestamp || 'nil'}, "\
+        '#<WhiteLabel::Types::DefaultsTestOutput ' \
+          "string=#{string || 'nil'}, " \
+          'struct=[SENSITIVE], ' \
+          "un_required_number=#{un_required_number || 'nil'}, " \
+          "un_required_bool=#{un_required_bool || 'nil'}, " \
+          "number=#{number || 'nil'}, " \
+          "bool=#{bool || 'nil'}, " \
+          "hello=#{hello || 'nil'}, " \
+          "simple_enum=#{simple_enum || 'nil'}, " \
+          "valued_enum=#{valued_enum || 'nil'}, " \
+          "int_enum=#{int_enum || 'nil'}, " \
+          "null_document=#{null_document || 'nil'}, " \
+          "string_document=#{string_document || 'nil'}, " \
+          "boolean_document=#{boolean_document || 'nil'}, " \
+          "numbers_document=#{numbers_document || 'nil'}, " \
+          "list_document=#{list_document || 'nil'}, " \
+          "map_document=#{map_document || 'nil'}, " \
+          "list_of_strings=#{list_of_strings || 'nil'}, " \
+          "map_of_strings=#{map_of_strings || 'nil'}, " \
+          "iso8601_timestamp=#{iso8601_timestamp || 'nil'}, " \
           "epoch_timestamp=#{epoch_timestamp || 'nil'}>"
       end
 
@@ -631,17 +631,17 @@ class KitchenSinkInput
       attr_accessor(*MEMBERS)
 
       def to_s
-        "#<WhiteLabel::Types::KitchenSinkInput "\
-          "string=#{string || 'nil'}, "\
-          "simple_enum=#{simple_enum || 'nil'}, "\
-          "valued_enum=#{valued_enum || 'nil'}, "\
-          "struct=\"[SENSITIVE]\", "\
-          "document=#{document || 'nil'}, "\
-          "list_of_strings=#{list_of_strings || 'nil'}, "\
-          "list_of_structs=#{list_of_structs || 'nil'}, "\
-          "map_of_strings=#{map_of_strings || 'nil'}, "\
-          "map_of_structs=#{map_of_structs || 'nil'}, "\
-          "union=\"[SENSITIVE]\">"
+        '#<WhiteLabel::Types::KitchenSinkInput ' \
+          "string=#{string || 'nil'}, " \
+          "simple_enum=#{simple_enum || 'nil'}, " \
+          "valued_enum=#{valued_enum || 'nil'}, " \
+          'struct=[SENSITIVE], ' \
+          "document=#{document || 'nil'}, " \
+          "list_of_strings=#{list_of_strings || 'nil'}, " \
+          "list_of_structs=#{list_of_structs || 'nil'}, " \
+          "map_of_strings=#{map_of_strings || 'nil'}, " \
+          "map_of_structs=#{map_of_structs || 'nil'}, " \
+          'union=[SENSITIVE]>'
       end
     end
 
@@ -746,17 +746,17 @@ class KitchenSinkOutput
       attr_accessor(*MEMBERS)
 
       def to_s
-        "#<WhiteLabel::Types::KitchenSinkOutput "\
-          "string=#{string || 'nil'}, "\
-          "simple_enum=#{simple_enum || 'nil'}, "\
-          "valued_enum=#{valued_enum || 'nil'}, "\
-          "struct=\"[SENSITIVE]\", "\
-          "document=#{document || 'nil'}, "\
-          "list_of_strings=#{list_of_strings || 'nil'}, "\
-          "list_of_structs=#{list_of_structs || 'nil'}, "\
-          "map_of_strings=#{map_of_strings || 'nil'}, "\
-          "map_of_structs=#{map_of_structs || 'nil'}, "\
-          "union=\"[SENSITIVE]\">"
+        '#<WhiteLabel::Types::KitchenSinkOutput ' \
+          "string=#{string || 'nil'}, " \
+          "simple_enum=#{simple_enum || 'nil'}, " \
+          "valued_enum=#{valued_enum || 'nil'}, " \
+          'struct=[SENSITIVE], ' \
+          "document=#{document || 'nil'}, " \
+          "list_of_strings=#{list_of_strings || 'nil'}, " \
+          "list_of_structs=#{list_of_structs || 'nil'}, " \
+          "map_of_strings=#{map_of_strings || 'nil'}, " \
+          "map_of_structs=#{map_of_structs || 'nil'}, " \
+          'union=[SENSITIVE]>'
       end
     end
 
