diff --git a/Gemfile b/Gemfile
index 965df16..e66b026 100644
--- a/Gemfile
+++ b/Gemfile
@@ -5,10 +5,15 @@ source 'https://rubygems.org'
 # Specify your gem's dependencies in errgonomic.gemspec
 gemspec
 
-gem 'rake', '~> 13.0', group: :development
-gem 'rspec', '~> 3.0', group: :development
-gem 'rubocop', group: :development
-gem 'rubocop-yard', group: :development
-gem 'solargraph', group: :development
+group :development do
+  gem 'rake', '~> 13.0'
+  gem 'rspec', '~> 3.0'
+  gem 'rubocop'
+  gem 'rubocop-yard'
+  gem 'solargraph'
+  gem 'activerecord'
+  gem 'sqlite3'
+  gem 'minitest'
+end
 
-# gem "standard", "~> 1.3", group: :development
+# gem "standard", "~> 1.3"
diff --git a/Gemfile.lock b/Gemfile.lock
index ca280a2..2ce428d 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -7,11 +7,36 @@ PATH
 GEM
   remote: https://rubygems.org/
   specs:
+    activemodel (8.0.2)
+      activesupport (= 8.0.2)
+    activerecord (8.0.2)
+      activemodel (= 8.0.2)
+      activesupport (= 8.0.2)
+      timeout (>= 0.4.0)
+    activesupport (8.0.2)
+      base64
+      benchmark (>= 0.3)
+      bigdecimal
+      concurrent-ruby (~> 1.0, >= 1.3.1)
+      connection_pool (>= 2.2.5)
+      drb
+      i18n (>= 1.6, < 2)
+      logger (>= 1.4.2)
+      minitest (>= 5.1)
+      securerandom (>= 0.3)
+      tzinfo (~> 2.0, >= 2.0.5)
+      uri (>= 0.13.1)
     ast (2.4.2)
     backport (1.2.0)
+    base64 (0.2.0)
     benchmark (0.4.0)
+    bigdecimal (3.1.9)
     concurrent-ruby (1.3.5)
+    connection_pool (2.5.1)
     diff-lcs (1.6.0)
+    drb (2.2.1)
+    i18n (1.14.7)
+      concurrent-ruby (~> 1.0)
     jaro_winkler (1.6.0)
     json (2.10.1)
     kramdown (2.5.1)
@@ -69,6 +94,7 @@ GEM
       rubocop (~> 1.21)
       yard
     ruby-progressbar (1.13.0)
+    securerandom (0.4.1)
     solargraph (0.52.0)
       backport (~> 1.2)
       benchmark
@@ -88,11 +114,17 @@ GEM
       tilt (~> 2.0)
       yard (~> 0.9, >= 0.9.24)
       yard-solargraph (~> 0.1)
+    sqlite3 (2.6.0)
+      mini_portile2 (~> 2.8.0)
     thor (1.3.2)
     tilt (2.6.0)
+    timeout (0.4.3)
+    tzinfo (2.0.6)
+      concurrent-ruby (~> 1.0)
     unicode-display_width (3.1.4)
       unicode-emoji (~> 4.0, >= 4.0.4)
     unicode-emoji (4.0.4)
+    uri (1.0.3)
     yard (0.9.37)
     yard-doctest (0.1.17)
       minitest
@@ -104,12 +136,15 @@ PLATFORMS
   ruby
 
 DEPENDENCIES
+  activerecord
   errgonomic!
