diff --git a/crates/engine/src/tests.rs b/crates/engine/src/tests.rs
index d1ce63f5d..7a417ab29 100644
--- a/crates/engine/src/tests.rs
+++ b/crates/engine/src/tests.rs
@@ -986,6 +986,53 @@ fn ungrouping_nested_groups_in_any_order_returns_only_freed_shapes() {
     assert_eq!(order, [sid(a), sid(b), sid(c), sid(d), sid(e)]);
 }
 
+/// Ungrouping a top-level group and a group inside it in one call frees the shapes of both onto
+/// the slide, in the top-level group's place and drawn where they were, whichever is named first.
+#[test]
+fn ungrouping_a_top_level_group_with_a_group_inside_it_frees_both() {
+    fn rect(s: &mut Session, x: f64, y: f64) -> u64 {
+        s.execute("shape.insert", &json!({"preset": "rect", "rect": [x, y, 100, 100]})).unwrap()["id"].as_u64().unwrap()
+    }
+    fn group(s: &mut Session, ids: [u64; 2]) -> u64 {
+        s.execute("arrange.group", &json!({"ids": ids})).unwrap()["id"].as_u64().unwrap()
+    }
+    let sid = |id: u64| ShapeId(u32::try_from(id).unwrap());
+    let sites = |s: &Session, id: u64| {
+        let st = s.doc().unwrap();
+        connect::sites_of(&st.doc, &st.selection, st.shapes(), sid(id)).unwrap()
+    };
+    let roots = |s: &Session| -> Vec<ShapeId> { s.doc().unwrap().shapes().iter().map(|x| x.id).collect() };
+    for outer_first in [true, false] {
+        let mut s = session();
+        s.execute("slide.new", &json!({"layout": "blank"})).unwrap();
+        let [a, b, c, z] = [(100.0, 100.0), (300.0, 100.0), (100.0, 300.0), (500.0, 500.0)].map(|(x, y)| rect(&mut s, x, y));
+        let inner = group(&mut s, [a, b]);
+        let outer = group(&mut s, [inner, c]);
+        s.execute("shape.resize", &json!({"ids": [outer], "w": 600})).unwrap();
+        let before = [a, b, c].map(|id| sites(&s, id));
+        let freed = [sid(a), sid(b), sid(c)];
+        let mut expected = vec![];
+        for x in roots(&s) {
+            if x == sid(outer) {
+                expected.extend(freed);
+            } else {
+                expected.push(x);
+            }
+        }
+        assert!(expected.contains(&sid(z)));
+        let ids = if outer_first { [outer, inner] } else { [inner, outer] };
+        let r = s.execute("arrange.ungroup", &json!({"ids": ids})).unwrap();
+        assert_eq!(r["ids"], json!([a, b, c]), "{ids:?}");
+        assert_eq!(s.doc().unwrap().selection.shapes, freed, "{ids:?}");
+        assert_eq!(roots(&s), expected, "{ids:?}");
+        for (id, was) in [a, b, c].into_iter().zip(before) {
+            let now = sites(&s, id);
+            assert_eq!(was.len(), now.len(), "{ids:?}: shape {id}");
+            assert!(was.iter().zip(&now).all(|(p, q)| (*p - *q).hypot() < 1e-6), "{ids:?}: shape {id} moved from {was:?} to {now:?}");
+        }
+    }
+}
+
 /// Grouping a group again and again stops at `MAX_GROUP_DEPTH`: past about 39 levels a saved
 /// .deckcraft file no longer opens, and past 64 commands such as format.languageAll miss the text.
 #[test]