diff --git a/app/services/task_list_toggle_service.rb b/app/services/task_list_toggle_service.rb
index af24bc0524cb8a0a0635ee54b6543f36c73ade4b..f6602a3503352b5af670c005f169d6201c552e06 100644
--- a/app/services/task_list_toggle_service.rb
+++ b/app/services/task_list_toggle_service.rb
@@ -67,6 +67,6 @@ def toggle_markdown_html
   # When using CommonMark, we should be able to use the embedded `sourcepos` attribute to
   # target the exact line in the DOM.
   def get_html_checkbox(html)
-    html.css(".task-list-item[data-sourcepos^='#{line_number}:'] > input.task-list-item-checkbox").first
+    html.css(".task-list-item[data-sourcepos^='#{line_number}:'] input.task-list-item-checkbox").first
   end
 end
diff --git a/spec/services/task_list_toggle_service_spec.rb b/spec/services/task_list_toggle_service_spec.rb
index 7c5480d382f848ca2b9be9d94e38a4b8f772360c..b1260cf740af0689c740e614dea9eafdc9b2919c 100644
--- a/spec/services/task_list_toggle_service_spec.rb
+++ b/spec/services/task_list_toggle_service_spec.rb
@@ -12,6 +12,10 @@
 
       1. [X] Item 1
          - [ ] Sub-item 1
+
+      - [ ] loose list
+
+        with an embedded paragraph
     EOT
   end
 
@@ -26,16 +30,22 @@
         </li>
       </ul>
       <p data-sourcepos="4:1-4:11" dir="auto">A paragraph</p>
-      <ol data-sourcepos="6:1-7:19" class="task-list" dir="auto">
-        <li data-sourcepos="6:1-7:19" class="task-list-item">
-          <input type="checkbox" class="task-list-item-checkbox" disabled checked> Item 1
-          <ul data-sourcepos="7:4-7:19" class="task-list">
-            <li data-sourcepos="7:4-7:19" class="task-list-item">
-              <input type="checkbox" class="task-list-item-checkbox" disabled> Sub-item 1
+      <ol data-sourcepos="6:1-8:0" class="task-list" dir="auto">
+        <li data-sourcepos="6:1-8:0" class="task-list-item">
+          <input type="checkbox" class="task-list-item-checkbox" checked="" disabled=""> Item 1
+          <ul data-sourcepos="7:4-8:0" class="task-list">
+            <li data-sourcepos="7:4-8:0" class="task-list-item">
+              <input type="checkbox" class="task-list-item-checkbox" disabled=""> Sub-item 1
             </li>
           </ul>
         </li>
       </ol>
+      <ul data-sourcepos="9:1-11:28" class="task-list" dir="auto">
+        <li data-sourcepos="9:1-11:28" class="task-list-item">
+          <p data-sourcepos="9:3-9:16"><input type="checkbox" class="task-list-item-checkbox" disabled=""> loose list</p>
+          <p data-sourcepos="11:3-11:28">with an embedded paragraph</p>
+        </li>
+      </ul>
     EOT
   end
 
@@ -59,6 +69,16 @@
     expect(toggler.updated_markdown_html).to include('disabled> Item 1')
   end
 
+  it 'checks task in loose list' do
+    toggler = described_class.new(markdown, markdown_html,
+                                  toggle_as_checked: true,
+                                  line_source: '- [ ] loose list', line_number: 9)
+
+    expect(toggler.execute).to be_truthy
+    expect(toggler.updated_markdown.lines[8]).to eq "- [x] loose list\n"
+    expect(toggler.updated_markdown_html).to include('disabled checked> loose list')
+  end
+
   it 'returns false if line_source does not match the text' do
     toggler = described_class.new(markdown, markdown_html,
                                   toggle_as_checked: false,