+  minitest
   rake (~> 13.0)
   rspec (~> 3.0)
   rubocop
   rubocop-yard
   solargraph
+  sqlite3
   yard (~> 0.9)
   yard-doctest (~> 0.1)
 
diff --git a/gemset.nix b/gemset.nix
index 22b520a..fdb1e5f 100644
--- a/gemset.nix
+++ b/gemset.nix
@@ -1,4 +1,37 @@
 {
+  activemodel = {
+    dependencies = ["activesupport"];
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0v35y2jzqlfy1wnrzlzj2cxylhnz09vykaa1l2dnkq7sl5zzpq8a";
+      type = "gem";
+    };
+    version = "8.0.2";
+  };
+  activerecord = {
+    dependencies = ["activemodel" "activesupport" "timeout"];
+    groups = ["development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "02nrya34qviawdkssyahb3mg08kqdc461b320a6ikr245jwp0d3r";
+      type = "gem";
+    };
+    version = "8.0.2";
+  };
+  activesupport = {
+    dependencies = ["base64" "benchmark" "bigdecimal" "concurrent-ruby" "connection_pool" "drb" "i18n" "logger" "minitest" "securerandom" "tzinfo" "uri"];
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0pm40y64wfc50a9sj87kxvil2102rmpdcbv82zf0r40vlgdwsrc5";
+      type = "gem";
+    };
+    version = "8.0.2";
+  };
   ast = {
     groups = ["default"];
     platforms = [];
@@ -19,6 +52,16 @@
     };
     version = "1.2.0";
   };
+  base64 = {
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "01qml0yilb9basf7is2614skjp8384h2pycfx86cr8023arfj98g";
+      type = "gem";
+    };
+    version = "0.2.0";
+  };
   benchmark = {
     groups = ["default"];
     platforms = [];
@@ -29,6 +72,16 @@
     };
     version = "0.4.0";
   };
+  bigdecimal = {
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1k6qzammv9r6b2cw3siasaik18i6wjc5m0gw5nfdc6jj64h79z1g";
+      type = "gem";
+    };
+    version = "3.1.9";
+  };
   concurrent-ruby = {
     groups = ["default"];
     platforms = [];
@@ -39,6 +92,16 @@
     };
     version = "1.3.5";
   };
+  connection_pool = {
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "171yzazg2wccbc545hwsx85sba91k7k1imir3c88385mlj82m05f";
+      type = "gem";
+    };
+    version = "2.5.1";
+  };
   diff-lcs = {
     groups = ["default"];
     platforms = [];
@@ -49,6 +112,16 @@
     };
     version = "1.6.0";
   };
+  drb = {
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0h5kbj9hvg5hb3c7l425zpds0vb42phvln2knab8nmazg2zp5m79";
+      type = "gem";
+    };
+    version = "2.2.1";
+  };
   errgonomic = {
     dependencies = ["concurrent-ruby"];
     groups = ["default"];
@@ -59,6 +132,17 @@
     };
     version = "0.2.0";
   };
+  i18n = {
+    dependencies = ["concurrent-ruby"];
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "03sx3ahz1v5kbqjwxj48msw3maplpp2iyzs22l4jrzrqh4zmgfnf";
+      type = "gem";
+    };
+    version = "1.14.7";
+  };
   jaro_winkler = {
     groups = ["default"];
     platforms = [];
@@ -362,6 +446,16 @@
     };
     version = "1.13.0";
   };
+  securerandom = {
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1cd0iriqfsf1z91qg271sm88xjnfd92b832z49p1nd542ka96lfc";
+      type = "gem";
+    };
+    version = "0.4.1";
+  };
   solargraph = {
     dependencies = ["backport" "benchmark" "diff-lcs" "jaro_winkler" "kramdown" "kramdown-parser-gfm" "logger" "observer" "ostruct" "parser" "rbs" "reverse_markdown" "rubocop" "thor" "tilt" "yard" "yard-solargraph"];
     groups = ["default"];
@@ -373,6 +467,17 @@
     };
     version = "0.52.0";
   };
+  sqlite3 = {
+    dependencies = ["mini_portile2"];
+    groups = ["development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0573vgz5ck0hqr8h132ln0hczx53m21h4w42n1p75rj837qjbim1";
+      type = "gem";
+    };
+    version = "2.6.0";
+  };
   thor = {
     groups = ["default"];
     platforms = [];
@@ -393,6 +498,27 @@
     };
     version = "2.6.0";
   };
+  timeout = {
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "03p31w5ghqfsbz5mcjzvwgkw3h9lbvbknqvrdliy8pxmn9wz02cm";
+      type = "gem";
+    };
+    version = "0.4.3";
+  };
+  tzinfo = {
+    dependencies = ["concurrent-ruby"];
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "16w2g84dzaf3z13gxyzlzbf748kylk5bdgg3n1ipvkvvqy685bwd";
+      type = "gem";
+    };
+    version = "2.0.6";
+  };
   unicode-display_width = {
     dependencies = ["unicode-emoji"];
     groups = ["default"];
@@ -414,6 +540,16 @@
     };
     version = "4.0.4";
   };
+  uri = {
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "04bhfvc25b07jaiaf62yrach7khhr5jlr5bx6nygg8pf11329wp9";
+      type = "gem";
+    };
+    version = "1.0.3";
+  };
   yard = {
     groups = ["development"];
     platforms = [];
diff --git a/lib/errgonomic.rb b/lib/errgonomic.rb
index 348e7df..f9de496 100644
--- a/lib/errgonomic.rb
+++ b/lib/errgonomic.rb
@@ -9,6 +9,9 @@
 require_relative 'errgonomic/option'
 require_relative 'errgonomic/result'
 
+# Rails fu
+require_relative 'errgonomic/rails' if defined?(Rails::Railtie)
+
 # Errgonomic adds opinionated abstractions to handle errors in a way that blends
 # Rust and Ruby ergonomics. This library leans on Rails conventions for some
 # presence-related methods; when in doubt, make those feel like Rails. It also
diff --git a/lib/errgonomic/rails.rb b/lib/errgonomic/rails.rb
new file mode 100644
index 0000000..494cf39
--- /dev/null
+++ b/lib/errgonomic/rails.rb
@@ -0,0 +1,40 @@
+require_relative 'option'
+require_relative 'rails/active_record_optional'
+require_relative 'rails/active_record_delegate_optional'
+
+module Errgonomic
+  # Rails specific functionality to integrate Errgonomic with minimum fuss.
