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..9ce71e9 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -7,92 +7,130 @@ PATH
 GEM
   remote: https://rubygems.org/
   specs:
-    ast (2.4.2)
+    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 (2.4.3)
     backport (1.2.0)
-    benchmark (0.4.0)
+    base64 (0.3.0)
+    benchmark (0.4.1)
+    bigdecimal (3.2.2)
     concurrent-ruby (1.3.5)
-    diff-lcs (1.6.0)
-    jaro_winkler (1.6.0)
-    json (2.10.1)
+    connection_pool (2.5.3)
+    diff-lcs (1.6.2)
+    drb (2.2.3)
+    i18n (1.14.7)
+      concurrent-ruby (~> 1.0)
+    jaro_winkler (1.6.1)
+    json (2.12.2)
     kramdown (2.5.1)
       rexml (>= 3.3.9)
     kramdown-parser-gfm (1.1.0)
       kramdown (~> 2.0)
-    language_server-protocol (3.17.0.4)
-    logger (1.6.6)
-    mini_portile2 (2.8.8)
-    minitest (5.25.4)
-    nokogiri (1.18.3)
+    language_server-protocol (3.17.0.5)
+    lint_roller (1.1.0)
+    logger (1.7.0)
+    mini_portile2 (2.8.9)
+    minitest (5.25.5)
+    nokogiri (1.18.8)
       mini_portile2 (~> 2.8.2)
       racc (~> 1.4)
     observer (0.1.2)
-    ostruct (0.6.1)
-    parallel (1.26.3)
-    parser (3.3.7.1)
+    ostruct (0.6.2)
+    parallel (1.27.0)
+    parser (3.3.8.0)
       ast (~> 2.4.1)
       racc
+    prism (1.4.0)
     racc (1.8.1)
     rainbow (3.1.1)
-    rake (13.2.1)
-    rbs (3.8.1)
+    rake (13.3.0)
+    rbs (3.9.4)
       logger
     regexp_parser (2.10.0)
     reverse_markdown (3.0.0)
       nokogiri
     rexml (3.4.1)
-    rspec (3.13.0)
+    rspec (3.13.1)
       rspec-core (~> 3.13.0)
       rspec-expectations (~> 3.13.0)
       rspec-mocks (~> 3.13.0)
-    rspec-core (3.13.3)
+    rspec-core (3.13.5)
       rspec-support (~> 3.13.0)
-    rspec-expectations (3.13.3)
+    rspec-expectations (3.13.5)
       diff-lcs (>= 1.2.0, < 2.0)
       rspec-support (~> 3.13.0)
-    rspec-mocks (3.13.2)
+    rspec-mocks (3.13.5)
       diff-lcs (>= 1.2.0, < 2.0)
       rspec-support (~> 3.13.0)
-    rspec-support (3.13.2)
-    rubocop (1.71.2)
+    rspec-support (3.13.4)
+    rubocop (1.78.0)
       json (~> 2.3)
-      language_server-protocol (>= 3.17.0)
+      language_server-protocol (~> 3.17.0.2)
+      lint_roller (~> 1.1.0)
       parallel (~> 1.10)
       parser (>= 3.3.0.2)
       rainbow (>= 2.2.2, < 4.0)
       regexp_parser (>= 2.9.3, < 3.0)
-      rubocop-ast (>= 1.38.0, < 2.0)
+      rubocop-ast (>= 1.45.1, < 2.0)
       ruby-progressbar (~> 1.7)
       unicode-display_width (>= 2.4.0, < 4.0)
-    rubocop-ast (1.38.1)
-      parser (>= 3.3.1.0)
-    rubocop-yard (0.10.0)
-      rubocop (~> 1.21)
+    rubocop-ast (1.45.1)
+      parser (>= 3.3.7.2)
+      prism (~> 1.4)
+    rubocop-yard (1.0.0)
+      lint_roller
+      rubocop (~> 1.72)
       yard
     ruby-progressbar (1.13.0)
-    solargraph (0.52.0)
+    securerandom (0.4.1)
+    solargraph (0.56.0)
       backport (~> 1.2)
-      benchmark
+      benchmark (~> 0.4)
       bundler (~> 2.0)
       diff-lcs (~> 1.4)
-      jaro_winkler (~> 1.6)
+      jaro_winkler (~> 1.6, >= 1.6.1)
       kramdown (~> 2.3)
       kramdown-parser-gfm (~> 1.1)
       logger (~> 1.6)
       observer (~> 0.1)
       ostruct (~> 0.6)
       parser (~> 3.0)
-      rbs (~> 3.0)
-      reverse_markdown (>= 2.0, < 4)
+      prism (~> 1.4)
+      rbs (~> 3.3)
+      reverse_markdown (~> 3.0)
       rubocop (~> 1.38)
       thor (~> 1.0)
       tilt (~> 2.0)
       yard (~> 0.9, >= 0.9.24)
       yard-solargraph (~> 0.1)
+    sqlite3 (2.7.2)
+      mini_portile2 (~> 2.8.0)
     thor (1.3.2)
-    tilt (2.6.0)
+    tilt (2.6.1)
+    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
@@ -104,14 +142,17 @@ PLATFORMS
   ruby
 
 DEPENDENCIES
+  activerecord
   errgonomic!
