diff --git a/engine/app/assets/stylesheets/coplan/application.css b/engine/app/assets/stylesheets/coplan/application.css
index 103b67d..fd0bb4d 100644
--- a/engine/app/assets/stylesheets/coplan/application.css
+++ b/engine/app/assets/stylesheets/coplan/application.css
@@ -707,6 +707,26 @@ img.avatar {
   line-height: 1.9;
 }
 
+.markdown-rendered .task-list {
+  list-style: none;
+  padding-left: var(--space-md);
+}
+
+.markdown-rendered .task-list-item label {
+  display: flex;
+  align-items: baseline;
+  gap: var(--space-sm);
+  cursor: pointer;
+}
+
+.markdown-rendered .task-list-item input[type="checkbox"] {
+  cursor: pointer;
+  flex-shrink: 0;
+  margin: 0;
+  position: relative;
+  top: 1px;
+}
+
 .markdown-rendered pre {
   background: #f6f8fa;
   border: 1px solid var(--color-border);
diff --git a/engine/app/controllers/coplan/plans_controller.rb b/engine/app/controllers/coplan/plans_controller.rb
index d600399..1fb7b1d 100644
--- a/engine/app/controllers/coplan/plans_controller.rb
+++ b/engine/app/controllers/coplan/plans_controller.rb
@@ -1,6 +1,6 @@
 module CoPlan
   class PlansController < ApplicationController
-    before_action :set_plan, only: [:show, :edit, :update, :update_status]
+    before_action :set_plan, only: [:show, :edit, :update, :update_status, :toggle_checkbox]
 
     def index
       @plans = Plan.includes(:plan_type, :tags).order(updated_at: :desc)
@@ -51,6 +51,64 @@ def update_status
       end
     end
 
+    def toggle_checkbox
+      authorize!(@plan, :show?)
+
+      old_text = params[:old_text]
+      new_text = params[:new_text]
+      base_revision = params[:base_revision]&.to_i
+
+      unless old_text.present? && new_text.present? && base_revision.present?
+        render json: { error: "old_text, new_text, and base_revision are required" }, status: :unprocessable_content
+        return
+      end
+
+      checkbox_pattern = /\A\s*[*+-]\s+\[[ xX]\]\s/
+      unless old_text.match?(checkbox_pattern) && new_text.match?(checkbox_pattern)
+        render json: { error: "old_text and new_text must be task list items" }, status: :unprocessable_content
+        return
+      end
+
+      ActiveRecord::Base.transaction do
+        @plan.lock!
+        @plan.reload
+
+        if @plan.current_revision != base_revision
+          render json: { error: "Conflict", current_revision: @plan.current_revision }, status: :conflict
+          return
+        end
+
+        current_content = @plan.current_content || ""
+        result = Plans::ApplyOperations.call(
+          content: current_content,
+          operations: [{ "op" => "replace_exact", "old_text" => old_text, "new_text" => new_text }]
+        )
+
+        new_revision = @plan.current_revision + 1
+        diff = Diffy::Diff.new(current_content, result[:content]).to_s
+
+        version = PlanVersion.create!(
+          plan: @plan,
+          revision: new_revision,
+          content_markdown: result[:content],
+          actor_type: "human",
+          actor_id: current_user.id,
+          change_summary: "Toggle checkbox",
+          diff_unified: diff.presence,
+          operations_json: result[:applied],
+          base_revision: base_revision
+        )
+
+        @plan.update!(current_plan_version: version, current_revision: new_revision)
+        @plan.comment_threads.mark_out_of_date_for_new_version!(version)
+      end
+
+      broadcast_plan_update(@plan)
+      render json: { revision: @plan.current_revision }
+    rescue Plans::OperationError => e
+      render json: { error: e.message }, status: :unprocessable_content
+    end
+
     private
 
     def set_plan
diff --git a/engine/app/helpers/coplan/markdown_helper.rb b/engine/app/helpers/coplan/markdown_helper.rb
index 618556b..5b92cd1 100644
--- a/engine/app/helpers/coplan/markdown_helper.rb
+++ b/engine/app/helpers/coplan/markdown_helper.rb
@@ -6,7 +6,7 @@ module MarkdownHelper
       ul ol li
       table thead tbody tfoot tr th td
       pre code
-      a img
+      a img input label
       strong em b i u s del
       blockquote hr br
       dd dt dl
@@ -14,12 +14,13 @@ module MarkdownHelper
       details summary
     ].freeze
 
-    ALLOWED_ATTRIBUTES = %w[id class href src alt title].freeze
+    ALLOWED_ATTRIBUTES = %w[id class href src alt title type checked disabled data-line-text data-action data-coplan--checkbox-target].freeze
 
     def render_markdown(content)
       html = Commonmarker.to_html(content.to_s.encode("UTF-8"), options: { render: { unsafe: true } }, plugins: { syntax_highlighter: nil })
       sanitized = sanitize(html, tags: ALLOWED_TAGS, attributes: ALLOWED_ATTRIBUTES)
-      tag.div(sanitized, class: "markdown-rendered")
+      interactive = make_checkboxes_interactive(sanitized, content)
+      tag.div(interactive.html_safe, class: "markdown-rendered")
     end
 
     def markdown_to_plain_text(content)
@@ -38,5 +39,54 @@ def render_line_view(content)
 
       tag.div(safe_join(line_divs), class: "line-view", data: { controller: "line-selection" })
     end
+
+    private
+
+    def make_checkboxes_interactive(html, content)
+      doc = Nokogiri::HTML::DocumentFragment.parse(html)
+      checkboxes = doc.css('input[type="checkbox"]')
+      return html if checkboxes.empty?
