diff --git a/src/ImageSharp/Drawing/Paths/InternalPath.cs b/src/ImageSharp/Drawing/Paths/InternalPath.cs
index b34702253..52d43b6e8 100644
--- a/src/ImageSharp/Drawing/Paths/InternalPath.cs
+++ b/src/ImageSharp/Drawing/Paths/InternalPath.cs
@@ -60,10 +60,28 @@ namespace ImageSharp.Drawing.Paths
         /// <param name="segments">The segments.</param>
         /// <param name="isClosedPath">if set to <c>true</c> [is closed path].</param>
         internal InternalPath(ILineSegment[] segments, bool isClosedPath)
+            : this(Simplify(segments), isClosedPath)
         {
-            Guard.NotNull(segments, nameof(segments));
+        }
 
-            this.points = this.Simplify(segments);
+        /// <summary>
+        /// Initializes a new instance of the <see cref="InternalPath" /> class.
+        /// </summary>
+        /// <param name="segment">The segment.</param>
+        /// <param name="isClosedPath">if set to <c>true</c> [is closed path].</param>
+        internal InternalPath(ILineSegment segment, bool isClosedPath)
+            : this(segment.AsSimpleLinearPath(), isClosedPath)
+        {
+        }
+
+        /// <summary>
+        /// Initializes a new instance of the <see cref="InternalPath" /> class.
+        /// </summary>
+        /// <param name="points">The points.</param>
+        /// <param name="isClosedPath">if set to <c>true</c> [is closed path].</param>
+        internal InternalPath(Vector2[] points, bool isClosedPath)
+        {
+            this.points = points;
             this.closedPath = isClosedPath;
 
             float minX = this.points.Min(x => x.X);
@@ -192,7 +210,7 @@ namespace ImageSharp.Drawing.Paths
         /// <returns>
         /// The <see cref="T:Vector2[]"/>.
         /// </returns>
-        private Vector2[] Simplify(ILineSegment[] segments)
+        private static Vector2[] Simplify(ILineSegment[] segments)
         {
             List<Vector2> simplified = new List<Vector2>();
             foreach (ILineSegment seg in segments)
diff --git a/src/ImageSharp/Drawing/Shapes/ComplexPolygon.cs b/src/ImageSharp/Drawing/Shapes/ComplexPolygon.cs
index d0edb76aa..d42cae872 100644
--- a/src/ImageSharp/Drawing/Shapes/ComplexPolygon.cs
+++ b/src/ImageSharp/Drawing/Shapes/ComplexPolygon.cs
@@ -20,8 +20,7 @@ namespace ImageSharp.Drawing.Shapes
     public sealed class ComplexPolygon : IShape
     {
         private const float ClipperScaleFactor = 100f;
-        private IEnumerable<IShape> holes;
-        private IEnumerable<IShape> outlines;
+        private IShape[] shapes;
         private IEnumerable<IPath> paths;
 
         /// <summary>
@@ -39,17 +38,17 @@ namespace ImageSharp.Drawing.Shapes
         /// </summary>
         /// <param name="outlines">The outlines.</param>
         /// <param name="holes">The holes.</param>
-        public ComplexPolygon(IEnumerable<IShape> outlines, IEnumerable<IShape> holes)
+        public ComplexPolygon(IShape[] outlines, IShape[] holes)
         {
             Guard.NotNull(outlines, nameof(outlines));
-            Guard.MustBeGreaterThanOrEqualTo(outlines.Count(), 1, nameof(outlines));
+            Guard.MustBeGreaterThanOrEqualTo(outlines.Length, 1, nameof(outlines));
 
             this.FixAndSetShapes(outlines, holes);
 