+  minitest
   rake (~> 13.0)
   rspec (~> 3.0)
   rubocop
   rubocop-yard
   solargraph
+  sqlite3
   yard (~> 0.9)
   yard-doctest (~> 0.1)
 
 BUNDLED WITH
-   2.5.22
+   2.6.7
diff --git a/flake.lock b/flake.lock
index 9108411..6eabc6c 100644
--- a/flake.lock
+++ b/flake.lock
@@ -2,16 +2,16 @@
   "nodes": {
     "nixpkgs": {
       "locked": {
-        "lastModified": 1740463929,
-        "narHash": "sha256-4Xhu/3aUdCKeLfdteEHMegx5ooKQvwPHNkOgNCXQrvc=",
+        "lastModified": 1751741127,
+        "narHash": "sha256-t75Shs76NgxjZSgvvZZ9qOmz5zuBE8buUaYD28BMTxg=",
         "owner": "nixos",
         "repo": "nixpkgs",
-        "rev": "5d7db4668d7a0c6cc5fc8cf6ef33b008b2b1ed8b",
+        "rev": "29e290002bfff26af1db6f64d070698019460302",
         "type": "github"
       },
       "original": {
         "owner": "nixos",
-        "ref": "nixos-24.11",
+        "ref": "nixos-25.05",
         "repo": "nixpkgs",
         "type": "github"
       }
diff --git a/flake.nix b/flake.nix
index 7b270fa..5e52811 100644
--- a/flake.nix
+++ b/flake.nix
@@ -2,7 +2,7 @@
   description = "Errgonomic";
 
   inputs = {
-    nixpkgs.url = "github:nixos/nixpkgs?ref=nixos-24.11";
+    nixpkgs.url = "github:nixos/nixpkgs?ref=nixos-25.05";
   };
 
   outputs =
diff --git a/gemset.nix b/gemset.nix
index 22b520a..c168b26 100644
--- a/gemset.nix
+++ b/gemset.nix
@@ -1,16 +1,49 @@
 {
+  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"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "04nc8x27hlzlrr5c2gn7mar4vdr0apw5xg22wp6m8dx3wqr04a0y";
+      sha256 = "10yknjyn0728gjn6b5syynvrvrwm66bhssbxq8mkhshxghaiailm";
       type = "gem";
     };
-    version = "2.4.2";
+    version = "2.4.3";
   };
   backport = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
@@ -19,18 +52,38 @@
     };
     version = "1.2.0";
   };
+  base64 = {
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0yx9yn47a8lkfcjmigk79fykxvr80r4m1i35q82sxzynpbm7lcr7";
+      type = "gem";
+    };
+    version = "0.3.0";
+  };
   benchmark = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0jl71qcgamm96dzyqk695j24qszhcc7liw74qc83fpjljp2gh4hg";
+      sha256 = "1kicilpma5l0lwayqjb5577bm0hbjndj2gh150xz09xsgc1l1vyl";
       type = "gem";
     };
-    version = "0.4.0";
+    version = "0.4.1";
+  };
+  bigdecimal = {
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1p2szbr4jdvmwaaj2kxlbv1rp0m6ycbgfyp0kjkkkswmniv5y21r";
+      type = "gem";
+    };
+    version = "3.2.2";
   };
   concurrent-ruby = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
@@ -39,15 +92,35 @@
     };
     version = "1.3.5";
   };
+  connection_pool = {
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0nrhsk7b3sjqbyl1cah6ibf1kvi3v93a7wf4637d355hp614mmyg";
+      type = "gem";
+    };
+    version = "2.5.3";
+  };
   diff-lcs = {
-    groups = ["default"];
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0qlrj2qyysc9avzlr4zs1py3x684hqm61n4czrsk1pyllz5x5q4s";
+      type = "gem";
+    };
+    version = "1.6.2";
+  };
+  drb = {
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0bnss89lcm3b1k3xcjd35grxqz5q040d12imd73qybwnfarggrx1";
+      sha256 = "0wrkl7yiix268s2md1h6wh91311w95ikd8fy8m5gx589npyxc00b";
       type = "gem";
     };
-    version = "1.6.0";
+    version = "2.2.3";
   };
   errgonomic = {
     dependencies = ["concurrent-ruby"];
@@ -59,29 +132,40 @@
     };