+
+      task_lines = extract_task_lines(content)
+
+      checkboxes.each_with_index do |cb, i|
+        line_text = task_lines[i]
+        next unless line_text
+
+        cb.remove_attribute("disabled")
+        cb["data-action"] = "coplan--checkbox#toggle"
+        cb["data-coplan--checkbox-target"] = "checkbox"
+        cb["data-line-text"] = line_text
+
+        li = cb.parent
+        next unless li&.name == "li"
+        li.add_class("task-list-item")
+
+        # Wrap li contents in a <label> so the whole text is clickable
+        label = Nokogiri::XML::Node.new("label", doc)
+        li.children.each { |child| label.add_child(child) }
+        li.add_child(label)
+
+        ul = li.parent
+        ul.add_class("task-list") if ul&.name == "ul"
+      end
+
+      doc.to_html
+    end
+
+    def extract_task_lines(content)
+      lines = []
+      in_fence = false
+      content.to_s.each_line do |line|
+        stripped = line.rstrip
+        if stripped.match?(/\A(`{3,}|~{3,})/)
+          in_fence = !in_fence
+          next
+        end
+        next if in_fence
+        lines << stripped if stripped.match?(/^\s*[*+-]\s+\[[ xX]\]\s/)
+      end
+      lines
+    end
   end
 end
diff --git a/engine/app/javascript/controllers/coplan/checkbox_controller.js b/engine/app/javascript/controllers/coplan/checkbox_controller.js
new file mode 100644
index 0000000..dc3be38
--- /dev/null
+++ b/engine/app/javascript/controllers/coplan/checkbox_controller.js
@@ -0,0 +1,68 @@
+import { Controller } from "@hotwired/stimulus"
+
+export default class extends Controller {
+  static values = { planId: String, revision: Number, toggleUrl: String }
+  static targets = ["checkbox"]
+
+  toggle(event) {
+    const checkbox = event.target
+    const lineText = checkbox.dataset.lineText
+    if (!lineText) return
+    if (this.inflight) { checkbox.checked = !checkbox.checked; return }
+
+    const nowChecked = checkbox.checked
+    const oldText = lineText
+    const newText = nowChecked
+      ? lineText.replace(/([*+-]\s+)\[[ ]\]/, "$1[x]")
+      : lineText.replace(/([*+-]\s+)\[[xX]\]/, "$1[ ]")
+
+    // Optimistic UI: update immediately
+    checkbox.dataset.lineText = newText
+
+    this.inflight = true
+    this.#sendToggle({ checkbox, oldText, newText, nowChecked, retried: false })
+  }
+
+  #sendToggle({ checkbox, oldText, newText, nowChecked, retried }) {
+    const token = document.querySelector('meta[name="csrf-token"]')?.content
+
+    fetch(this.toggleUrlValue, {
+      method: "PATCH",
+      headers: {
+        "Content-Type": "application/json",
+        "X-CSRF-Token": token,
+        "Accept": "application/json"
+      },
+      body: JSON.stringify({
+        old_text: oldText,
+        new_text: newText,
+        base_revision: this.revisionValue
+      })
+    }).then(response => {
+      if (response.ok) {
+        return response.json().then(data => {
+          this.revisionValue = data.revision
+          this.inflight = false
+        })
+      } else if (response.status === 409 && !retried) {
+        // Conflict: someone else edited. Update revision and retry once.