+  module Rails
+    # We provide helper class methods, like `delegate_optional`,
+    # which need to be included into ActiveRecord::Base before any models are
+    # evaluated.
+    def self.setup_before
+      ActiveRecord::Base.include(Errgonomic::Rails::ActiveRecordDelegateOptional)
+    end
+
+    # Wrapping optional associations requires that we include the module after
+    # the class is first evaluated, so that it can define its associations for
+    # later reflection.
+    def self.setup_after
+      ActiveRecord::Base.descendants.each do |model|
+        model.include Errgonomic::Rails::ActiveRecordOptional if model.table_name
+      end
+    end
+  end
+end
+
+# TODO: Implement a Railtie to hook in the setup_before and setup_after at the
+# appropriate times for the Rails application lifecycle, in dev and prod.
+#
+# if defined?(Rails::Railtie)
+#   module Errgonomic::Rails
+#     class Railtie < Rails::Railtie
+#       initializer 'errgonomic.rails.setup_before' do
+#         Errgonomic::Rails.setup_before
+#       end
+#       initializer 'errgonomic.rails.setup_after' do
+#         Errgonomic::Rails.setup_after
+#       end
+#     end
+#   end
+# end
diff --git a/lib/errgonomic/rails/active_record_delegate_optional.rb b/lib/errgonomic/rails/active_record_delegate_optional.rb
new file mode 100644
index 0000000..5a384ac
--- /dev/null
+++ b/lib/errgonomic/rails/active_record_delegate_optional.rb
@@ -0,0 +1,22 @@
+module Errgonomic
+  module Rails
+    module ActiveRecordDelegateOptional
+      extend ActiveSupport::Concern
+
+      class_methods do
+        def delegate_optional(*methods, to: nil, prefix: nil, private: nil)
+          return if to.nil?
+
+          methods.each do |method_name|
+            prefixed_method_name = prefix == true ? "#{to}_#{method_name}" : method_name
+            class_eval <<-RUBY, __FILE__, __LINE__ + 1
+              def #{prefixed_method_name}
+                #{to}.map { |obj| obj.send(:#{method_name}) }
+              end
+            RUBY
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/lib/errgonomic/rails/active_record_optional.rb b/lib/errgonomic/rails/active_record_optional.rb
new file mode 100644
index 0000000..7bc2792
--- /dev/null
+++ b/lib/errgonomic/rails/active_record_optional.rb
@@ -0,0 +1,92 @@
+# frozen_string_literal: true
+
+module Errgonomic
+  module Rails
+    # Concern to make ActiveRecord optional attributes and associations return an Option.
+    #
+    module ActiveRecordOptional
+      extend ActiveSupport::Concern
+      included do
+        # ::Rails.logger.debug('ActiveRecordOptional')
+        optional_associations = reflect_on_all_associations(:belongs_to)
+                                .select { |r| r.options[:optional] }
+                                .map(&:name)
+        optional_attributes = column_names
+                              .select { |n| column_for_attribute(n).null }
+        (optional_attributes + optional_associations).each do |name|
+          # Rails.logger.debug("#{self.name}: #{name}: optional")
+          class_eval <<-RUBY, __FILE__, __LINE__ + 1
+        def #{name}
+          raise "stack too deep" if caller.length > 1024
+          val = super
+          val.nil? ? Errgonomic::Option::None.new : Errgonomic::Option::Some.new(val)
+        end
+          RUBY
+        end
+      end
+    end
+  end
+end
+
+# do we need this since we alias present below?