     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"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "09645h5an19zc1i7wlmixszj8xxqb2zc8qlf8dmx39bxpas1l24b";
+      sha256 = "14xkw4lb6wwvbcwqkf6ds116sridk9c8yz6y3caw07vzpwdvcmn0";
       type = "gem";
     };
-    version = "1.6.0";
+    version = "1.6.1";
   };
   json = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1p4l5ycdxfsr8b51gnvlvhq6s21vmx9z4x617003zbqv3bcqmj6x";
+      sha256 = "1x5b8ipv6g0z44wgc45039k04smsyf95h2m5m67mqq35sa5a955s";
       type = "gem";
     };
-    version = "2.10.1";
+    version = "2.12.2";
   };
   kramdown = {
     dependencies = ["rexml"];
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
@@ -92,7 +176,7 @@
   };
   kramdown-parser-gfm = {
     dependencies = ["kramdown"];
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
@@ -102,58 +186,68 @@
     version = "1.1.0";
   };
   language_server-protocol = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0scnz2fvdczdgadvjn0j9d49118aqm3hj66qh8sd2kv6g1j65164";
+      sha256 = "1k0311vah76kg5m6zr7wmkwyk5p2f9d9hyckjpn3xgr83ajkj7px";
       type = "gem";
     };
-    version = "3.17.0.4";
+    version = "3.17.0.5";
+  };
+  lint_roller = {
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "11yc0d84hsnlvx8cpk4cbj6a4dz9pk0r1k29p0n1fz9acddq831c";
+      type = "gem";
+    };
+    version = "1.1.0";
   };
   logger = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "05s008w9vy7is3njblmavrbdzyrwwc1fsziffdr58w9pwqj8sqfx";
+      sha256 = "00q2zznygpbls8asz5knjvvj2brr3ghmqxgr83xnrdj4rk3xwvhr";
       type = "gem";
     };
-    version = "1.6.6";
+    version = "1.7.0";
   };
   mini_portile2 = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0x8asxl83msn815lwmb2d7q5p29p7drhjv5va0byhk60v9n16iwf";
+      sha256 = "12f2830x7pq3kj0v8nz0zjvaw02sv01bqs1zwdrc04704kwcgmqc";
       type = "gem";
     };
-    version = "2.8.8";
+    version = "2.8.9";
   };
   minitest = {
-    groups = ["default" "development"];
+    groups = ["development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0izrg03wn2yj3gd76ck7ifbm9h2kgy8kpg4fk06ckpy4bbicmwlw";
+      sha256 = "0mn7q9yzrwinvfvkyjiz548a4rmcwbmz2fn9nyzh4j1snin6q6rr";
       type = "gem";
     };
-    version = "5.25.4";
+    version = "5.25.5";
   };
   nokogiri = {
     dependencies = ["mini_portile2" "racc"];
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0npx535cs8qc33n0lpbbwl0p9fi3a5bczn6ayqhxvknh9yqw77vb";
+      sha256 = "0rb306hbky6cxfyc8vrwpvl40fdapjvhsk62h08gg9wwbn3n8x4c";
       type = "gem";
     };
-    version = "1.18.3";
+    version = "1.18.8";
   };
   observer = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
@@ -163,38 +257,48 @@
     version = "0.1.2";
   };
   ostruct = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "05xqijcf80sza5pnlp1c8whdaay8x5dc13214ngh790zrizgp8q9";
+      sha256 = "1h6gazp5837xbz1aqvq9x0a5ffpw32nhvknn931a4074k6i04wvd";
       type = "gem";
     };
-    version = "0.6.1";
+    version = "0.6.2";
   };
   parallel = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1vy7sjs2pgz4i96v5yk9b7aafbffnvq7nn419fgvw55qlavsnsyq";
+      sha256 = "0c719bfgcszqvk9z47w2p8j2wkz5y35k48ywwas5yxbbh3hm3haa";
       type = "gem";
     };
-    version = "1.26.3";
+    version = "1.27.0";
   };
   parser = {
     dependencies = ["ast" "racc"];
-    groups = ["default"];
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0i9w8msil4snx5w11ix9b0wf52vjc3r49khy3ddgl1xk890kcxi4";
+      type = "gem";
