diff --git a/lib/resource_registry.rb b/lib/resource_registry.rb
index 6f0a5286..10e0ed75 100644
--- a/lib/resource_registry.rb
+++ b/lib/resource_registry.rb
@@ -1,12 +1,13 @@
 require 'dry/transaction'
 require 'dry/transaction/operation'
+require 'dry/monads/result'
 require 'system/boot'
 require 'resource_registry/error'
 require 'resource_registry/types'
 require 'resource_registry/entities'
 require 'resource_registry/services'
 require 'resource_registry/stores'
-require 'resource_registry/validations'
+require File.expand_path(File.join(File.dirname(__FILE__), 'resource_registry/validations'))
 require 'resource_registry/registries'
 require 'resource_registry/serializers'
 require 'resource_registry/version'
@@ -26,8 +27,11 @@ def configure
     end
 
     def load_options(dir)
-      Dir.glob(File.join(dir, "*")).each do |file_path|
-        ResourceRegistry::Services::LoadRegistryOptions.new.call(file_path)
+      files_to_load = Dir.glob(File.join(dir, "*")).to_a
+      files_to_load.inject(Dry::Monads::Success(:ok)) do |result, file_path|
+        result.bind do |_ignore|
+          ResourceRegistry::Services::LoadRegistryOptions.new.call(file_path)
+        end
       end
     end
 
diff --git a/lib/resource_registry/entities.rb b/lib/resource_registry/entities.rb
index ef191bb4..f834503e 100644
--- a/lib/resource_registry/entities.rb
+++ b/lib/resource_registry/entities.rb
@@ -1,8 +1,4 @@
 require 'dry-struct' unless defined?(Dry::Struct)
-require 'resource_registry/types'
-require 'resource_registry/entities/dry_struct_setters'
-require 'resource_registry/entities/setting'
-require 'resource_registry/entities/option'
 require 'resource_registry/entities/registry'
 require 'resource_registry/entities/core_options'
 require 'resource_registry/entities/qualifying_life_event'
diff --git a/lib/resource_registry/entities/option.rb b/lib/resource_registry/entities/option.rb
index c398021d..249d9a87 100644
--- a/lib/resource_registry/entities/option.rb
+++ b/lib/resource_registry/entities/option.rb
@@ -1,19 +1,28 @@
+require 'resource_registry/entities/setting'
+
 module ResourceRegistry
   module Entities
-    class Option  < Dry::Struct
-      include Enumerable
-      include DryStructSetters
-
-      transform_keys(&:to_sym)
+    OptionConstructor = Types.Constructor("Option") { |val| Option.new(val) rescue nil }
 
-      # attribute :parent_namespace?, Types::Symbol
-      attribute :namespace?,   Types::Symbol
-      attribute :key,          Types::Symbol
+    class Option
+      extend Dry::Initializer
+      include Enumerable
+      option :namespace,   type: Dry::Types["coercible.symbol"], optional: true
+      option :key,          type: Dry::Types["coercible.symbol"], optional: true
 
       # TODO: Make settings attribute dynamically typed
-      attribute :settings?,   Types::Array.of(ResourceRegistry::Entities::Setting)
-      attribute :namespaces?, Types::Array.of(ResourceRegistry::Entities::Option)
+      option :settings, type: Dry::Types['coercible.array'].of(SettingConstructor), optional: true, default: -> { [] }
+      option :namespaces, Dry::Types['coercible.array'].of(OptionConstructor), optional: true, default: -> { [] }
+
+      def each
+        settings.each do |s|
+          yield s
+        end
 
+       namespaces.each do |ns|
+          yield ns
+        end
+      end
     end
   end
 end
\ No newline at end of file
diff --git a/lib/resource_registry/entities/registry.rb b/lib/resource_registry/entities/registry.rb
index b91873c6..dfbce8b5 100644
--- a/lib/resource_registry/entities/registry.rb
+++ b/lib/resource_registry/entities/registry.rb
@@ -1,8 +1,14 @@
+require 'resource_registry/entities/option'
+
 module ResourceRegistry
   module Entities
     class Registry < Dry::Struct
 
       # Configuration values
+      # Only let this be defined once, dry autoloading will
+      # try to continue loading this file and give us conflict
+      # issues.
+      unless defined?(Config)
       attribute :config do
         attribute :name,              Types::Strict::String
         attribute :root,              Types::Strict::String
@@ -15,7 +21,7 @@ class Registry < Dry::Struct
         # Dir, plus optional custom auto_register block
         attribute :auto_register,     Types::Array.of(Types::NilOrString) #| Types::Undefined
       end
-
+      
       attribute :timestamp,           Types::DateTime.default { DateTime.now }
 
