diff --git a/app/controllers/rules_controller.rb b/app/controllers/rules_controller.rb
index 24927b295..cd8a6eb6c 100644
--- a/app/controllers/rules_controller.rb
+++ b/app/controllers/rules_controller.rb
@@ -104,6 +104,30 @@ class RulesController < ApplicationController
     redirect_to rules_path, notice: "All rules deleted"
   end
 
+  def confirm_all
+    @rules = Current.family.rules
+    @total_affected_count = Rule.total_affected_resource_count(@rules)
+
+    # Compute AI cost estimation if any rule has auto_categorize action
+    if @rules.any? { |r| r.actions.any? { |a| a.action_type == "auto_categorize" } }
+      llm_provider = Provider::Registry.get_provider(:openai)
+
+      if llm_provider
+        @selected_model = Provider::Openai.effective_model
+        @estimated_cost = LlmUsage.estimate_auto_categorize_cost(
+          transaction_count: @total_affected_count,
+          category_count: Current.family.categories.count,
+          model: @selected_model
+        )
+      end
+    end
+  end
+
+  def apply_all
+    ApplyAllRulesJob.perform_later(Current.family)
+    redirect_back_or_to rules_path, notice: t("rules.apply_all.success")
+  end
+
   private
     def set_rule
       @rule = Current.family.rules.find(params[:id])
diff --git a/app/jobs/apply_all_rules_job.rb b/app/jobs/apply_all_rules_job.rb
new file mode 100644
index 000000000..f14da7091
--- /dev/null
+++ b/app/jobs/apply_all_rules_job.rb
@@ -0,0 +1,9 @@
+class ApplyAllRulesJob < ApplicationJob
+  queue_as :medium_priority
+
+  def perform(family, execution_type: "manual")
+    family.rules.find_each do |rule|
+      RuleJob.perform_now(rule, ignore_attribute_locks: true, execution_type: execution_type)
+    end
+  end
+end
diff --git a/app/models/rule.rb b/app/models/rule.rb
index 13087f93b..cd18deadc 100644
--- a/app/models/rule.rb
+++ b/app/models/rule.rb
@@ -40,6 +40,20 @@ class Rule < ApplicationRecord
     matching_resources_scope.count
   end
 