+    };
+    version = "3.3.8.0";
+  };
+  prism = {
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "18dcwrcnddvi8gl3hmbsb2cj1l7afxk2lh3jmhj90l95h1hn3gkx";
+      sha256 = "0gkhpdjib9zi9i27vd9djrxiwjia03cijmd6q8yj2q1ix403w3nw";
       type = "gem";
     };
-    version = "3.3.7.1";
+    version = "1.4.0";
   };
   racc = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
@@ -204,7 +308,7 @@
     version = "1.8.1";
   };
   rainbow = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
@@ -214,28 +318,28 @@
     version = "3.1.1";
   };
   rake = {
-    groups = ["default"];
+    groups = ["development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "17850wcwkgi30p7yqh60960ypn7yibacjjha0av78zaxwvd3ijs6";
+      sha256 = "14s4jdcs1a4saam9qmzbsa2bsh85rj9zfxny5z315x3gg0nhkxcn";
       type = "gem";
     };
-    version = "13.2.1";
+    version = "13.3.0";
   };
   rbs = {
     dependencies = ["logger"];
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "07cwjkx7b3ssy8ccqq1s34sc5snwvgxan2ikmp9y2rz2a9wy6v1b";
+      sha256 = "1mx533jn2nv29xc5faw9g5xj9qbdaiwl9wv2byv98bgw6gqwhhlf";
       type = "gem";
     };
-    version = "3.8.1";
+    version = "3.9.4";
   };
   regexp_parser = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
@@ -246,7 +350,7 @@
   };
   reverse_markdown = {
     dependencies = ["nokogiri"];
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
@@ -256,7 +360,7 @@
     version = "3.0.0";
   };
   rexml = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
@@ -267,93 +371,93 @@
   };
   rspec = {
     dependencies = ["rspec-core" "rspec-expectations" "rspec-mocks"];
-    groups = ["default"];
+    groups = ["development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "14xrp8vq6i9zx37vh0yp4h9m0anx9paw200l1r5ad9fmq559346l";
+      sha256 = "0h11wynaki22a40rfq3ahcs4r36jdpz9acbb3m5dkf0mm67sbydr";
       type = "gem";
     };
-    version = "3.13.0";
+    version = "3.13.1";
   };
   rspec-core = {
     dependencies = ["rspec-support"];
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1r6zbis0hhbik1ck8kh58qb37d1qwij1x1d2fy4jxkzryh3na4r5";
+      sha256 = "18sgga9zjrd5579m9rpb78l7yn9a0bjzwz51z5kiq4y6jwl6hgxb";
       type = "gem";
     };
-    version = "3.13.3";
+    version = "3.13.5";
   };
   rspec-expectations = {
     dependencies = ["diff-lcs" "rspec-support"];
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0n3cyrhsa75x5wwvskrrqk56jbjgdi2q1zx0irllf0chkgsmlsqf";
+      sha256 = "0dl8npj0jfpy31bxi6syc7jymyd861q277sfr6jawq2hv6hx791k";
       type = "gem";
     };
-    version = "3.13.3";
+    version = "3.13.5";
   };
   rspec-mocks = {
     dependencies = ["diff-lcs" "rspec-support"];
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1vxxkb2sf2b36d8ca2nq84kjf85fz4x7wqcvb8r6a5hfxxfk69r3";
+      sha256 = "10gajm8iscl7gb8q926hyna83bw3fx2zb4sqdzjrznjs51pqlcz4";
       type = "gem";
     };
-    version = "3.13.2";
+    version = "3.13.5";
   };
   rspec-support = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1v6v6xvxcpkrrsrv7v1xgf7sl0d71vcfz1cnrjflpf6r7x3a58yf";
+      sha256 = "1xx3f4mgr84jz07fifd3r68hm6giqy91hqyzawmi0s59yqa1hjqq";
       type = "gem";
     };
-    version = "3.13.2";
+    version = "3.13.4";
   };
   rubocop = {
-    dependencies = ["json" "language_server-protocol" "parallel" "parser" "rainbow" "regexp_parser" "rubocop-ast" "ruby-progressbar" "unicode-display_width"];