+        return response.json().then(data => {
+          if (data.current_revision) {
+            this.revisionValue = data.current_revision
+          }
+          this.#sendToggle({ checkbox, oldText, newText, nowChecked, retried: true })
+        })
+      } else {
+        this.#revert(checkbox, oldText, nowChecked)
+      }
+    }).catch(() => {
+      this.#revert(checkbox, oldText, nowChecked)
+    })
+  }
+
+  #revert(checkbox, oldText, nowChecked) {
+    checkbox.checked = !nowChecked
+    checkbox.dataset.lineText = oldText
+    this.inflight = false
+  }
+}
diff --git a/engine/app/views/coplan/plans/show.html.erb b/engine/app/views/coplan/plans/show.html.erb
index 6f05d50..28ccdfe 100644
--- a/engine/app/views/coplan/plans/show.html.erb
+++ b/engine/app/views/coplan/plans/show.html.erb
@@ -17,7 +17,7 @@
 
 <div class="plan-content card">
   <% if @plan.current_content.present? %>
-    <div class="plan-layout" data-controller="coplan--text-selection coplan--content-nav" data-coplan--text-selection-plan-id-value="<%= @plan.id %>" data-coplan--text-selection-focus-thread-value="<%= params[:thread] %>" data-action="keydown.esc@document->coplan--text-selection#dismiss">
+    <div class="plan-layout" data-controller="coplan--text-selection coplan--content-nav coplan--checkbox" data-coplan--text-selection-plan-id-value="<%= @plan.id %>" data-coplan--text-selection-focus-thread-value="<%= params[:thread] %>" data-action="keydown.esc@document->coplan--text-selection#dismiss" data-coplan--checkbox-plan-id-value="<%= @plan.id %>" data-coplan--checkbox-revision-value="<%= @plan.current_revision %>" data-coplan--checkbox-toggle-url-value="<%= toggle_checkbox_plan_path(@plan) %>">
       <nav class="content-nav" data-coplan--content-nav-target="sidebar" aria-label="Document outline">
         <div class="content-nav__header">
           <span class="content-nav__title">Contents</span>
diff --git a/engine/config/routes.rb b/engine/config/routes.rb
index 7abfbe8..ae6fb3e 100644
--- a/engine/config/routes.rb
+++ b/engine/config/routes.rb
@@ -1,6 +1,7 @@
 CoPlan::Engine.routes.draw do
   resources :plans, only: [:index, :show, :edit, :update] do
     patch :update_status, on: :member
+    patch :toggle_checkbox, on: :member
     resources :versions, controller: "plan_versions", only: [:index, :show]
     resources :automated_reviews, only: [:create]
     resources :comment_threads, only: [:create] do
diff --git a/spec/helpers/coplan/markdown_helper_checkbox_spec.rb b/spec/helpers/coplan/markdown_helper_checkbox_spec.rb
new file mode 100644
index 0000000..f3dfd56
--- /dev/null
+++ b/spec/helpers/coplan/markdown_helper_checkbox_spec.rb
@@ -0,0 +1,99 @@
+require "rails_helper"
+
+RSpec.describe CoPlan::MarkdownHelper, type: :helper do
+  before do
+    helper.extend(CoPlan::MarkdownHelper)
+  end
+
+  describe "#render_markdown with task lists" do
+    it "renders unchecked task items as interactive checkboxes" do
+      html = helper.render_markdown("- [ ] Buy milk")
+      expect(html).to include('type="checkbox"')
+      expect(html).not_to include("disabled")
+      expect(html).to include('data-action="coplan--checkbox#toggle"')
+      expect(html).to include('data-coplan--checkbox-target="checkbox"')
+    end
+
+    it "renders checked task items as checked interactive checkboxes" do
+      html = helper.render_markdown("- [x] Buy milk")
+      expect(html).to include('type="checkbox"')
+      expect(html).to include("checked")
+      expect(html).not_to include("disabled")
+    end
+
+    it "sets data-line-text to the original markdown line" do
+      html = helper.render_markdown("- [ ] Buy milk")
+      expect(html).to include('data-line-text="- [ ] Buy milk"')
+    end
+
+    it "sets data-line-text for checked items" do
+      html = helper.render_markdown("- [x] Done task")
+      expect(html).to include('data-line-text="- [x] Done task"')
+    end
+
+    it "adds task-list class to parent ul" do
+      html = helper.render_markdown("- [ ] Item one\n- [x] Item two")
+      expect(html).to include('class="task-list"')
