diff --git a/.annotaterb.yml b/.annotaterb.yml
new file mode 100644
index 00000000..89f547ae
--- /dev/null
+++ b/.annotaterb.yml
@@ -0,0 +1,64 @@
+---
+:position: before
+:position_in_additional_file_patterns: before
+:position_in_class: before
+:position_in_factory: before
+:position_in_fixture: before
+:position_in_routes: before
+:position_in_serializer: before
+:position_in_test: before
+:classified_sort: true
+:exclude_controllers: true
+:exclude_factories: false
+:exclude_fixtures: false
+:exclude_helpers: true
+:exclude_scaffolds: true
+:exclude_serializers: false
+:exclude_sti_subclasses: false
+:exclude_tests: false
+:force: false
+:format_markdown: false
+:format_rdoc: false
+:format_yard: false
+:frozen: false
+:grouped_polymorphic: false
+:ignore_model_sub_dir: false
+:ignore_unknown_models: false
+:include_version: false
+:show_check_constraints: false
+:show_complete_foreign_keys: false
+:show_foreign_keys: true
+:show_indexes: true
+:show_indexes_include: false
+:simple_indexes: false
+:sort: false
+:timestamp: false
+:trace: false
+:with_comment: true
+:with_column_comments: true
+:with_table_comments: true
+:position_of_column_comment: :with_name
+:active_admin: false
+:command:
+:debug: false
+:hide_default_column_types: ''
+:hide_limit_column_types: ''
+:timestamp_columns:
+- created_at
+- updated_at
+:ignore_columns:
+:ignore_routes:
+:models: true
+:routes: false
+:skip_on_db_migrate: false
+:target_action: :do_annotations
+:wrapper:
+:wrapper_close:
+:wrapper_open:
+:classes_default_to_s: []
+:additional_file_patterns: []
+:model_dir:
+- app/models
+:require: []
+:root_dir:
+- ''
diff --git a/Gemfile b/Gemfile
index 7711a8a2..89c8566b 100644
--- a/Gemfile
+++ b/Gemfile
@@ -81,6 +81,9 @@ group :development do
 
   # Use letter_opener to preview emails in the browser in development [https://github.com/ryanb/letter_opener]
   gem "letter_opener"
+
+  # Automatically annotate models with schema information
+  gem "annotaterb"
 end
 
 group :test do
diff --git a/Gemfile.lock b/Gemfile.lock
index 4072344d..5b88416f 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -74,6 +74,9 @@ GEM
       uri (>= 0.13.1)
     addressable (2.8.7)
       public_suffix (>= 2.0.2, < 7.0)
+    annotaterb (4.18.0)
+      activerecord (>= 6.0.0)
+      activesupport (>= 6.0.0)
     ast (2.4.3)
     base64 (0.3.0)
     bcrypt (3.1.20)
@@ -441,6 +444,7 @@ PLATFORMS
   x86_64-linux-musl
 
 DEPENDENCIES
+  annotaterb
   bcrypt (~> 3.1.7)
   bootsnap
   brakeman
diff --git a/app/models/org.rb b/app/models/org.rb
index ac624d1a..347a3b36 100644
--- a/app/models/org.rb
+++ b/app/models/org.rb
@@ -1,5 +1,18 @@
 # frozen_string_literal: true
 
+# == Schema Information
+#
+# Table name: orgs
+#
+#  id           :bigint           not null, primary key
+#  created_at   :datetime         not null
+#  updated_at   :datetime         not null
+#  clerk_org_id :string           not null
+#
+# Indexes
+#
+#  index_orgs_on_clerk_org_id  (clerk_org_id) UNIQUE
+#
 class Org < ApplicationRecord
   validates :clerk_org_id, presence: true, uniqueness: true
 end
diff --git a/app/models/user.rb b/app/models/user.rb
index 0f9262ee..fd1b1aa2 100644
--- a/app/models/user.rb
+++ b/app/models/user.rb
@@ -5,9 +5,9 @@
 # Table name: users
 #
 #  id         :bigint           not null, primary key
-#  clerk_id   :string           not null
 #  created_at :datetime         not null
 #  updated_at :datetime         not null
+#  clerk_id   :string           not null
 #
 # Indexes
 #
diff --git a/db/cable_schema.rb b/db/cable_schema.rb
index 7d9c3a0b..23e6a368 100644
--- a/db/cable_schema.rb
+++ b/db/cable_schema.rb
@@ -10,7 +10,7 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema[8.0].define(version: 2025_08_03_194905) do
+ActiveRecord::Schema[8.0].define(version: 2025_08_19_145110) do
   # These are extensions that must be enabled in order to support this database
   enable_extension "pg_catalog.plpgsql"
 
@@ -25,6 +25,7 @@
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
     t.string "clerk_id", null: false
+    t.string "test_field"
     t.index ["clerk_id"], name: "index_users_on_clerk_id", unique: true
   end
 end
diff --git a/db/cache_schema.rb b/db/cache_schema.rb
index 7d9c3a0b..23e6a368 100644
--- a/db/cache_schema.rb
+++ b/db/cache_schema.rb
@@ -10,7 +10,7 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema[8.0].define(version: 2025_08_03_194905) do
+ActiveRecord::Schema[8.0].define(version: 2025_08_19_145110) do
   # These are extensions that must be enabled in order to support this database
   enable_extension "pg_catalog.plpgsql"
 
@@ -25,6 +25,7 @@
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
     t.string "clerk_id", null: false
+    t.string "test_field"
     t.index ["clerk_id"], name: "index_users_on_clerk_id", unique: true
   end
 end
diff --git a/db/queue_schema.rb b/db/queue_schema.rb
index 7d9c3a0b..23e6a368 100644
--- a/db/queue_schema.rb
+++ b/db/queue_schema.rb
@@ -10,7 +10,7 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema[8.0].define(version: 2025_08_03_194905) do
+ActiveRecord::Schema[8.0].define(version: 2025_08_19_145110) do
   # These are extensions that must be enabled in order to support this database
   enable_extension "pg_catalog.plpgsql"
 
@@ -25,6 +25,7 @@
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
     t.string "clerk_id", null: false
+    t.string "test_field"
     t.index ["clerk_id"], name: "index_users_on_clerk_id", unique: true
   end
 end
diff --git a/lib/tasks/annotate_rb.rake b/lib/tasks/annotate_rb.rake
new file mode 100644
index 00000000..611cfe9e
--- /dev/null
+++ b/lib/tasks/annotate_rb.rake
@@ -0,0 +1,10 @@
+# frozen_string_literal: true
+
+# This rake task was added by annotate_rb gem.
+
+# Can set `ANNOTATERB_SKIP_ON_DB_TASKS` to be anything to skip this
+if Rails.env.development? && ENV["ANNOTATERB_SKIP_ON_DB_TASKS"].nil?
+  require "annotate_rb"
+
+  AnnotateRb::Core.load_rake_tasks
+end
diff --git a/spec/factories/users.rb b/spec/factories/users.rb
index 44cab328..01e49dd9 100644
--- a/spec/factories/users.rb
+++ b/spec/factories/users.rb
@@ -1,5 +1,18 @@
 # frozen_string_literal: true
 
+# == Schema Information
+#
+# Table name: users
+#
+#  id         :bigint           not null, primary key
+#  created_at :datetime         not null
+#  updated_at :datetime         not null
+#  clerk_id   :string           not null
+#
+# Indexes
+#
+#  index_users_on_clerk_id  (clerk_id) UNIQUE
+#
 FactoryBot.define do
   factory :user do
     sequence(:clerk_id) { |n| "user_#{n}_clerk_id" }