       # Persistence values
@@ -26,8 +32,8 @@ class Registry < Dry::Struct
       end
 
       # Override or additional attributes
-      attribute :options,     ResourceRegistry::Entities::Option
-
+      attribute :options,     Types::Constructor(ResourceRegistry::Entities::Option)
+      end
     end
   end
 end
diff --git a/lib/resource_registry/entities/setting.rb b/lib/resource_registry/entities/setting.rb
index 2b3fdb73..1d14398f 100644
--- a/lib/resource_registry/entities/setting.rb
+++ b/lib/resource_registry/entities/setting.rb
@@ -1,16 +1,18 @@
+require 'resource_registry/entities/dry_struct_setters'
+
 module ResourceRegistry
   module Entities
-    class Setting < Dry::Struct
-      include DryStructSetters
-      transform_keys(&:to_sym)
+    class Setting
+      extend Dry::Initializer
 
-      attribute :key,            Types::Symbol
-      attribute :title?,         Types::String
-      attribute :description?,   Types::String
-      attribute :type?,          Types::Symbol
-      attribute :default?,       Types::Any
-      attribute :value?,         Types::Any
-    
+      option :key, type: Dry::Types["coercible.symbol"]
+      option :title, type: Types::String, optional: true
+      option :description, type: Types::String, optional: true
+      option :type, type: Dry::Types["coercible.symbol"], optional: true
+      option :default, type: Types::Any, optional: true
+      option :value, type: Types::Any, optional: true
     end
+
+    SettingConstructor = Types.Constructor(Setting) { |val| Setting.new(val) }
   end
 end
\ No newline at end of file
diff --git a/lib/resource_registry/options/validation/option_contract.rb b/lib/resource_registry/options/validation/option_contract.rb
index ff368610..d0ce4f72 100644
--- a/lib/resource_registry/options/validation/option_contract.rb
+++ b/lib/resource_registry/options/validation/option_contract.rb
@@ -1,15 +1,47 @@
 require 'dry/validation'
-require 'resource_registry/registries/validation/registry_contract'
+require File.expand_path(File.join(File.dirname(__FILE__), "setting_contract"))
 
 module ResourceRegistry
   module Options
     module Validation
-      class OptionContract < ResourceRegistry::Validation::ApplicationContract
+      unless defined?(MAX_OPTION_DEPTH)
+        MAX_OPTION_DEPTH = 15
+      end
+
+      class BottomNamespaceContract < ResourceRegistry::Validation::ApplicationContract
+        params do
+          required(:key).filled(Dry::Types["string"] | Dry::Types["symbol"])
+          optional(:settings).array(SettingContract.__schema__)
+        end
+      end
+
+      eval <<-RUBYCODE
+      class NamespaceLevel#{MAX_OPTION_DEPTH}Contract < ResourceRegistry::Validation::ApplicationContract
+        params do
+          required(:key).filled(Dry::Types["string"] | Dry::Types["symbol"])
+          optional(:settings).array(SettingContract.__schema__)
+          optional(:namespaces).array(BottomNamespaceContract.__schema__)
+        end
+      end
+      RUBYCODE
+
+      (1..(MAX_OPTION_DEPTH - 1)).to_a.reverse.each do |i|
+      eval(<<-RUBYCODE)
+      class NamespaceLevel#{i}Contract < ResourceRegistry::Validation::ApplicationContract
+        params do
+          required(:key).filled(Dry::Types["string"] | Dry::Types["symbol"])
+          optional(:settings).array(SettingContract.__schema__)
+          optional(:namespaces).array(NamespaceLevel#{i + 1}Contract.__schema__)
+        end
+      end
+      RUBYCODE
+      end
 
+      class OptionContract < ResourceRegistry::Validation::ApplicationContract
         params do
-          required(:key).filled(:string)
-          optional(:settings).array(type?: SettingContract)
-          optional(:namespaces).array(type?: OptionContract)
+          required(:key).filled(Dry::Types["string"] | Dry::Types["symbol"])
+          optional(:settings).array(SettingContract.__schema__)
+          optional(:namespaces).array(NamespaceLevel1Contract.__schema__)
         end
       end
     end
diff --git a/lib/resource_registry/options/validation/option_schema.rb b/lib/resource_registry/options/validation/option_schema.rb
deleted file mode 100644
index 3618d0c1..00000000
--- a/lib/resource_registry/options/validation/option_schema.rb
+++ /dev/null
@@ -1,14 +0,0 @@
-module ResourceRegistry
-  module Options
-    module Validation
-      class OptionSchema < ResourceRegistry::Validation::ApplicationSchema
-
-        define do
-          required(:key).filled(:symbol)
-          optional(:settings).array(type?: SettingSchema)
-          optional(:namespaces).array(type?: OptionSchema)
-        end
-      end
-    end
-  end
-end
\ No newline at end of file
diff --git a/lib/resource_registry/options/validation/setting_contract.rb b/lib/resource_registry/options/validation/setting_contract.rb
index c5149b74..9e34b199 100644
--- a/lib/resource_registry/options/validation/setting_contract.rb
+++ b/lib/resource_registry/options/validation/setting_contract.rb
@@ -7,12 +7,12 @@ module Validation
       class SettingContract < ResourceRegistry::Validation::ApplicationContract
 
