diff --git a/web_src/js/index.js b/web_src/js/index.js
index 0d60c21ccacc1..d32397855fae4 100644
--- a/web_src/js/index.js
+++ b/web_src/js/index.js
@@ -15,6 +15,7 @@ import initHeatmap from './features/heatmap.js';
 import initProject from './features/projects.js';
 import initServiceWorker from './features/serviceworker.js';
 import initMarkdownAnchors from './markdown/anchors.js';
+import initMarkdownCheckboxes from './markdown/checkboxes.js';
 import renderMarkdownContent from './markdown/content.js';
 import attachTribute from './features/tribute.js';
 import createColorPicker from './features/colorpicker.js';
@@ -2644,6 +2645,8 @@ $(document).ready(async () => {
     renderMarkdownContent(),
     initGithook(),
   ]);
+
+  initMarkdownCheckboxes();
 });
 
 function changeHash(hash) {
diff --git a/web_src/js/markdown/checkboxes.js b/web_src/js/markdown/checkboxes.js
new file mode 100644
index 0000000000000..9c4d3f150c76a
--- /dev/null
+++ b/web_src/js/markdown/checkboxes.js
@@ -0,0 +1,70 @@
+const checkboxMarkdownPattern = /\[[ x]]/g;
+
+/**
+ * Attaches `change` handlers to markdown rendered checkboxes in comments.
+ * When a checkbox value changes, the corresponding [ ] or [x] in the markdown string is set accordingly and sent to the server.
+ * On success it updates the raw-content on error it resets the checkbox to its original value.
+ */
+export default function initMarkdownCheckboxes() {
+  $('.comment .segment').each((_, segment) => {
+    const $segment = $(segment);
+    const $checkboxes = $segment.find('.render-content.markdown input:checkbox');
+
+    const onChange = async (ev, checkboxIndex) => {
+      const $checkbox = $(ev.target);
+      const checkboxMarkdown = $checkbox.is(':checked') ? '[x]' : '[ ]';
+
+      const $rawContent = $segment.find('.raw-content');
+      const oldContent = $rawContent.text();
+      const newContent = oldContent.replace(checkboxMarkdownPattern, replaceNthMatchWith(checkboxIndex, checkboxMarkdown));
+
+      if (newContent !== oldContent) {
+        disableAll($checkboxes);
+
+        try {
+          const url = $segment.find('.edit-content-zone').data('update-url');
+          const context = $segment.find('.edit-content-zone').data('context');
+
+          await submit(newContent, url, context);
+          $rawContent.text(newContent);
+        } catch (e) {
+          $checkbox.prop('checked', !$checkbox.is(':checked'));
+
+          console.error(e);
+        } finally {
+          enableAll($checkboxes);
+        }
+      }
+    };
+
+    enableAll($checkboxes);
+    $checkboxes.each((checkboxIndex, checkboxElement) => {
+      $(checkboxElement).on('change', (ev) => onChange(ev, checkboxIndex));
+    });
+  });
+}
+
+function enableAll ($checkboxes) { $checkboxes.removeAttr('disabled') }
+function disableAll ($checkboxes) { $checkboxes.attr('disabled', 'disabled') }
+
+function submit (content, url, context) {
+  const csrf = window.config.csrf;
+
+  return $.post(url, {
+    _csrf: csrf,
+    context,
+    content,
+  });
+}
+
+function replaceNthMatchWith(n, replaceWith) {
+  let matchIndex = 0;
+
+  return (match) => {
+    if (n === matchIndex++) {
+      return replaceWith;
+    }
+
+    return match;
+  };
+}