-            var minX = outlines.Min(x => x.Bounds.Left);
-            var maxX = outlines.Max(x => x.Bounds.Right);
-            var minY = outlines.Min(x => x.Bounds.Top);
-            var maxY = outlines.Max(x => x.Bounds.Bottom);
+            var minX = this.shapes.Min(x => x.Bounds.Left);
+            var maxX = this.shapes.Max(x => x.Bounds.Right);
+            var minY = this.shapes.Min(x => x.Bounds.Top);
+            var maxY = this.shapes.Max(x => x.Bounds.Bottom);
 
             this.Bounds = new RectangleF(minX, minY, maxX - minX, maxY - minY);
         }
@@ -69,30 +68,37 @@ namespace ImageSharp.Drawing.Shapes
         /// <returns>
         /// Returns the distance from thr shape to the point
         /// </returns>
+        /// <remarks>
+        /// Due to the clipping we did during construction we know that out shapes do not overlap at there edges
+        /// therefore for apoint to be in more that one we must be in a hole of another, theoretically this could
+        /// then flip again to be in a outlin inside a hole inside an outline :)
+        /// </remarks>
         float IShape.Distance(Vector2 point)
         {
-            // get the outline we are closest to the center of
-            // by rights we should only be inside 1 outline
-            // othersie we will start returning the distanct to the nearest shape
-            var dist = this.outlines.Select(o => o.Distance(point)).OrderBy(p => p).First();
-
-            if (dist <= 0)
+            float dist = float.MaxValue;
+            bool inside = false;
+            foreach (IShape shape in this.shapes)
             {
-                // inside poly
-                foreach (var hole in this.holes)
+                var d = shape.Distance(point);
+
+                if (d <= 0)
                 {
-                    var distFromHole = hole.Distance(point);
+                    // we are inside a poly
+                    d = -d;  // flip the sign
+                    inside ^= true; // flip the inside flag
+                }
 
-                    // less than zero we are inside shape
-                    if (distFromHole <= 0)
-                    {
-                        // invert distance
-                        dist = distFromHole * -1;
-                        break;
-                    }
+                if (d < dist)
+                {
+                    dist = d;
                 }
             }
 
+            if (inside)
+            {
+                return -dist;
+            }
+
             return dist;
         }
 
@@ -138,59 +144,136 @@ namespace ImageSharp.Drawing.Shapes
             }
         }
 
-        private void AddPoints(ClipperLib.Clipper clipper, IEnumerable<IShape> shapes, ClipperLib.PolyType polyType)
+        private void AddPoints(ClipperLib.Clipper clipper, IShape[] shapes, bool[] shouldInclude, ClipperLib.PolyType polyType)
         {
-            foreach (var shape in shapes)
+            for (var i = 0; i < shapes.Length; i++)
             {
-                this.AddPoints(clipper, shape, polyType);
+                if (shouldInclude[i])
+                {
+                    this.AddPoints(clipper, shapes[i], polyType);
+                }
             }
         }
 
-        private void ExtractOutlines(ClipperLib.PolyNode tree, List<Polygon> outlines, List<Polygon> holes)
+        private void ExtractOutlines(ClipperLib.PolyNode tree, List<IShape> shapes)
         {
             if (tree.Contour.Any())
             {
                 // convert the Clipper Contour from scaled ints back down to the origional size (this is going to be lossy but not significantly)
-                var polygon = new Polygon(new LinearLineSegment(tree.Contour.Select(x => new Vector2(x.X / ClipperScaleFactor, x.Y / ClipperScaleFactor)).ToArray()));
-
-                if (tree.IsHole)
+                var pointCount = tree.Contour.Count;
+                var vectors = new Vector2[pointCount];
+                for (var i = 0; i < pointCount; i++)
                 {
-                    holes.Add(polygon);
-                }
-                else
-                {
-                    outlines.Add(polygon);
+                    var p = tree.Contour[i];
+                    vectors[i] = new Vector2(p.X, p.Y) / ClipperScaleFactor;
                 }
+
+                var polygon = new Polygon(new LinearLineSegment(vectors));
+
+                shapes.Add(polygon);
             }
 
             foreach (var c in tree.Childs)
             {
-                this.ExtractOutlines(c, outlines, holes);
+                this.ExtractOutlines(c, shapes);
             }
         }
 