+  # Calculates total unique resources affected across multiple rules
+  # This handles overlapping rules by deduplicating transaction IDs
+  def self.total_affected_resource_count(rules)
+    return 0 if rules.empty?
+
+    # Collect all unique transaction IDs matched by any rule
+    transaction_ids = Set.new
+    rules.each do |rule|
+      transaction_ids.merge(rule.send(:matching_resources_scope).pluck(:id))
+    end
+
+    transaction_ids.size
+  end
+
   def apply(ignore_attribute_locks: false, rule_run: nil)
     total_modified = 0
     total_async_jobs = 0
diff --git a/app/views/rules/confirm_all.html.erb b/app/views/rules/confirm_all.html.erb
new file mode 100644
index 000000000..c88778767
--- /dev/null
+++ b/app/views/rules/confirm_all.html.erb
@@ -0,0 +1,48 @@
+<%= render DS::Dialog.new do |dialog| %>
+  <% dialog.with_header(title: t("rules.apply_all.confirm_title")) %>
+
+  <% dialog.with_body do %>
+    <p class="text-secondary text-sm mb-4">
+      <%= t("rules.apply_all.confirm_message",
+            count: @rules.count,
+            transactions: @total_affected_count) %>
+    </p>
+
+    <% if @rules.any? { |r| r.actions.any? { |a| a.action_type == "auto_categorize" } } %>
+      <div class="mb-4 p-3 bg-blue-50 border border-blue-200 rounded-lg">
+        <div class="flex items-start gap-2">
+          <%= icon "info", class: "w-4 h-4 text-blue-600 mt-0.5 flex-shrink-0" %>
+          <div class="text-xs">
+            <p class="font-medium text-blue-900 mb-1"><%= t("rules.apply_all.ai_cost_title") %></p>
+            <% if @estimated_cost.present? %>
+              <p class="text-blue-700">
+                <%= t("rules.apply_all.ai_cost_message", transactions: @total_affected_count) %>
+                <%= t("rules.apply_all.estimated_cost", cost: sprintf("%.4f", @estimated_cost)) %>
+              </p>
+            <% else %>
+              <p class="text-blue-700">
+                <%= t("rules.apply_all.ai_cost_message", transactions: @total_affected_count) %>
+                <% if @selected_model.present? %>
+                  <span class="font-semibold"><%= t("rules.apply_all.cost_unavailable_model", model: @selected_model) %></span>
+                <% else %>
+                  <span class="font-semibold"><%= t("rules.apply_all.cost_unavailable_no_provider") %></span>
+                <% end %>
+                <%= t("rules.apply_all.cost_warning") %>
+              </p>
+            <% end %>
+            <p class="text-blue-600 mt-1">
+              <%= link_to t("rules.apply_all.view_usage"), settings_llm_usage_path, class: "underline hover:text-blue-800" %>
+            </p>
+          </div>
+        </div>
+      </div>
+    <% end %>
+
+    <%= render DS::Button.new(
+      text: t("rules.apply_all.confirm_button"),
+      href: apply_all_rules_path,
+      method: :post,
+      full_width: true,
+      data: { turbo_frame: "_top" }) %>
+  <% end %>
+<% end %>
diff --git a/app/views/rules/index.html.erb b/app/views/rules/index.html.erb
index f40020abe..0acacb0fc 100644
--- a/app/views/rules/index.html.erb
+++ b/app/views/rules/index.html.erb
@@ -11,6 +11,13 @@
           method: :delete,
           confirm: CustomConfirm.for_resource_deletion("all rules", high_severity: true)) %>
       <% end %>
+      <%= render DS::Link.new(
+        text: t("rules.apply_all.button"),
+        variant: "secondary",
+        href: confirm_all_rules_path,
+        icon: "play",
+        frame: :modal
+      ) %>
     <% end %>
     <%= render DS::Link.new(
       text: "New rule",
diff --git a/config/locales/views/rules/en.yml b/config/locales/views/rules/en.yml
index 2d258c411..5cbd252d5 100644
--- a/config/locales/views/rules/en.yml
+++ b/config/locales/views/rules/en.yml
@@ -4,6 +4,19 @@ en:
     no_action: No Action
     actions:
       value_placeholder: Enter a value
+    apply_all:
+      button: Apply All
+      confirm_title: Apply All Rules
+      confirm_message: You are about to apply %{count} rules affecting %{transactions} unique transactions. Please confirm if you wish to proceed.
+      confirm_button: Confirm and Apply All
+      success: All rules have been queued for execution
+      ai_cost_title: AI Cost Estimation
+      ai_cost_message: This will use AI to categorize up to %{transactions} transactions.
+      estimated_cost: "Estimated cost: ~$%{cost}"
+      cost_unavailable_model: Cost estimation unavailable for model "%{model}".
+      cost_unavailable_no_provider: Cost estimation unavailable (no LLM provider configured).
+      cost_warning: You may incur costs, please check with the model provider for the most up-to-date prices.
+      view_usage: View usage history
     recent_runs:
       title: Recent Runs
       description: View the execution history of your rules including success/failure status and transaction counts.
diff --git a/config/routes.rb b/config/routes.rb
index b425b5824..4f4f45d6a 100644
--- a/config/routes.rb
+++ b/config/routes.rb
@@ -219,6 +219,8 @@ Rails.application.routes.draw do
 
     collection do
       delete :destroy_all
+      get :confirm_all
+      post :apply_all
     end
   end
 
diff --git a/lib/tasks/rules.rake b/lib/tasks/rules.rake
new file mode 100644
index 000000000..0a5a5c79a
--- /dev/null
+++ b/lib/tasks/rules.rake
@@ -0,0 +1,33 @@
+namespace :rules do
+  desc "Apply all rules for a family"
+  task :apply_all, [ :family_id ] => :environment do |_t, args|
+    family_id = args[:family_id]
+
+    if family_id.blank?
+      puts "Usage: bin/rails rules:apply_all[family_id]"
+      exit 1
+    end
+
+    family = Family.find(family_id)
+    rules = family.rules
+
+    if rules.empty?
+      puts "No rules found for family #{family_id}"
+      exit 0
+    end
+
+    puts "Applying #{rules.count} rules for family #{family_id}..."
+
+    rules.find_each do |rule|
+      print "  Applying rule '#{rule.name || rule.id}'... "
+      begin
+        RuleJob.perform_now(rule, ignore_attribute_locks: true, execution_type: "manual")
+        puts "done"
+      rescue => e
+        puts "failed: #{e.message}"
+      end
+    end
+
+    puts "Finished applying all rules"
+  end
+end
diff --git a/test/controllers/rules_controller_test.rb b/test/controllers/rules_controller_test.rb
index a948f399d..681bac37b 100644
--- a/test/controllers/rules_controller_test.rb
+++ b/test/controllers/rules_controller_test.rb
@@ -179,4 +179,17 @@ class RulesControllerTest < ActionDispatch::IntegrationTest
 