@@ -1170,10 +1170,6 @@ class String < Union
         def to_h
           { string: super(__getobj__) }
         end
-
-        def to_s
-          "#<WhiteLabel::Types::String #{__getobj__ || 'nil'}>"
-        end
       end
 
       # This docstring should be different than KitchenSink struct member.
diff --git a/codegen/smithy-ruby-codegen/src/main/java/software/amazon/smithy/ruby/codegen/generators/types/StructureGenerator.java b/codegen/smithy-ruby-codegen/src/main/java/software/amazon/smithy/ruby/codegen/generators/types/StructureGenerator.java
index eca3a953b..218c6ac80 100644
--- a/codegen/smithy-ruby-codegen/src/main/java/software/amazon/smithy/ruby/codegen/generators/types/StructureGenerator.java
+++ b/codegen/smithy-ruby-codegen/src/main/java/software/amazon/smithy/ruby/codegen/generators/types/StructureGenerator.java
@@ -191,25 +191,29 @@ private void renderToSMethod(RubyCodeWriter writer) {
 
             writer
                     .openBlock("\ndef to_s")
-                    .write("\"#<$L \"\\", fullQualifiedShapeName)
+                    .write("'#<$L ' \\", fullQualifiedShapeName)
                     .indent();
 
             while (iterator.hasNext()) {
                 MemberShape memberShape = iterator.next();
                 String key = symbolProvider.toMemberName(memberShape);
                 String value = "#{" + key + " || 'nil'}";
+                boolean memberLiteral = false;
 
                 if (memberShape.isBlobShape() || memberShape.isStringShape()) {
                     // Strings are wrapped in quotes
                     value = "\"" + value + "\"";
+                    memberLiteral = true;
                 } else if (memberShape.getMemberTrait(model, SensitiveTrait.class).isPresent()) {
-                    value = "\\\"[SENSITIVE]\\\"";
+                    value = "[SENSITIVE]";
+                    memberLiteral = true;
                 }
 
+                String quote = memberLiteral ? "'" : "\"";
                 if (iterator.hasNext()) {
-                    writer.write("\"$L=$L, \"\\", key, value);
+                    writer.write("$3L$1L=$2L, $3L \\", key, value, quote);
                 } else {
-                    writer.write("\"$L=$L>\"", key, value);
+                    writer.write("$3L$1L=$2L>$3L", key, value, quote);
                 }
             }
             writer
diff --git a/codegen/smithy-ruby-codegen/src/main/java/software/amazon/smithy/ruby/codegen/generators/types/UnionGenerator.java b/codegen/smithy-ruby-codegen/src/main/java/software/amazon/smithy/ruby/codegen/generators/types/UnionGenerator.java
index bda9accfa..df0bb69a8 100644
--- a/codegen/smithy-ruby-codegen/src/main/java/software/amazon/smithy/ruby/codegen/generators/types/UnionGenerator.java
+++ b/codegen/smithy-ruby-codegen/src/main/java/software/amazon/smithy/ruby/codegen/generators/types/UnionGenerator.java
@@ -112,19 +112,17 @@ public void render() {
     }
 
     private void renderUnionToSMethod(RubyCodeWriter writer, MemberShape memberShape) {
-        String fullQualifiedShapeName = settings.getModule() + "::Types::"
-                + symbolProvider.toMemberName(memberShape);
-
-        writer.write("")
-                .openBlock("def to_s");
-
-        if (memberShape.getMemberTrait(model, SensitiveTrait.class).isPresent()) {
-            writer.write("\"#<$L [SENSITIVE]>\"", fullQualifiedShapeName);
-        } else {
-            writer.write("\"#<$L #{__getobj__ || 'nil'}>\"", fullQualifiedShapeName);
+        if (!memberShape.getMemberTrait(model, SensitiveTrait.class).isPresent()) {
+            return;
         }
 