-        private void FixAndSetShapes(IEnumerable<IShape> outlines, IEnumerable<IShape> holes)
+        /// <summary>
+        /// Determines if the <see cref="IShape"/>s bounding boxes overlap.
+        /// </summary>
+        /// <param name="source">The source.</param>
+        /// <param name="target">The target.</param>
+        /// <returns>true if the 2 shapes bounding boxes overlap.</returns>
+        private bool OverlappingBoundingBoxes(IShape source, IShape target)
+        {
+            return source.Bounds.Intersects(target.Bounds);
+        }
+
+        private void FixAndSetShapes(IShape[] outlines, IShape[] holes)
         {
-            var clipper = new ClipperLib.Clipper();
+            // if any outline doesn't overlap another shape then we don't have to bother with sending them through clipper
+            // as sending then though clipper will turn them into generic polygons and loose thier shape specific optimisations
+            int outlineLength = outlines.Length;
+            int holesLength = holes?.Length ?? 0;
+            bool[] overlappingOutlines = new bool[outlineLength];
+            bool[] overlappingHoles = new bool[holesLength];
+            bool anyOutlinesOverlapping = false;
+            bool anyHolesOverlapping = false;
+
+            for (int i = 0; i < outlineLength; i++)
+            {
+                for (int j = i + 1; j < outlineLength; j++)
+                {
+                    // skip the bounds check if they are already tested
+                    if (overlappingOutlines[i] == false || overlappingOutlines[j] == false)
+                    {
+                        if (this.OverlappingBoundingBoxes(outlines[i], outlines[j]))
+                        {
+                            overlappingOutlines[i] = true;
+                            overlappingOutlines[j] = true;
+                            anyOutlinesOverlapping = true;
+                        }
+                    }
+                }
+
+                for (int k = 0; k < holesLength; k++)
+                {
+                    if (overlappingOutlines[i] == false || overlappingHoles[k] == false)
+                    {
+                        if (this.OverlappingBoundingBoxes(outlines[i], holes[k]))
+                        {
+                            overlappingOutlines[i] = true;
+                            overlappingHoles[k] = true;
+                            anyOutlinesOverlapping = true;
+                            anyHolesOverlapping = true;
+                        }
+                    }
+                }
+            }
+
+            if (anyOutlinesOverlapping)
+            {
+                var clipper = new ClipperLib.Clipper();
+
+                // add the outlines and the holes to clipper, scaling up from the float source to the int based system clipper uses
+                this.AddPoints(clipper, outlines, overlappingOutlines, ClipperLib.PolyType.ptSubject);
+                if (anyHolesOverlapping)
+                {
+                    this.AddPoints(clipper, holes, overlappingHoles, ClipperLib.PolyType.ptClip);
+                }
+
+                var tree = new ClipperLib.PolyTree();
+                clipper.Execute(ClipperLib.ClipType.ctDifference, tree);
 
-            // add the outlines and the holes to clipper, scaling up from the float source to the int based system clipper uses
-            this.AddPoints(clipper, outlines, ClipperLib.PolyType.ptSubject);
-            this.AddPoints(clipper, holes, ClipperLib.PolyType.ptClip);
+                List<IShape> newShapes = new List<IShape>();
 
-            var tree = new ClipperLib.PolyTree();
-            clipper.Execute(ClipperLib.ClipType.ctDifference, tree);
+                // convert the 'tree' back to shapes
+                this.ExtractOutlines(tree, newShapes);
 
-            List<Polygon> newOutlines = new List<Polygon>();
-            List<Polygon> newHoles = new List<Polygon>();
+                // add the origional outlines that where not overlapping
+                for (int i = 0; i < outlineLength - 1; i++)
+                {
+                    if (!overlappingOutlines[i])
+                    {
+                        newShapes.Add(outlines[i]);
+                    }
+                }
 
-            // convert the 'tree' back to paths
-            this.ExtractOutlines(tree, newOutlines, newHoles);
+                this.shapes = newShapes.ToArray();
+            }
+            else
+            {
+                this.shapes = outlines;
+            }
 
-            this.outlines = newOutlines;
-            this.holes = newHoles;
+            var paths = new List<IPath>();
+            foreach (var o in this.shapes)
+            {
+                paths.AddRange(o);
+            }
 