+    end
+
+    it "adds task-list-item class to li elements" do
+      html = helper.render_markdown("- [ ] Item")
+      expect(html).to include("task-list-item")
+    end
+
+    it "wraps checkbox li contents in a label for clickability" do
+      html = helper.render_markdown("- [ ] Click me")
+      doc = Nokogiri::HTML::DocumentFragment.parse(html)
+      label = doc.at_css("li.task-list-item label")
+      expect(label).to be_present
+      expect(label.at_css('input[type="checkbox"]')).to be_present
+    end
+
+    it "handles mixed task and non-task items" do
+      md = "- [ ] Task item\n- Regular item"
+      html = helper.render_markdown(md)
+      expect(html).to include('type="checkbox"')
+      expect(html).to include("Regular item")
+    end
+
+    it "handles multiple task lists" do
+      md = "- [ ] First\n- [x] Second\n\nSome text\n\n- [ ] Third"
+      html = helper.render_markdown(md)
+      doc = Nokogiri::HTML::DocumentFragment.parse(html)
+      checkboxes = doc.css('input[type="checkbox"]')
+      expect(checkboxes.length).to eq(3)
+      expect(checkboxes[0]["data-line-text"]).to eq("- [ ] First")
+      expect(checkboxes[1]["data-line-text"]).to eq("- [x] Second")
+      expect(checkboxes[2]["data-line-text"]).to eq("- [ ] Third")
+    end
+
+    it "does not affect regular lists" do
+      html = helper.render_markdown("- Item one\n- Item two")
+      expect(html).not_to include('type="checkbox"')
+      expect(html).not_to include("task-list")
+    end
+
+    it "preserves markdown-rendered wrapper class" do
+      html = helper.render_markdown("- [ ] Item")
+      expect(html).to include('class="markdown-rendered"')
+    end
+
+    it "ignores task lines inside fenced code blocks" do
+      md = "```\n- [ ] Fake checkbox\n```\n\n- [ ] Real checkbox"
+      html = helper.render_markdown(md)
+      doc = Nokogiri::HTML::DocumentFragment.parse(html)
+      checkboxes = doc.css('input[type="checkbox"]')
+      expect(checkboxes.length).to eq(1)
+      expect(checkboxes[0]["data-line-text"]).to eq("- [ ] Real checkbox")
+    end
+
+    it "preserves indentation in data-line-text for nested tasks" do
+      md = "- [ ] Parent\n  - [ ] Nested child"
+      html = helper.render_markdown(md)
+      doc = Nokogiri::HTML::DocumentFragment.parse(html)
+      checkboxes = doc.css('input[type="checkbox"]')
+      nested = checkboxes.find { |cb| cb["data-line-text"]&.include?("Nested") }
+      expect(nested["data-line-text"]).to eq("  - [ ] Nested child")
+    end
+  end
+end
diff --git a/spec/requests/plans_spec.rb b/spec/requests/plans_spec.rb
index 2e49308..32b2521 100644
--- a/spec/requests/plans_spec.rb
+++ b/spec/requests/plans_spec.rb
@@ -89,7 +89,7 @@
   it "show plan wires up both text-selection and content-nav controllers" do
     get plan_path(plan)
     expect(response).to have_http_status(:success)
-    expect(response.body).to include('data-controller="coplan--text-selection coplan--content-nav"')
+    expect(response.body).to include('data-controller="coplan--text-selection coplan--content-nav coplan--checkbox"')
   end
 
   it "show plan shares content target between controllers" do
diff --git a/spec/requests/toggle_checkbox_spec.rb b/spec/requests/toggle_checkbox_spec.rb
new file mode 100644
index 0000000..7ca59e3
--- /dev/null
+++ b/spec/requests/toggle_checkbox_spec.rb
@@ -0,0 +1,114 @@
+require "rails_helper"
+
+RSpec.describe "Toggle Checkbox", type: :request do
+  let(:user) { create(:coplan_user) }
+  let(:other_user) { create(:coplan_user) }
+  let(:plan) { create(:plan, :considering, created_by_user: user) }
+
+  before do
+    sign_in_as(user)
+    plan.current_plan_version.update!(content_markdown: "# Tasks\n\n- [ ] Buy milk\n- [x] Write tests\n- [ ] Deploy")
+  end
+
+  describe "PATCH toggle_checkbox" do
+    it "checks an unchecked checkbox and creates a new version" do
+      expect {
+        patch toggle_checkbox_plan_path(plan), params: {
+          old_text: "- [ ] Buy milk",
+          new_text: "- [x] Buy milk",
+          base_revision: plan.current_revision