         params do
-          required(:key).filled(:symbol)
-          required(:default).filled(:string)
+          required(:key).filled(Dry::Types["string"] | Dry::Types["symbol"])
+          required(:default).filled(:any)
           optional(:title).filled(:string)
           optional(:description).filled(:string)
-          optional(:type).filled(:string)
-          optional(:value).filled(:string)
+          optional(:type).filled(Dry::Types["string"] | Dry::Types["symbol"])
+          optional(:value).filled(:any)
         end
 
       end
diff --git a/lib/resource_registry/options/validation/setting_schema.rb b/lib/resource_registry/options/validation/setting_schema.rb
deleted file mode 100644
index 2922a87a..00000000
--- a/lib/resource_registry/options/validation/setting_schema.rb
+++ /dev/null
@@ -1,17 +0,0 @@
-module ResourceRegistry
-  module Options
-    module Validation
-      class SettingSchema < ResourceRegistry::Validation::ApplicationSchema
-
-        define do
-          required(:key).filled(:symbol)
-          required(:default).filled(:any)
-          optional(:title).filled(:string)
-          optional(:description).filled(:string)
-          optional(:type).filled(:string)
-          optional(:value).filled(:any)
-        end
-      end
-    end
-  end
-end
diff --git a/lib/resource_registry/serializers/operations/generate_option.rb b/lib/resource_registry/serializers/operations/generate_option.rb
index 7c58ba10..88e55604 100644
--- a/lib/resource_registry/serializers/operations/generate_option.rb
+++ b/lib/resource_registry/serializers/operations/generate_option.rb
@@ -1,42 +1,21 @@
+require File.expand_path(File.join(File.dirname(__FILE__), "../..", "options/validation/option_contract"))
+
 module ResourceRegistry
   module Serializers
     module Operations
       class GenerateOption
-        
         include Dry::Transaction::Operation
 
         def call(input)
-          option = convert(result: input)
-          return Success(option)
-        end
-
-        private
-
-        # def convert(input: nil)
-        #   input.symbolize_keys!
-
-        #   ResourceRegistry::Entities::Option.new(input)
-        # end
-
-        def convert(result: nil, parent_node: nil)
-          result.symbolize_keys!
-          if result.keys.include?(:namespaces) || result.keys.include?(:settings)
-            options = ResourceRegistry::Entities::Option.new(key: result[:key].to_sym)
-            root = options if parent_node.blank?
-            parent_node.namespaces = parent_node.namespaces.to_a + [options] if parent_node.present?
-            [:namespaces, :settings].each do |attrs|
-              result[attrs].each {|element| convert(result: element, parent_node: options) } if result[attrs].present?
-            end
+          schema = schema = ResourceRegistry::Options::Validation::OptionContract.new
+          result = schema.call(input)
+          
+          if result.success?
+            option = ResourceRegistry::Entities::Option.new(result.to_h)
+            Success(option)
           else
-            result.tap do |attrs|
-              attrs[:key] = attrs[:key].to_sym
-              attrs[:default] = attrs[:default]
-              attrs[:value] = attrs[:value] if attrs[:value].present?
-            end
-            setting  = ResourceRegistry::Entities::Setting.new(result)
-            parent_node.settings = parent_node.settings.to_a + [setting]
+            Failure(result.errors)
           end
-          root
         end
       end
     end
diff --git a/lib/resource_registry/serializers/operations/parse_yaml.rb b/lib/resource_registry/serializers/operations/parse_yaml.rb
index 3e1d3ee1..eb982e94 100644
--- a/lib/resource_registry/serializers/operations/parse_yaml.rb
+++ b/lib/resource_registry/serializers/operations/parse_yaml.rb
@@ -8,7 +8,7 @@ class ParseYaml
         include Dry::Transaction::Operation
 
         def call(input)
-          return Success(YAML.load(input))
+          Success(YAML.load(input))
         end
       end
     end
diff --git a/lib/resource_registry/serializers/option_generate.rb b/lib/resource_registry/serializers/option_generate.rb
index a04cfa75..48aa4e0b 100644
--- a/lib/resource_registry/serializers/option_generate.rb
+++ b/lib/resource_registry/serializers/option_generate.rb
@@ -4,93 +4,19 @@ class OptionGenerate
       include ResourceRegistry::Services::Service
       # include ResourceRegistry::PrivateInject["option_hash.validate"]
 