-            // extract the final list of paths out of the new polygons we just converted down to.
-            this.paths = newOutlines.Union(newHoles).ToArray();
+            this.paths = paths;
         }
     }
 }
\ No newline at end of file
diff --git a/src/ImageSharp/Drawing/Shapes/Polygon.cs b/src/ImageSharp/Drawing/Shapes/Polygon.cs
index 9d9626d4e..6da27cf48 100644
--- a/src/ImageSharp/Drawing/Shapes/Polygon.cs
+++ b/src/ImageSharp/Drawing/Shapes/Polygon.cs
@@ -29,6 +29,16 @@ namespace ImageSharp.Drawing.Shapes
             this.pathCollection = new[] { this };
         }
 
+        /// <summary>
+        /// Initializes a new instance of the <see cref="Polygon" /> class.
+        /// </summary>
+        /// <param name="segment">The segment.</param>
+        public Polygon(ILineSegment segment)
+        {
+            this.innerPath = new InternalPath(segment, true);
+            this.pathCollection = new[] { this };
+        }
+
         /// <summary>
         /// Gets the bounding box of this shape.
         /// </summary>
@@ -98,8 +108,7 @@ namespace ImageSharp.Drawing.Shapes
         /// <summary>
         /// Calcualtes the distance along and away from the path for a specified point.
         /// </summary>
-        /// <param name="x">The x.</param>
-        /// <param name="y">The y.</param>
+        /// <param name="point">The point along the path.</param>
         /// <returns>
         /// distance metadata about the point.
         /// </returns>
diff --git a/tests/ImageSharp.Tests/Drawing/LineComplexPolygonTests.cs b/tests/ImageSharp.Tests/Drawing/LineComplexPolygonTests.cs
index 1f6708bf8..cdcb5ebe4 100644
--- a/tests/ImageSharp.Tests/Drawing/LineComplexPolygonTests.cs
+++ b/tests/ImageSharp.Tests/Drawing/LineComplexPolygonTests.cs
@@ -66,6 +66,55 @@ namespace ImageSharp.Tests.Drawing
             }
         }
 
+        [Fact]
+        public void ImageShouldBeOverlayedByPolygonOutlineNoOverlapping()
+        {
+            string path = CreateOutputDirectory("Drawing", "LineComplexPolygon");
+            var simplePath = new LinearPolygon(
+                            new Vector2(10, 10),
+                            new Vector2(200, 150),
+                            new Vector2(50, 300));
+
+            var hole1 = new LinearPolygon(
+                            new Vector2(207, 25),
+                            new Vector2(263, 25),
+                            new Vector2(235, 57));
+
+            var image = new Image(500, 500);
+
+            using (FileStream output = File.OpenWrite($"{path}/SimpleVanishHole.png"))
+            {
+                image
+                .BackgroundColor(Color.Blue)
+                .DrawPolygon(Color.HotPink, 5, new ComplexPolygon(simplePath, hole1))
+                .Save(output);
+            }
+
+            using (var sourcePixels = image.Lock())
+            {
+                Assert.Equal(Color.HotPink, sourcePixels[10, 10]);
+
+                Assert.Equal(Color.HotPink, sourcePixels[200, 150]);
+
+                Assert.Equal(Color.HotPink, sourcePixels[50, 300]);
+
+
+                //Assert.Equal(Color.HotPink, sourcePixels[37, 85]);
+
+                //Assert.Equal(Color.HotPink, sourcePixels[93, 85]);
+
+                //Assert.Equal(Color.HotPink, sourcePixels[65, 137]);
+
+                Assert.Equal(Color.Blue, sourcePixels[2, 2]);
+
+                //inside hole
+                Assert.Equal(Color.Blue, sourcePixels[57, 99]);
+
+                //inside shape
+                Assert.Equal(Color.Blue, sourcePixels[100, 192]);
+            }
+        }
+
 
         [Fact]
         public void ImageShouldBeOverlayedByPolygonOutlineOverlapping()