diff --git a/flake.nix b/flake.nix
index d5379375e..1c205a5b9 100644
--- a/flake.nix
+++ b/flake.nix
@@ -47,6 +47,7 @@
               cmakeFlags = [
                 "-DMANIFOLD_PYBIND=ON"
                 "-DMANIFOLD_CBIND=ON"
+                "-DMANIFOLD_DEBUG=ON"
                 "-DMANIFOLD_EXPORT=ON"
                 "-DBUILD_SHARED_LIBS=ON"
                 "-DMANIFOLD_PAR=${pkgs.lib.strings.toUpper parallel-backend}"
diff --git a/test/boolean_complex_test.cpp b/test/boolean_complex_test.cpp
index 73622c184..4da3842e0 100644
--- a/test/boolean_complex_test.cpp
+++ b/test/boolean_complex_test.cpp
@@ -262,6 +262,92 @@ TEST(BooleanComplex, Spiral) {
   EXPECT_EQ(result.Genus(), -120);
 }
 
+TEST(BooleanComplex, TriangulationFail) {
+  // clang-format off
+  MeshGL m;
+  m.vertProperties = {
+    0.75, -1, -1, //
+    0.75, -1, -0.25, //
+    0.75, -0.667, 0.083, //
+    0.75, -0.25, -1, //
+    0.75, 0.083, -0.667, //
+    0.833, 0.5, -0.167, //
+    0.75, 0.0417, 0.0417, //
+    0.75, 0.5, 0.25, //
+    0.75, 0.25, 0.5, //
+    1.25, -1, -1, //
+    1.25, -1, -0.75, //
+    1.25, -1, -0.75, //
+    1.25, -0.75, -1, //
+    1, -0.5, 0, //
+    1, -0.25, -0.25, //
+    1, 0, -0.5, //
+    1.25, 0.5, 0.25, //
+    1.25, 0.5, 0.75};
+  m.triVerts = {
+    1, 6, 0, //
+    3, 0, 6, //
+    0, 10, 1, //
+    0, 3, 12, //
+    1, 13, 2, //
+    6, 1, 2, //
+    13, 8, 2, //
+    15, 3, 4, //
+    4, 3, 6, //
+    15, 4, 7, //
+    5, 15, 7, //
+    6, 2, 8, //
+    6, 14, 7, //
+    8, 14, 6, //
+    7, 4, 6, //
+    13, 14, 8, //
+    5, 7, 16, //
+    0, 9, 10, //
+    9, 0, 12, //
+    1, 10, 13, //
+    12, 3, 15, //
+    13, 10, 14, //
+    11, 7, 12, //
+    12, 14, 10, //
+    10, 9, 12, //
+    17, 11, 12, //
+    14, 12, 7, //
+    15, 5, 16, //
+    16, 12, 15, //
+    7, 11, 17, //
+    7, 17, 16, //
+    12, 16, 17};
+  MeshGL m2;
+  m2.vertProperties = {
+    0.75, 0, 0.75, //
+    0.75, 0.25, 0.5, //
+    1.25, -1, -0.75, //
+    1.25, -0.75, -1, //
+    1, 0.5, 0.5, //
+    1.25, 0.5, 0.25, //
+    1.25, 0.5, 0.75};
+  m2.triVerts = {
+    4, 1, 0, //
+    3, 0, 1, //
+    0, 3, 2, //
+    3, 6, 2, //
+    0, 2, 6, //
+    3, 1, 5, //
+    1, 4, 5, //
+    4, 0, 6, //
+    3, 5, 6, //
+    4, 6, 5};
+  // clang-format on
+
+#ifdef MANIFOLD_EXPORT
+  if (options.exportModels)
+    ExportMesh("trifail.glb",
+               Manifold::Compose({Manifold(m), Manifold(m2)}).GetMeshGL(), {});
+#endif
+
+  auto gl = (Manifold(m) + Manifold(m2)).GetMeshGL();
+}
+
 #ifdef MANIFOLD_CROSS_SECTION
 TEST(BooleanComplex, Sweep) {
   PolygonParams().processOverlaps = true;