diff --git a/src/ImageSharp.Drawing/Shapes/OutlinePathExtensions.cs b/src/ImageSharp.Drawing/Shapes/OutlinePathExtensions.cs
index c76b7811..21e499a3 100644
--- a/src/ImageSharp.Drawing/Shapes/OutlinePathExtensions.cs
+++ b/src/ImageSharp.Drawing/Shapes/OutlinePathExtensions.cs
@@ -15,6 +15,31 @@ public static class OutlinePathExtensions
     private const JointStyle DefaultJointStyle = JointStyle.Square;
     private const EndCapStyle DefaultEndCapStyle = EndCapStyle.Butt;
 
+    /// <summary>
+    /// Calculates the scaling matrixes tha tmust be applied to the inout and output paths of for successful clipping.
+    /// </summary>
+    /// <param name="width">the requested width</param>
+    /// <param name="scaleUpMartrix">The matrix to apply to the input path</param>
+    /// <param name="scaleDownMartrix">The matrix to apply to the output path</param>
+    /// <returns>The final width to use internally to outlining</returns>
+    private static float CalculateScalingMatrix(float width, out Matrix3x2 scaleUpMartrix, out Matrix3x2 scaleDownMartrix)
+    {
+        // when the thickness is below a 0.5 threshold we need to scale
+        // the source path (up) and result path (down) by a factor to ensure
+        // the offest is greater than 0.5 to ensure offsetting isn't skipped.
+        scaleUpMartrix = Matrix3x2.Identity;
+        scaleDownMartrix = Matrix3x2.Identity;
+        if (width < 0.5)
+        {
+            float scale = 1 / width;
+            scaleUpMartrix = Matrix3x2.CreateScale(scale);
+            scaleDownMartrix = Matrix3x2.CreateScale(width);
+            width = 1;
+        }
+
+        return width;
+    }
+
     /// <summary>
     /// Generates an outline of the path.
     /// </summary>
@@ -41,10 +66,14 @@ public static IPath GenerateOutline(this IPath path, float width, JointStyle joi
             return Path.Empty;
         }
 
+        width = CalculateScalingMatrix(width, out Matrix3x2 scaleUpMartrix, out Matrix3x2 scaleDownMartrix);
+
         ClipperOffset offset = new(MiterOffsetDelta);
-        offset.AddPath(path, jointStyle, endCapStyle);
 
-        return offset.Execute(width);
+        // transform is noop for Matrix3x2.Identity
+        offset.AddPath(path.Transform(scaleUpMartrix), jointStyle, endCapStyle);
+
+        return offset.Execute(width).Transform(scaleDownMartrix);
     }
 
     /// <summary>
@@ -106,7 +135,9 @@ public static IPath GenerateOutline(this IPath path, float width, ReadOnlySpan<f
             return path.GenerateOutline(width, jointStyle, endCapStyle);
         }
 
-        IEnumerable<ISimplePath> paths = path.Flatten();
+        width = CalculateScalingMatrix(width, out Matrix3x2 scaleUpMartrix, out Matrix3x2 scaleDownMartrix);
+
+        IEnumerable<ISimplePath> paths = path.Transform(scaleUpMartrix).Flatten();
 
         ClipperOffset offset = new(MiterOffsetDelta);
         List<PointF> buffer = new();
@@ -186,6 +217,6 @@ public static IPath GenerateOutline(this IPath path, float width, ReadOnlySpan<f
             }
         }
 
