diff --git a/src/scene/entity.rs b/src/scene/entity.rs
index 011839528..bf2cfd239 100644
--- a/src/scene/entity.rs
+++ b/src/scene/entity.rs
@@ -1655,13 +1655,26 @@ impl Scene {
         // the outer boundary from its holes with NaN sentinels in
         // `boundary_wcs`; split on those so nested hatches (e.g. a small
         // rectangle inside a big one) persist with real holes instead of a
-        // single self-intersecting polyline.
+        // single self-intersecting polyline. Only the FIRST ring carries the
+        // external / outermost flags — every later ring is a hole and must not
+        // be flagged external, or DXF/DWG consumers treat the inner loop as
+        // another outer island rather than a hole.
         if let Some(wcs) = &model.boundary_wcs {
             let mut ring: Vec<Vector2> = Vec::new();
-            let mut push_ring = |r: &mut Vec<Vector2>| {
+            let mut first = true;
+            let mut push_ring = |r: &mut Vec<Vector2>, is_outer: bool| {
                 if !r.is_empty() {
                     let edge = PolylineEdge::new(std::mem::take(r), true);
-                    let mut path = BoundaryPath::external();
+                    let mut path = if is_outer {
+                        let mut p = BoundaryPath::external();
+                        p.flags = acadrust::entities::hatch::BoundaryPathFlags::from_bits(
+                            p.flags.bits()
+                                | acadrust::entities::hatch::BoundaryPathFlags::OUTERMOST.bits(),
+                        );
+                        p
+                    } else {
+                        BoundaryPath::new()
+                    };
                     path.add_edge(BoundaryEdge::Polyline(edge));
                     dxf.paths.push(path);
                 }
@@ -1670,10 +1683,12 @@ impl Scene {
                 if x.is_finite() && y.is_finite() {
                     ring.push(Vector2::new(x, y));
                 } else {
-                    push_ring(&mut ring);
+                    let is_outer = first;
+                    first = false;
+                    push_ring(&mut ring, is_outer);
                 }
             }
-            push_ring(&mut ring);
+            push_ring(&mut ring, first);
         }
         if dxf.paths.is_empty() {
             let wx = model.world_origin[0];
diff --git a/tests/block_hatch_export.rs b/tests/block_hatch_export.rs
index 234b3d5e5..79d8e663e 100644
--- a/tests/block_hatch_export.rs
+++ b/tests/block_hatch_export.rs
@@ -266,3 +266,57 @@ fn app_created_hatch_roundtrips_catalog_spacing() {
          — build_dxf_pattern must store the world-frame offset, not the local step"
     );
 }
+
+// Regression: a picked "big minus small" hatch must serialize the outer ring
+// with the external / outermost flags and each hole ring WITHOUT them. If every
+// NaN-separated ring were flagged external, DXF/DWG consumers would treat the
+// inner loop as another outer island instead of a hole.
+#[test]
+fn nested_hatch_serializes_only_outer_as_external() {
+    use std::sync::Arc;
+
+    use OpenCADStudio::scene::model::hatch_model::HatchModel;
+
+    let outer: Vec<[f64; 2]> = vec![[-10.0, -10.0], [10.0, -10.0], [10.0, 10.0], [-10.0, 10.0]];
+    let hole: Vec<[f64; 2]> = vec![[-5.0, -5.0], [5.0, -5.0], [5.0, 5.0], [-5.0, 5.0]];
+
+    // Outer boundary + hole, NaN-separated, exactly as the HATCH command packs
+    // them in `boundary_wcs`.
+    let mut wcs: Vec<[f64; 2]> = outer.clone();
+    wcs.push([f64::NAN, f64::NAN]);
+    wcs.extend(hole.iter().copied());
+
+    let boundary_f32: Vec<[f32; 2]> = wcs.iter().map(|&[x, y]| [x as f32, y as f32]).collect();
+
+    let model = HatchModel {
+        world_origin: [0.0, 0.0],
+        boundary: Arc::new(boundary_f32),
+        boundary_wcs: Some(Arc::new(wcs)),
+        pattern: HatchPattern::Solid,
+        name: "SOLID".into(),
+        color: [0.45, 0.45, 0.45, 0.60],
+        angle_offset: 0.0,
+        scale: 1.0,
+        vp_scissor: None,
+        draw_depth: 0.0,
+    };
+
+    let mut scene = Scene::new();
+    scene.add_hatch(model);
+
+    let dxf = scene
+        .document
+        .entities()
+        .find_map(|e| if let EntityType::Hatch(h) = e { Some(h) } else { None })
+        .expect("nested hatch written to document");
+
+    assert_eq!(dxf.paths.len(), 2, "outer boundary + one hole path");
+
+    let ex = BoundaryPathFlags::EXTERNAL.bits();
+    let out = BoundaryPathFlags::OUTERMOST.bits();
+
+    assert!(dxf.paths[0].flags.bits() & ex != 0, "outer path must be flagged external");
+    assert!(dxf.paths[0].flags.bits() & out != 0, "outer path must be flagged outermost");
+    assert!(dxf.paths[1].flags.bits() & ex == 0, "hole path must NOT be flagged external");
+    assert!(dxf.paths[1].flags.bits() & out == 0, "hole path must NOT be flagged outermost");
+}