-    groups = ["default"];
+    dependencies = ["json" "language_server-protocol" "lint_roller" "parallel" "parser" "rainbow" "regexp_parser" "rubocop-ast" "ruby-progressbar" "unicode-display_width"];
+    groups = ["development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0zzrsdz23jmjc8iwilzhw5cifn4flzmsbwkzxlwa6qf6m80payws";
+      sha256 = "1h3b1pl0wawm9w6jad2w333xijjxykvzflc8hzkd6kzb2bwscx4b";
       type = "gem";
     };
-    version = "1.71.2";
+    version = "1.78.0";
   };
   rubocop-ast = {
-    dependencies = ["parser"];
-    groups = ["default"];
+    dependencies = ["parser" "prism"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1zjpv3kw4ciwk0dh43zj17ws318vnirby1clmcy6j9mvr4mbxv40";
+      sha256 = "0gis8w51k5dsmzzlppvwwznqyfd73fa3zcrpl1xihzy1mm4jw14l";
       type = "gem";
     };
-    version = "1.38.1";
+    version = "1.45.1";
   };
   rubocop-yard = {
-    dependencies = ["rubocop" "yard"];
+    dependencies = ["lint_roller" "rubocop" "yard"];
     groups = ["development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "03s8lwah6apkr1g25whhd9y2zrqq9dy56g5kwn0bxp0slakrpisz";
+      sha256 = "0k1pcbc7hahfchbivf8gn38rxxxv8p30vvnzihlr0sf3rdrzz4ai";
       type = "gem";
     };
-    version = "0.10.0";
+    version = "1.0.0";
   };
   ruby-progressbar = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
@@ -362,19 +466,40 @@
     };
     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"];
+    dependencies = ["backport" "benchmark" "diff-lcs" "jaro_winkler" "kramdown" "kramdown-parser-gfm" "logger" "observer" "ostruct" "parser" "prism" "rbs" "reverse_markdown" "rubocop" "thor" "tilt" "yard" "yard-solargraph"];
+    groups = ["development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0fqa486hfn6kdbqp3ppy3jvl9xyj8jz41a2dzgkhc6ny2pj31w92";
+      sha256 = "1jf8d19j32f3h99acmx9h4g5qaykxzb25fqp028g2bvqvl8k7r2r";
       type = "gem";
     };
-    version = "0.52.0";
+    version = "0.56.0";
+  };
+  sqlite3 = {
+    dependencies = ["mini_portile2"];
+    groups = ["development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1xf9pm1pvrny4by0sy7s9hlpz2kwij5p9gys77fwd87zqpgpcqs4";
+      type = "gem";
+    };
+    version = "2.7.2";
   };
   thor = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
@@ -384,18 +509,39 @@
     version = "1.3.2";
   };
   tilt = {
-    groups = ["default"];
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0w27v04d7rnxjr3f65w1m7xyvr6ch6szjj2v5wv1wz6z5ax9pa9m";
+      type = "gem";
+    };
+    version = "2.6.1";
+  };
+  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 = "0szpapi229v3scrvw1pgy0vpjm7z3qlf58m1198kxn70cs278g96";
+      sha256 = "16w2g84dzaf3z13gxyzlzbf748kylk5bdgg3n1ipvkvvqy685bwd";
       type = "gem";
     };
-    version = "2.6.0";
+    version = "2.0.6";
   };
   unicode-display_width = {
     dependencies = ["unicode-emoji"];
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
@@ -405,7 +551,7 @@
     version = "3.1.4";
   };
   unicode-emoji = {
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
@@ -414,6 +560,16 @@
     };
     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 = [];
@@ -437,7 +593,7 @@
   };
   yard-solargraph = {
     dependencies = ["yard"];
-    groups = ["default"];
+    groups = ["default" "development"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
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/option.rb b/lib/errgonomic/option.rb