+        }, as: :json
+      }.to change(CoPlan::PlanVersion, :count).by(1)
+
+      expect(response).to have_http_status(:ok)
+      data = response.parsed_body
+      expect(data["revision"]).to eq(plan.current_revision + 1)
+
+      plan.reload
+      expect(plan.current_content).to include("- [x] Buy milk")
+    end
+
+    it "unchecks a checked checkbox" do
+      patch toggle_checkbox_plan_path(plan), params: {
+        old_text: "- [x] Write tests",
+        new_text: "- [ ] Write tests",
+        base_revision: plan.current_revision
+      }, as: :json
+
+      expect(response).to have_http_status(:ok)
+      plan.reload
+      expect(plan.current_content).to include("- [ ] Write tests")
+    end
+
+    it "attributes the version to the current user" do
+      patch toggle_checkbox_plan_path(plan), params: {
+        old_text: "- [ ] Buy milk",
+        new_text: "- [x] Buy milk",
+        base_revision: plan.current_revision
+      }, as: :json
+
+      version = plan.reload.current_plan_version
+      expect(version.actor_type).to eq("human")
+      expect(version.actor_id).to eq(user.id)
+      expect(version.change_summary).to eq("Toggle checkbox")
+    end
+
+    it "returns 409 on stale base_revision" do
+      stale_revision = plan.current_revision
+      # Simulate a concurrent edit by bumping the revision
+      new_version = create(:plan_version, plan: plan, revision: plan.current_revision + 1,
+                           content_markdown: plan.current_content, actor_id: user.id)
+      plan.update!(current_plan_version: new_version, current_revision: new_version.revision)
+
+      patch toggle_checkbox_plan_path(plan), params: {
+        old_text: "- [ ] Buy milk",
+        new_text: "- [x] Buy milk",
+        base_revision: stale_revision
+      }, as: :json
+
+      expect(response).to have_http_status(:conflict)
+    end
+
+    it "returns 422 when old_text is missing" do
+      patch toggle_checkbox_plan_path(plan), params: {
+        new_text: "- [x] Buy milk",
+        base_revision: plan.current_revision
+      }, as: :json
+
+      expect(response).to have_http_status(:unprocessable_content)
+    end
+
+    it "returns 422 when payload is not a checkbox toggle" do
+      patch toggle_checkbox_plan_path(plan), params: {
+        old_text: "arbitrary text to replace",
+        new_text: "sneaky replacement",
+        base_revision: plan.current_revision
+      }, as: :json
+
+      expect(response).to have_http_status(:unprocessable_content)
+      expect(response.parsed_body["error"]).to include("task list")
+    end
+
+    it "returns 422 when old_text is not found in content" do
+      patch toggle_checkbox_plan_path(plan), params: {
+        old_text: "- [ ] Nonexistent task",
+        new_text: "- [x] Nonexistent task",
+        base_revision: plan.current_revision
+      }, as: :json
+
+      expect(response).to have_http_status(:unprocessable_content)
+    end
+
+    it "allows toggle from non-author user" do
+      sign_in_as(other_user)
+
+      patch toggle_checkbox_plan_path(plan), params: {
+        old_text: "- [ ] Buy milk",
+        new_text: "- [x] Buy milk",
+        base_revision: plan.current_revision
+      }, as: :json
+
+      expect(response).to have_http_status(:ok)
+    end
+  end
+end
diff --git a/spec/system/checkbox_spec.rb b/spec/system/checkbox_spec.rb
new file mode 100644
index 0000000..3f9ebe7
--- /dev/null
+++ b/spec/system/checkbox_spec.rb
@@ -0,0 +1,166 @@
+require "rails_helper"
+
+RSpec.describe "Interactive checkboxes", type: :system do
+  let(:author) { create(:coplan_user, email: "author@example.com") }
+
+  let(:plan_content) do
+    <<~MARKDOWN
+      # Launch Checklist
+
+      - [ ] Write documentation
+      - [ ] Run load tests
+      - [x] Set up monitoring
+      - [ ] Get security review
+    MARKDOWN
+  end
+
+  let(:plan) do
+    p = CoPlan::Plan.create!(title: "Checklist Plan", created_by_user: author)
+    version = CoPlan::PlanVersion.create!(
+      plan: p, revision: 1,
+      content_markdown: plan_content, actor_type: "human", actor_id: author.id