+class SomeValidator < ActiveModel::EachValidator
+  def validate_each(record, attribute, value)
+    record.errors.add(attribute, 'is invalid') unless value.some?
+  end
+end
+
+module Errgonomic
+  module Option
+    class Any
+      alias some? present?
+      alias none? blank?
+    end
+
+    class Some
+      delegate :marked_for_destruction?, to: :value
+      delegate :persisted?, to: :value
+      delegate :touch_later, to: :value
+
+      def to_s
+        raise "Attempted to convert Some to String, please use Option API to safely work with internal value -- #{value}"
+      end
+    end
+
+    class None
+      def nil?
+        true
+      end
+
+      def to_s
+        raise 'Cannot convert None to String - please use Option API to safely work with internal value'
+      end
+    end
+  end
+end
+
+module ActiveRecordOptionShim
+  def type_cast(value)
+    case value
+    when Errgonomic::Option::Some
+      super(value.unwrap!)
+    when Errgonomic::Option::None
+      super(nil)
+    else
+      super
+    end
+  end
+end
+
+ActiveRecord::ConnectionAdapters::Quoting.prepend(ActiveRecordOptionShim)
+
+class NilClass
+  def to_option
+    None()
+  end
+end
+
+class Object
+  def to_option
+    Some(self)
+  end
+end
diff --git a/test/rails_test.rb b/test/rails_test.rb
new file mode 100644
index 0000000..041c671
--- /dev/null
+++ b/test/rails_test.rb
@@ -0,0 +1,79 @@
+require 'active_record'
+require 'minitest/autorun'
+require 'logger'
+
+require_relative '../lib/errgonomic/rails'
+
+ActiveRecord::Base.establish_connection(adapter: 'sqlite3', database: ':memory:')
+ActiveRecord::Base.logger = Logger.new(File::NULL)
+
+# Book reviews with various optional attributes and associations
+ActiveRecord::Schema.define do
+  create_table 'authors', force: :cascade do |t|
+    t.string :name, null: false
+    t.text :bio
+    t.timestamps
+  end
+
+  create_table 'books', force: :cascade do |t|
+    t.string :title, null: false
+    t.string :isbn
+    t.date :published_at
+    t.references :author
+    t.references :genre
+    t.timestamps
+  end
+
+  create_table 'genres', force: :cascade do |t|
+    t.string :name, null: false
+    t.references :parent, foreign_key: { to_table: :genres }
+    t.timestamps
+  end
+end
+
+# Before classes are loaded we need to define helper methods like `delegate_optional`
+Errgonomic::Rails.setup_before
+
+class Author < ActiveRecord::Base
+  has_many :books
+end
+
+class Book < ActiveRecord::Base
+  has_many :reviews
+  has_many :reviewers, through: :reviews, source: :user
+  belongs_to :author, optional: true
+
+  delegate_optional :name, to: :author, prefix: true
+end
+
+class Genre < ActiveRecord::Base
+  has_many :books
+  belongs_to :parent, class_name: 'Genre', optional: true
+end
+
+# Optional associations have to be defined after the model is evaluated so we
+# can reflect on those associations.
+Errgonomic::Rails.setup_after
+
+class BugTest < Minitest::Test
+  def test_optional_attributes
+    author = Author.create!(name: 'Cixin Liu')
+    assert author.name.present?
+    assert author.bio.none?
+    book = author.books.create!(title: 'The Three-Body Problem')
+    assert book.isbn.none?
+  end
+
+  def test_optional_associations
+    author = Author.create!(name: 'Cixin Liu')
+    book = author.books.create!(title: 'The Dark Forest')
+    assert book.author.some?
+  end
+
+  def test_delegate_optional
+    author = Author.create!(name: 'Cixin Liu')
+    book = author.books.create!(title: 'Death\'s End')
+    assert book.author_name.some?
+    assert_equal author.name, book.author_name.unwrap!
+  end
+end