diff --git a/app/models/concerns/taskable.rb b/app/models/concerns/taskable.rb
index 410e8dc820b..bbb3b301a9f 100644
--- a/app/models/concerns/taskable.rb
+++ b/app/models/concerns/taskable.rb
@@ -5,7 +5,7 @@
 # Used by MergeRequest and Issue
 module Taskable
   TASK_PATTERN_MD = /^(?<bullet> *[*-] *)\[(?<checked>[ xX])\]/.freeze
-  TASK_PATTERN_HTML = /^<li>\[(?<checked>[ xX])\]/.freeze
+  TASK_PATTERN_HTML = /^<li>(?<p_tag>\s*<p>)?\[(?<checked>[ xX])\]/.freeze
 
   # Change the state of a task list item for this Taskable.  Edit the object's
   # description by finding the nth task item and changing its checkbox
diff --git a/lib/gitlab/markdown.rb b/lib/gitlab/markdown.rb
index e02e5b9fc3d..f5e8267031c 100644
--- a/lib/gitlab/markdown.rb
+++ b/lib/gitlab/markdown.rb
@@ -352,11 +352,12 @@ module Gitlab
       # ActiveSupport::SafeBuffer, hence the `String.new`
       String.new(text).gsub(Taskable::TASK_PATTERN_HTML) do
         checked = $LAST_MATCH_INFO[:checked].downcase == 'x'
+        p_tag = $LAST_MATCH_INFO[:p_tag]
 
         if checked
-          "#{li_tag}#{checked_box}"
+          "#{li_tag}#{p_tag}#{checked_box}"
         else
-          "#{li_tag}#{unchecked_box}"
+          "#{li_tag}#{p_tag}#{unchecked_box}"
         end
       end
     end
diff --git a/spec/helpers/gitlab_markdown_helper_spec.rb b/spec/helpers/gitlab_markdown_helper_spec.rb
index 6ba27b536e4..ddbb4467f10 100644
--- a/spec/helpers/gitlab_markdown_helper_spec.rb
+++ b/spec/helpers/gitlab_markdown_helper_spec.rb
@@ -817,6 +817,17 @@ EOT
       )
     end
 
+    it 'should render checkboxes for nested tasks' do
+      rendered_text = markdown(@source_text_asterisk, parse_tasks: true)
+
+      expect(rendered_text).to match(
+        /<input.*checkbox.*valid unchecked nested task/
+      )
+      expect(rendered_text).to match(
+        /<input.*checkbox.*valid checked nested task/
+      )
+    end
+
     it 'should not be confused by whitespace before bullets' do
       rendered_text_asterisk = markdown(@source_text_asterisk,
                                         parse_tasks: true)