     assert_redirected_to rules_url
   end
+
+  test "should get confirm_all" do
+    get confirm_all_rules_url
+    assert_response :success
+  end
+
+  test "apply_all enqueues job and redirects" do
+    assert_enqueued_with(job: ApplyAllRulesJob) do
+      post apply_all_rules_url
+    end
+
+    assert_redirected_to rules_url
+  end
 end
diff --git a/test/jobs/apply_all_rules_job_test.rb b/test/jobs/apply_all_rules_job_test.rb
new file mode 100644
index 000000000..68591c29d
--- /dev/null
+++ b/test/jobs/apply_all_rules_job_test.rb
@@ -0,0 +1,41 @@
+require "test_helper"
+
+class ApplyAllRulesJobTest < ActiveJob::TestCase
+  include EntriesTestHelper
+
+  setup do
+    @family = families(:empty)
+    @account = @family.accounts.create!(name: "Test Account", balance: 1000, currency: "USD", accountable: Depository.new)
+    @groceries_category = @family.categories.create!(name: "Groceries")
+  end
+
+  test "applies all rules for a family" do
+    # Create a rule
+    rule = Rule.create!(
+      family: @family,
+      resource_type: "transaction",
+      effective_date: 1.day.ago.to_date,
+      conditions: [ Rule::Condition.new(condition_type: "transaction_name", operator: "like", value: "Whole Foods") ],
+      actions: [ Rule::Action.new(action_type: "set_transaction_category", value: @groceries_category.id) ]
+    )
+
+    # Mock RuleJob to verify it gets called for each rule
+    RuleJob.expects(:perform_now).with(rule, ignore_attribute_locks: true, execution_type: "manual").once
+
+    ApplyAllRulesJob.perform_now(@family)
+  end
+
+  test "applies all rules with custom execution type" do
+    rule = Rule.create!(
+      family: @family,
+      resource_type: "transaction",
+      effective_date: 1.day.ago.to_date,
+      conditions: [ Rule::Condition.new(condition_type: "transaction_name", operator: "like", value: "Test") ],
+      actions: [ Rule::Action.new(action_type: "set_transaction_category", value: @groceries_category.id) ]
+    )
+
+    RuleJob.expects(:perform_now).with(rule, ignore_attribute_locks: true, execution_type: "scheduled").once
+
+    ApplyAllRulesJob.perform_now(@family, execution_type: "scheduled")
+  end
+end
diff --git a/test/models/rule_test.rb b/test/models/rule_test.rb
index bf082ec73..731199fab 100644
--- a/test/models/rule_test.rb
+++ b/test/models/rule_test.rb
@@ -201,4 +201,39 @@ class RuleTest < ActiveSupport::TestCase
     assert_equal business_category, transaction_entry.transaction.category, "Transaction with 'business' in notes should be categorized"
     assert_nil transaction_entry2.transaction.category, "Transaction without 'business' in notes should not be categorized"
   end
+
+  test "total_affected_resource_count deduplicates overlapping rules" do
+    # Create transactions
+    transaction_entry1 = create_transaction(date: Date.current, account: @account, name: "Whole Foods", amount: 50)
+    transaction_entry2 = create_transaction(date: Date.current, account: @account, name: "Whole Foods", amount: 100)
+    transaction_entry3 = create_transaction(date: Date.current, account: @account, name: "Target", amount: 75)
+
+    # Rule 1: Match transactions with name "Whole Foods" (matches txn 1 and 2)
+    rule1 = Rule.create!(
+      family: @family,
+      resource_type: "transaction",
+      effective_date: 1.day.ago.to_date,
+      conditions: [ Rule::Condition.new(condition_type: "transaction_name", operator: "like", value: "Whole Foods") ],
+      actions: [ Rule::Action.new(action_type: "set_transaction_category", value: @groceries_category.id) ]
+    )
+
+    # Rule 2: Match transactions with amount > 60 (matches txn 2 and 3)
+    rule2 = Rule.create!(
+      family: @family,
+      resource_type: "transaction",
+      effective_date: 1.day.ago.to_date,
+      conditions: [ Rule::Condition.new(condition_type: "transaction_amount", operator: ">", value: 60) ],
+      actions: [ Rule::Action.new(action_type: "set_transaction_category", value: @groceries_category.id) ]
+    )
+
+    # Rule 1 affects 2 transactions, Rule 2 affects 2 transactions
+    # But transaction_entry2 is matched by both, so total unique should be 3
+    assert_equal 2, rule1.affected_resource_count
+    assert_equal 2, rule2.affected_resource_count
+    assert_equal 3, Rule.total_affected_resource_count([ rule1, rule2 ])
+  end
+
+  test "total_affected_resource_count returns zero for empty rules" do
+    assert_equal 0, Rule.total_affected_resource_count([])
+  end
 end