-        writer.closeBlock("end");
+        String fullQualifiedShapeName = settings.getModule() + "::Types::"
+                + symbolProvider.toMemberName(memberShape);
+        writer
+                .write("")
+                .openBlock("def to_s")
+                .write("\"#<$L [SENSITIVE]>\"", fullQualifiedShapeName)
+                .closeBlock("end");
     }
 
     private class UnionToHValueRbsVisitor extends ShapeVisitor.Default<String> {
diff --git a/hearth/lib/hearth/structure.rb b/hearth/lib/hearth/structure.rb
index 14702413a..22b685e7d 100644
--- a/hearth/lib/hearth/structure.rb
+++ b/hearth/lib/hearth/structure.rb
@@ -40,6 +40,23 @@ def to_h(obj = self)
     end
     alias to_hash to_h
 
+    # Returns a string representation of the Structure.
+    def to_s(obj = self)
+      case obj
+      when Union
+        "#<#{obj.class.name} #{obj.__getobj__ || 'nil'}>"
+      when Structure
+        _to_s_structure(obj)
+      when Hash
+        _to_s_hash(obj)
+      when Array
+        _to_s_array(obj)
+      else
+        obj.to_s
+      end
+    end
+    alias to_string to_s
+
     private
 
     def _to_h_structure(obj)
@@ -58,5 +75,23 @@ def _to_h_hash(obj)
     def _to_h_array(obj)
       obj.collect { |value| to_hash(value) }
     end
+
+    def _to_s_structure(obj)
+      members = obj.class::MEMBERS.map do |member|
+        value = to_string(obj.send(member))
+        " #{member}=#{value.empty? ? 'nil' : value}"
+      end
+      "#<#{self.class.name}#{members.join(',')}>"
+    end
+
+    def _to_s_hash(obj)
+      obj.transform_values do |value|
+        to_string(value)
+      end
+    end
+
+    def _to_s_array(obj)
+      obj.collect { |value| to_string(value) }
+    end
   end
 end
diff --git a/hearth/spec/hearth/structure_spec.rb b/hearth/spec/hearth/structure_spec.rb
index 518cb1a7e..e1a70e944 100644
--- a/hearth/spec/hearth/structure_spec.rb
+++ b/hearth/spec/hearth/structure_spec.rb
@@ -46,7 +46,7 @@ def _defaults
       end
     end
 
-    describe '#to_hash' do
+    describe '#to_h' do
       it 'serializes nested structs to a hash' do
         expected = {
           struct_value: { value: 'foo', default_value: 'default' },
@@ -65,5 +65,20 @@ def _defaults
         expect(subject.to_h).to eq expected
       end
     end
+
+    describe '#to_s' do
+      it 'returns a string representation of the structure' do
+        actual = subject.to_s
+        expect(actual).to include(subject.class.name)
+        expect(actual).to include(subject.struct_value.to_s)
+        expect(actual).to include(subject.array_value.first.to_s)
+        expect(actual).to include(subject.array_value.last.to_s)
+        expect(actual).to include(subject.hash_value[:key].to_s)
+        expect(actual).to include(subject.value)
+        expect(actual).to include(subject.union_value.to_s)
+        expect(actual).to include(subject.some_object.to_s)
+        expect(actual).to include(subject.default_value)
+      end
+    end
   end
 end
diff --git a/hearth/spec/hearth/union_spec.rb b/hearth/spec/hearth/union_spec.rb
index 862ff534f..5146fa66c 100644
--- a/hearth/spec/hearth/union_spec.rb
+++ b/hearth/spec/hearth/union_spec.rb
@@ -22,5 +22,12 @@ def to_h
         expect(subject.to_h).to eq(string_value: 'union')
       end
     end
+
+    describe '#to_s' do
+      it 'returns a string representation' do
+        expect(subject.to_s)
+          .to eq('#<Hearth::TestUnion::StringValue union>')
+      end
+    end
   end
 end