diff --git a/src/specify_cli/workflows/overlays/merge.py b/src/specify_cli/workflows/overlays/merge.py
index 5521b10a76..bf28a1f133 100644
--- a/src/specify_cli/workflows/overlays/merge.py
+++ b/src/specify_cli/workflows/overlays/merge.py
@@ -292,9 +292,21 @@ def _traverse_and_apply(
                         cases[case_key] = _traverse_and_apply(case_steps, edits_by_anchor, sources)
             result.append(step)
 
-        # Insert after (highest priority closest to anchor — reversed merge order).
-        for layer, edit in reversed(edits):
-            if edit.operation == "insert_after":
+        # Insert after: higher-priority overlays land closer to the anchor
+        # (reversed merge order), but a single overlay's own inserts must keep
+        # their declared order — mirroring the forward insert_before loop above.
+        # Reversing the whole flat list would also flip an overlay's own edits,
+        # so group contiguous same-layer edits and reverse the GROUP order only.
+        after_groups: list[list[tuple[OverlayLayer, OverlayEdit]]] = []
+        for layer, edit in edits:
+            if edit.operation != "insert_after":
+                continue
+            if after_groups and after_groups[-1][0][0] is layer:
+                after_groups[-1].append((layer, edit))
+            else:
+                after_groups.append([(layer, edit)])
+        for group in reversed(after_groups):
+            for layer, edit in group:
                 new_step = copy.deepcopy(edit.step)
                 _record_sources_recursively(new_step, layer.source, sources)
                 result.append(new_step)
diff --git a/tests/workflows/test_overlay_merge.py b/tests/workflows/test_overlay_merge.py
index 17790d6801..c924d1c271 100644
--- a/tests/workflows/test_overlay_merge.py
+++ b/tests/workflows/test_overlay_merge.py
@@ -162,6 +162,23 @@ def test_merge_steps_higher_priority_wins(self):
             ComposedStep("low-step", "project:low"),
         ]
 
+    def test_merge_steps_multiple_insert_after_same_overlay_preserves_order(self):
+        # Two insert_after edits from ONE overlay on the same anchor must keep
+        # their declared order (a, x, y, b) — mirroring insert_before. The old
+        # reversed(edits) over the flat list flipped them to (a, y, x, b).
+        base = [_step("a"), _step("b")]
+        overlay = Overlay(
+            id="ov1",
+            extends="wf",
+            priority=10,
+            edits=[
+                OverlayEdit("insert_after", "a", _step("x")),
+                OverlayEdit("insert_after", "a", _step("y")),
+            ],
+        )
+        steps, _ = merge_steps(base, [_layer(overlay, "project:ov1")])
+        assert [s["id"] for s in steps] == ["a", "x", "y", "b"]
+
     def test_merge_steps_replace_wins_over_insert(self):
         """Overlays apply to the original tree only; targeting an overlay-introduced step raises."""
         base = [_step("a")]