-        return offset.Execute(width);
+        return offset.Execute(width).Transform(scaleDownMartrix);
     }
 }
diff --git a/tests/ImageSharp.Drawing.Tests/Issues/Issue_323.cs b/tests/ImageSharp.Drawing.Tests/Issues/Issue_323.cs
new file mode 100644
index 00000000..af8bae86
--- /dev/null
+++ b/tests/ImageSharp.Drawing.Tests/Issues/Issue_323.cs
@@ -0,0 +1,54 @@
+// Copyright (c) Six Labors.
+// Licensed under the Six Labors Split License.
+
+using SixLabors.ImageSharp.Drawing.Processing;
+using SixLabors.ImageSharp.PixelFormats;
+
+namespace SixLabors.ImageSharp.Drawing.Tests.Issues;
+
+public class Issue_323
+{
+    [Theory]
+    [WithSolidFilledImages(300, 300, "White", PixelTypes.Rgba32, 3f)]
+    [WithSolidFilledImages(300, 300, "White", PixelTypes.Rgba32, 1f)]
+    [WithSolidFilledImages(300, 300, "White", PixelTypes.Rgba32, 0.3f)]
+    [WithSolidFilledImages(300, 300, "White", PixelTypes.Rgba32, 0.7f)]
+    [WithSolidFilledImages(300, 300, "White", PixelTypes.Rgba32, 0.003f)]
+    public void DrawPolygonMustDrawoutlineOnly<TPixel>(TestImageProvider<TPixel> provider, float scale)
+        where TPixel : unmanaged, IPixel<TPixel>
+    {
+        Color color = Color.RebeccaPurple;
+        provider.RunValidatingProcessorTest(
+            x => x.DrawPolygon(
+                color,
+                scale,
+                new PointF[] {
+                    new(5, 5),
+                    new(5, 150),
+                    new(190, 150),
+                }),
+            new { scale });
+    }
+
+    [Theory]
+    [WithSolidFilledImages(300, 300, "White", PixelTypes.Rgba32, 3f)]
+    [WithSolidFilledImages(300, 300, "White", PixelTypes.Rgba32, 1f)]
+    [WithSolidFilledImages(300, 300, "White", PixelTypes.Rgba32, 0.3f)]
+    [WithSolidFilledImages(300, 300, "White", PixelTypes.Rgba32, 0.7f)]
+    [WithSolidFilledImages(300, 300, "White", PixelTypes.Rgba32, 0.003f)]
+    public void DrawPolygonMustDrawoutlineOnly_Pattern<TPixel>(TestImageProvider<TPixel> provider, float scale)
+        where TPixel : unmanaged, IPixel<TPixel>
+    {
+        Color color = Color.RebeccaPurple;
+        var pen = Pens.DashDot(color, scale);
+        provider.RunValidatingProcessorTest(
+                    x => x.DrawPolygon(
+                      pen,
+                      new PointF[] {
+                            new(5, 5),
+                            new(5, 150),
+                            new(190, 150),
+                        }),
+                    new { scale });
+    }
+}
diff --git a/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Pattern_Rgba32_Solid300x300_(255,255,255,255)_scale-0.003.png b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Pattern_Rgba32_Solid300x300_(255,255,255,255)_scale-0.003.png
new file mode 100644
index 00000000..1770f151
--- /dev/null
+++ b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Pattern_Rgba32_Solid300x300_(255,255,255,255)_scale-0.003.png
@@ -0,0 +1,3 @@
+version https://git-lfs.github.com/spec/v1
+oid sha256:bc86c51ad4946fb8a314c8d869a83cc2496d30468036729c3827c2c121cae69c
+size 1068
diff --git a/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Pattern_Rgba32_Solid300x300_(255,255,255,255)_scale-0.3.png b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Pattern_Rgba32_Solid300x300_(255,255,255,255)_scale-0.3.png
new file mode 100644
index 00000000..a60e0771
--- /dev/null
+++ b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Pattern_Rgba32_Solid300x300_(255,255,255,255)_scale-0.3.png
@@ -0,0 +1,3 @@
+version https://git-lfs.github.com/spec/v1
+oid sha256:62f86685f6f2326e629b8b84340bb1b3cbcf6ffe75facff0931b613337772345
+size 3296
diff --git a/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Pattern_Rgba32_Solid300x300_(255,255,255,255)_scale-0.7.png b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Pattern_Rgba32_Solid300x300_(255,255,255,255)_scale-0.7.png
new file mode 100644
index 00000000..5bf6378e
--- /dev/null
+++ b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Pattern_Rgba32_Solid300x300_(255,255,255,255)_scale-0.7.png