+    )
+    p.update!(current_plan_version: version, current_revision: 1)
+    p
+  end
+
+  def sign_in(user)
+    visit sign_in_path
+    fill_in "Email address", with: user.email
+    click_button "Sign In"
+    expect(page).to have_current_path(root_path)
+    expect(page).to have_content("Sign out")
+  end
+
+  before { sign_in(author) }
+
+  it "renders task list items as interactive checkboxes" do
+    visit plan_path(plan)
+
+    checkboxes = all('input[type="checkbox"]')
+    expect(checkboxes.length).to eq(4)
+
+    expect(checkboxes[0]).not_to be_checked
+    expect(checkboxes[1]).not_to be_checked
+    expect(checkboxes[2]).to be_checked
+    expect(checkboxes[3]).not_to be_checked
+  end
+
+  it "renders checkboxes without the disabled attribute" do
+    visit plan_path(plan)
+
+    disabled_values = page.evaluate_script(
+      'Array.from(document.querySelectorAll(\'input[type="checkbox"]\')).map(cb => cb.disabled)'
+    )
+    disabled_values.each do |val|
+      expect(val).to be false
+    end
+  end
+
+  it "adds task-list-item class to checkbox list items" do
+    visit plan_path(plan)
+
+    expect(page).to have_css("li.task-list-item", minimum: 4)
+  end
+
+  it "wraps checkbox items in labels for full-text clickability" do
+    visit plan_path(plan)
+
+    expect(page).to have_css("li.task-list-item label input[type='checkbox']", minimum: 4)
+  end
+
+  it "checks an unchecked checkbox and creates a new version" do
+    visit plan_path(plan)
+
+    initial_version_count = CoPlan::PlanVersion.count
+
+    # Find the first unchecked checkbox ("Write documentation")
+    checkbox = all('input[type="checkbox"]').first
+    expect(checkbox).not_to be_checked
+
+    checkbox.click
+    expect(checkbox).to be_checked
+
+    # Wait for the server response by checking the version was created
+    wait_for_version(plan, 2)
+
+    plan.reload
+    expect(plan.current_content).to include("- [x] Write documentation")
+    expect(CoPlan::PlanVersion.count).to eq(initial_version_count + 1)
+
+    version = plan.current_plan_version
+    expect(version.actor_id).to eq(author.id)
+    expect(version.change_summary).to eq("Toggle checkbox")
+  end
+
+  it "unchecks a checked checkbox" do
+    visit plan_path(plan)
+
+    checkbox = find('input[type="checkbox"][checked]')
+    expect(checkbox).to be_checked
+
+    checkbox.click
+    expect(checkbox).not_to be_checked
+
+    wait_for_version(plan, 2)
+
+    plan.reload
+    expect(plan.current_content).to include("- [ ] Set up monitoring")
+  end
+
+  it "updates data-line-text after toggling" do
+    visit plan_path(plan)
+
+    checkbox = all('input[type="checkbox"]').first
+    expect(checkbox["data-line-text"]).to eq("- [ ] Write documentation")
+
+    checkbox.click
+
+    wait_for_version(plan, 2)
+
+    updated_line_text = page.evaluate_script(
+      'document.querySelector(\'input[type="checkbox"]\').dataset.lineText'
+    )
+    expect(updated_line_text).to eq("- [x] Write documentation")
+  end
+
+  it "supports toggling multiple checkboxes in sequence" do
+    visit plan_path(plan)
+
+    first_cb = all('input[type="checkbox"]')[0]
+    first_cb.click
+    wait_for_version(plan, 2)
+
+    second_cb = all('input[type="checkbox"]')[1]
+    second_cb.click
+    wait_for_version(plan, 3)
+
+    plan.reload
+    expect(plan.current_revision).to eq(3)
+    expect(plan.current_content).to include("- [x] Write documentation")
+    expect(plan.current_content).to include("- [x] Run load tests")
+  end
+
+  it "toggles checkbox by clicking the label text" do
+    visit plan_path(plan)
+
+    label = find("li.task-list-item label", text: "Write documentation")
+    label.click
+
+    wait_for_version(plan, 2)
+
+    plan.reload
+    expect(plan.current_content).to include("- [x] Write documentation")
+  end
+
+  private
+
+  def wait_for_version(plan, expected_revision, timeout: 5)
+    Timeout.timeout(timeout) do
+      loop do
+        break if plan.class.find(plan.id).current_revision >= expected_revision
+        sleep 0.1
+      end
+    end
+  end
+end