diff --git a/src/code-components/Combobox/Combobox.module.css b/src/code-components/Combobox/Combobox.module.css
index 151456ab..ff72ce50 100644
--- a/src/code-components/Combobox/Combobox.module.css
+++ b/src/code-components/Combobox/Combobox.module.css
@@ -36,6 +36,14 @@
 .positioner {
   transition: opacity 0.1s ease-in;
   overflow: visible !important;
+  /*
+   * The menu is portalled to `document.body`. A Radix modal dialog sets
+   * `pointer-events: none` on `body` while open and restores `auto` only on its
+   * own content element, so a menu opened from inside a dialog would render but
+   * ignore every click. `pointer-events` inherits, so re-enabling it here covers
+   * the whole menu subtree. Harmless outside a dialog.
+   */
+  pointer-events: auto;
 }
 
 .positioner[data-closed] {
diff --git a/src/code-components/DialogV2/DialogV2.tsx b/src/code-components/DialogV2/DialogV2.tsx
index c1aa3ba2..555ad598 100644
--- a/src/code-components/DialogV2/DialogV2.tsx
+++ b/src/code-components/DialogV2/DialogV2.tsx
@@ -62,6 +62,10 @@ export function DialogV2({
               event.preventDefault();
             }}
             onPointerDownOutside={(event) => {
+              if (isHeadlessUiPortalClick(event)) {
+                event.preventDefault();
+                return;
+              }
               preventEventIfScrollbarClick(event);
               onPointerDownOutside?.(event);
             }}
@@ -74,6 +78,19 @@ export function DialogV2({
   );
 }
 
+/**
+ * A Headless UI menu (Combobox, Listbox, Menu) opened from inside the dialog is
+ * portalled to `document.body`, so Radix sees a click on one of its options as a
+ * click outside the dialog and closes it mid-selection. Treat those clicks as
+ * inside.
+ */
+function isHeadlessUiPortalClick(event: PointerDownOutsideEvent) {
+  const target = event.target;
+  return (
+    target instanceof Element && !!target.closest("[data-headlessui-portal]")
+  );
+}
+
 /**
  * Based on https://github.com/tailwindlabs/headlessui/pull/1333/files#diff-d095a5f3fa3ad7f5ff99576cb61e5d75a979a6b7d5557f8a092f5d5c8c0c34deR49
  */