@@ -0,0 +1,3 @@
+version https://git-lfs.github.com/spec/v1
+oid sha256:534d3fece38b94386b6ba20aa121addda1beea61d38cb34b9d2ae09b662fd38b
+size 3585
diff --git a/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Pattern_Rgba32_Solid300x300_(255,255,255,255)_scale-1.png b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Pattern_Rgba32_Solid300x300_(255,255,255,255)_scale-1.png
new file mode 100644
index 00000000..61df79c3
--- /dev/null
+++ b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Pattern_Rgba32_Solid300x300_(255,255,255,255)_scale-1.png
@@ -0,0 +1,3 @@
+version https://git-lfs.github.com/spec/v1
+oid sha256:4fff4ab1fec04c432529fd67d9c50934ce083fa6e7c0c4432fd6520eac2e53ac
+size 3625
diff --git a/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Pattern_Rgba32_Solid300x300_(255,255,255,255)_scale-3.png b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Pattern_Rgba32_Solid300x300_(255,255,255,255)_scale-3.png
new file mode 100644
index 00000000..d5630da2
--- /dev/null
+++ b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Pattern_Rgba32_Solid300x300_(255,255,255,255)_scale-3.png
@@ -0,0 +1,3 @@
+version https://git-lfs.github.com/spec/v1
+oid sha256:92a356847e8aa36b361a2208021a0c0e2a3287d615f0b948bdbcc0bc3b336bc4
+size 4300
diff --git a/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Rgba32_Solid300x300_(255,255,255,255)_scale-0.003.png b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Rgba32_Solid300x300_(255,255,255,255)_scale-0.003.png
new file mode 100644
index 00000000..924d09bf
--- /dev/null
+++ b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Rgba32_Solid300x300_(255,255,255,255)_scale-0.003.png
@@ -0,0 +1,3 @@
+version https://git-lfs.github.com/spec/v1
+oid sha256:8b02efd026d5ed83d1e0e747c8675d340bda7ba246d5a9385ecc6dabc81861e0
+size 3015
diff --git a/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Rgba32_Solid300x300_(255,255,255,255)_scale-0.3.png b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Rgba32_Solid300x300_(255,255,255,255)_scale-0.3.png
new file mode 100644
index 00000000..e6b9aee3
--- /dev/null
+++ b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Rgba32_Solid300x300_(255,255,255,255)_scale-0.3.png
@@ -0,0 +1,3 @@
+version https://git-lfs.github.com/spec/v1
+oid sha256:f02d5a40abd8bbef39f2648f2d40d5da5a28adfbc5b015a56641eef5fb50de05
+size 3050
diff --git a/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Rgba32_Solid300x300_(255,255,255,255)_scale-0.7.png b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Rgba32_Solid300x300_(255,255,255,255)_scale-0.7.png
new file mode 100644
index 00000000..8f585eb2
--- /dev/null
+++ b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Rgba32_Solid300x300_(255,255,255,255)_scale-0.7.png
@@ -0,0 +1,3 @@
+version https://git-lfs.github.com/spec/v1
+oid sha256:11b915b55e0005b52bf80e4891f293b6cb6477f3e0d83fead71768ac359fa610
+size 3382
diff --git a/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Rgba32_Solid300x300_(255,255,255,255)_scale-1.png b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Rgba32_Solid300x300_(255,255,255,255)_scale-1.png
new file mode 100644
index 00000000..79f87092
--- /dev/null
+++ b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Rgba32_Solid300x300_(255,255,255,255)_scale-1.png
@@ -0,0 +1,3 @@
+version https://git-lfs.github.com/spec/v1
+oid sha256:8a48c33c58c36ba7f581fe7d60eaf0bbc96948640b14ccbdd891adeae031a7ad
+size 3691
diff --git a/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Rgba32_Solid300x300_(255,255,255,255)_scale-3.png b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Rgba32_Solid300x300_(255,255,255,255)_scale-3.png
new file mode 100644
index 00000000..7b5c2352
--- /dev/null
+++ b/tests/Images/ReferenceOutput/Issue_323/DrawPolygonMustDrawoutlineOnly_Rgba32_Solid300x300_(255,255,255,255)_scale-3.png
@@ -0,0 +1,3 @@
+version https://git-lfs.github.com/spec/v1
+oid sha256:e80954c53985fc65b0846778861e3c023a8c798d466be887545fe2438ab5e3a3
+size 4353