diff --git a/OpenNest.Core/Geometry/Circle.cs b/OpenNest.Core/Geometry/Circle.cs
index dd0148f..05a03de 100644
--- a/OpenNest.Core/Geometry/Circle.cs
+++ b/OpenNest.Core/Geometry/Circle.cs
@@ -137,7 +137,9 @@ namespace OpenNest.Geometry
         public List<Vector> ToPoints(int segments = 1000, bool circumscribe = false)
         {
             var points = new List<Vector>();
-            var stepAngle = Angle.TwoPI / segments;
+            var stepAngle = Rotation == RotationType.CW
+                ? -Angle.TwoPI / segments
+                : Angle.TwoPI / segments;
 
             var r = circumscribe && segments > 0
                 ? Radius / System.Math.Cos(stepAngle / 2.0)
diff --git a/OpenNest.Tests/Geometry/ContourClassificationTests.cs b/OpenNest.Tests/Geometry/ContourClassificationTests.cs
index 5dae382..593b46a 100644
--- a/OpenNest.Tests/Geometry/ContourClassificationTests.cs
+++ b/OpenNest.Tests/Geometry/ContourClassificationTests.cs
@@ -154,4 +154,18 @@ public class ContourClassificationTests
 
         Assert.NotEqual(originalDirection, newDirection);
     }
+
+    [Fact]
+    public void Reverse_changes_direction_label_for_circle()
+    {
+        var shape = MakeCircleShape(0, 0, 10);
+        var contours = ContourInfo.Classify(new List<Shape> { shape });
+        var contour = contours[0];
+
+        var originalDirection = contour.DirectionLabel;
+        contour.Reverse();
+        var newDirection = contour.DirectionLabel;
+
+        Assert.NotEqual(originalDirection, newDirection);
+    }
 }