index 15f0d7f..0dbff41 100644
--- a/lib/errgonomic/option.rb
+++ b/lib/errgonomic/option.rb
@@ -5,6 +5,10 @@ module Option
     # The base class for all options. Some and None are subclasses.
     #
     class Any
+      # def method_missing(_name, *_args)
+      #   raise 'do it right noob'
+      # end
+
       # An option of the same type with an equal inner value is equal.
       #
       # Because we're going to monkey patch this into other libraries Rails, we
@@ -98,7 +102,7 @@ def unwrap!
       # message
       # @example
       #   Some(1).expect!("msg") # => 1
-      #   None().expect!("msg") # => raise Errgonomic::ExpectError, "msg"
+      #   None().expect!("here's why this failed") # => raise Errgonomic::ExpectError, "here's why this failed"
       def expect!(msg)
         raise Errgonomic::ExpectError, msg if none?
 
@@ -115,6 +119,16 @@ def unwrap_or(default)
         value
       end
 
+      # # returns the inner value if present, else returns the default value
+      # # @example
+      # #   Some(1).unwrap_or(2) # => 1
+      # #   None().unwrap_or(2) # => 2
+      # def unwrap_or_default
+      #   self.class.respond_to?(:default) or raise
+      #   return self.class.default if none?
+      #   value
+      # end
+
       # returns the inner value if present, else returns the result of the
       # provided block
       # @example
@@ -302,6 +316,7 @@ def zip(other)
       #   Some(2).zip_with(Some(3)) { |a, b| a + b } # => Some(5)
       def zip_with(other, &block)
         return None() unless some? && other.some?
+
         other = block.call(value, other.value)
         Some(other)
       end
@@ -314,8 +329,6 @@ def zip_with(other, &block)
       # take
       # take_if
       # replace
-      # zip
-      # zip_with
     end
 
     # Represent a value
diff --git a/lib/errgonomic/rails.rb b/lib/errgonomic/rails.rb
new file mode 100644
index 0000000..26594de
--- /dev/null
+++ b/lib/errgonomic/rails.rb
@@ -0,0 +1,48 @@
+require_relative 'option'
+require_relative 'rails/active_record_optional'
+require_relative 'rails/active_record_delegate_optional'
+
+module Errgonomic
+  # Slightly more convenient access to the setup functions:
+  # Errgonomic::Rails.setup_before and Errgonomic::Rails.setup_after
+  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
+      Zeitwerk::Loader.eager_load_all
+      setupable = defined?(ApplicationRecord) ? ApplicationRecord : ActiveRecord::Base
+      setupable.descendants.each do |model|
+        next unless begin
+          model.table_exists?
+        rescue StandardError
+          false
+        end
+
+        model.include Errgonomic::Rails::ActiveRecordOptional
+      end
+    end
+  end
+
+  # Hook into Rails with a Railtie
+  class Railtie < ::Rails::Railtie
+    initializer 'errgonomic.setup_before' do
+      Errgonomic::Rails.setup_before
+    end
+    config.after_initialize do
+      ActiveSupport.on_load(:after_initialize) do
+        Errgonomic::Rails.setup_after
+      end
+    end
+    config.to_prepare do
+      Errgonomic::Rails.setup_after
+    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..75db1e7
--- /dev/null
+++ b/lib/errgonomic/rails/active_record_optional.rb
@@ -0,0 +1,99 @@
+# 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 }
+        @errgonomic_optionals = (optional_attributes + optional_associations)
+        @errgonomic_optionals.each do |name|
+          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
+
+      class_methods do
+        def errgonomic_optionals
+          @errgonomic_optionals
+        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