-      def call(**params)
+      def call(params)
         execute(params)
       end
 
       def execute(option_hash)
-
-        parse_hash(option_hash)
-        result = option_hash.validate
-
+        schema = ResourceRegistry::Options::Validation::OptionContract.new
+        result = schema.call(option_hash)
         if result.success?
-          parse_hash(option_hash)
+          ResourceRegistry::Entities::Option.new(result.to_h)
         else
-          # raise InvalidOptionHash if @content['namespace'].blank?
           raise InvalidOptionHash, "result.errors"
         end
       end
-
-
-      private
-
-      def convert(result: nil, parent_node: nil)
-        result.symbolize_keys!
-
-        if result.keys.include?(:namespaces) || result.keys.include?(:settings)
-          options = ResourceRegistry::Entities::Option.new(key: result[:key].to_sym)
-          root = options if parent_node.blank?
-          parent_node.namespaces = parent_node.namespaces.to_a + [options] if parent_node.present?
-          [:namespaces, :settings].each do |attrs|
-            result[attrs].each {|element| convert(result: element, parent_node: options) } if result[attrs].present?
-          end
-        else
-          result.tap do |attrs|
-            attrs[:key] = attrs[:key].to_sym
-            attrs[:default] = attrs[:default].to_s
-            attrs[:value] = attrs[:value].to_s if attrs[:value].present?
-          end
-          setting  = ResourceRegistry::Entities::Setting.new(result)
-          parent_node.settings = parent_node.settings.to_a + [setting]
-        end
-
-        root
-      end
-
-      def parse_hash(hash_tree, ns_stack = [], namespaces = [], settings = [])
-        option_list = []
-
-        hash_tree.each_pair do |key, nodes|
-          case key
-          when :namespace
-            ns_stack = []
-            ns_stack.push key.to_s
-            nodes.delete(:key)
-
-          when :namespaces
-            option_list << nodes.reduce([]) do |list, node|
-              ns_stack.push key.to_s
-              node.delete(:key)
-              node.reduce([]) do |list, child_node|
-                parse_hash(child_node, ns_stack, namespaces, settings)
-                hash_tree.delete(key)
-              end
-binding.pry
-              full_namespace = ns_stack.join('.')
-              list << ResourceRegistry::Entities::Option.new(key: full_namespace, namespaces: namespaces, settings: settings)
-binding.pry
-              nodes.delete(:key)
-              settings    = []
-              namespaces  = []
-            end
-
-binding.pry
-          when :settings
-            nodes.reduce([]) do | list, setting_hash | 
-              list << ResourceRegistry::Entities::Setting.new(setting_hash)
-            end
-
-            # hash_tree.delete(:settings)
-            # parse_hash(hash_tree, ns_stack, namespaces, settings)
-          end
-
-          option_list
-
-        end
-      end
-
-
-
     end
   end
 end
\ No newline at end of file
diff --git a/spec/resource_registry/serializers/operations/generate_container_spec.rb b/spec/resource_registry/serializers/operations/generate_container_spec.rb
index 41cfff41..07ae254a 100644
--- a/spec/resource_registry/serializers/operations/generate_container_spec.rb
+++ b/spec/resource_registry/serializers/operations/generate_container_spec.rb
@@ -8,7 +8,7 @@
   context 'When valid option passed' do  
 
     let(:input) {
-       ResourceRegistry::Entities::Option.new(options_hash)
+       ResourceRegistry::Serializers::OptionGenerate.new.execute(options_hash)
     }
 
     let(:expected_keys) {
diff --git a/spec/resource_registry_spec.rb b/spec/resource_registry_spec.rb
index 00e60be0..3a2560c8 100644
--- a/spec/resource_registry_spec.rb
+++ b/spec/resource_registry_spec.rb
@@ -71,19 +71,22 @@
   context ".load_options" do
 
     before(:all) do
-      ResourceRegistry.load_options!(option_files_dir)
+      @result = ResourceRegistry.load_options!(option_files_dir)
+    end
+
+    it "loads successfully" do
+      expect(@result.success?).to be_truthy
     end
 
     it 'should load site options' do
       expect(Registry.keys.include?("tenants.dchbx.applications.enroll.features")).to be_truthy
-      expect(Registry.keys.include?("tenants.dchbx.applications.edi.features")).to be_truthy
     end
 
-    it 'should load shop market options' do
+    it 'should load individual market options' do
       expect(Registry.keys.any?{|key| key.scan(/tenants.dchbx.applications.enroll.features.individual_market/).present?}).to be_truthy
     end
 
-    it 'should load individual market options' do
+    it 'should load shop market options' do
       expect(Registry.keys.any?{|key| key.scan("tenants.dchbx.applications.enroll.features.aca_shop_market").present?}).to be_truthy
     end
   end