diff --git a/src/SixLabors.Fonts/TextLayout.cs b/src/SixLabors.Fonts/TextLayout.cs
index 46137fcb..f137cd81 100644
--- a/src/SixLabors.Fonts/TextLayout.cs
+++ b/src/SixLabors.Fonts/TextLayout.cs
@@ -1223,7 +1223,11 @@ VerticalOrientationType.Rotate or
                                     // If the line is too long, insert a forced line break.
                                     if (textLine.ScaledLineAdvance > wrappingLength)
                                     {
-                                        remaining.InsertAt(0, textLine.SplitAt(wrappingLength));
+                                        TextLine overflow = textLine.SplitAt(wrappingLength);
+                                        if (overflow != textLine)
+                                        {
+                                            remaining.InsertAt(0, overflow);
+                                        }
                                     }
                                 }
 
@@ -1249,6 +1253,21 @@ VerticalOrientationType.Rotate or
         // Add the final line.
         if (textLine.Count > 0)
         {
+            if (shouldWrap && (breakWord || breakAll))
+            {
+                while (textLine.ScaledLineAdvance > wrappingLength)
+                {
+                    TextLine overflow = textLine.SplitAt(wrappingLength);
+                    if (overflow == textLine)
+                    {
+                        break;
+                    }
+
+                    textLines.Add(textLine.Finalize(options));
+                    textLine = overflow;
+                }
+            }
+
             textLines.Add(textLine.Finalize(options));
         }
 
@@ -1342,29 +1361,40 @@ public TextLine SplitAt(int index)
                 return this;
             }
 
-            TextLine result = new();
-            result.data.AddRange(this.data.GetRange(index, this.data.Count - index));
+            int count = this.data.Count - index;
+            TextLine result = new(count);
+            result.data.AddRange(this.data.GetRange(index, count));
             RecalculateLineMetrics(result);
 
-            this.data.RemoveRange(index, this.data.Count - index);
+            this.data.RemoveRange(index, count);
             RecalculateLineMetrics(this);
             return result;
         }
 
         public TextLine SplitAt(float length)
         {
-            TextLine result = new();
-            float advance = 0;
-            for (int i = 0; i < this.data.Count; i++)
+            float advance = this.data[0].ScaledAdvance;
+
+            // Ensure at least one glyph is in the line.
+            // trailing whitespace should be ignored as it is trimmed
+            // on finalization.
+            for (int i = 1; i < this.data.Count; i++)
             {
                 GlyphLayoutData glyph = this.data[i];
                 advance += glyph.ScaledAdvance;
+                if (CodePoint.IsWhiteSpace(glyph.CodePoint))
+                {
+                    continue;
+                }
+
                 if (advance >= length)
                 {
-                    result.data.AddRange(this.data.GetRange(i, this.data.Count - i));
+                    int count = this.data.Count - i;
+                    TextLine result = new(count);
+                    result.data.AddRange(this.data.GetRange(i, count));
                     RecalculateLineMetrics(result);
 
-                    this.data.RemoveRange(i, this.data.Count - i);
+                    this.data.RemoveRange(i, count);
                     RecalculateLineMetrics(this);
                     return result;
                 }
diff --git a/tests/Images/ReferenceOutput/BreakWordEnsuresSingleCharacterPerLine__WrappingLength_1_.png b/tests/Images/ReferenceOutput/BreakWordEnsuresSingleCharacterPerLine__WrappingLength_1_.png
new file mode 100644
index 00000000..4cc9c33e
--- /dev/null
+++ b/tests/Images/ReferenceOutput/BreakWordEnsuresSingleCharacterPerLine__WrappingLength_1_.png
@@ -0,0 +1,3 @@
+version https://git-lfs.github.com/spec/v1
+oid sha256:a55c654f4e0748d3fb1f47d1cec8d243774d38257a8dd5db407a2a2a96a33e69
+size 1277
diff --git a/tests/Images/ReferenceOutput/MeasureTextWordBreakMatchesMDN_238-_layoutMode_HorizontalBottomTop-wordBreaking_BreakWord_.png b/tests/Images/ReferenceOutput/MeasureTextWordBreakMatchesMDN_238-_layoutMode_HorizontalBottomTop-wordBreaking_BreakWord_.png
index d0834260..22aa8d7c 100644
--- a/tests/Images/ReferenceOutput/MeasureTextWordBreakMatchesMDN_238-_layoutMode_HorizontalBottomTop-wordBreaking_BreakWord_.png
+++ b/tests/Images/ReferenceOutput/MeasureTextWordBreakMatchesMDN_238-_layoutMode_HorizontalBottomTop-wordBreaking_BreakWord_.png
@@ -1,3 +1,3 @@
 version https://git-lfs.github.com/spec/v1
-oid sha256:5a5ec93c6ece40f6c3577970cd0fa1f97d74d019ed52cf3ce9812b4d805624b0
-size 13613
+oid sha256:65da62dd5894e1bdda14fd9d469205c0cdfecb679617660a48c4ea4b4e5faa1b
+size 13587
diff --git a/tests/Images/ReferenceOutput/MeasureTextWordBreakMatchesMDN_238-_layoutMode_HorizontalTopBottom-wordBreaking_BreakWord_.png b/tests/Images/ReferenceOutput/MeasureTextWordBreakMatchesMDN_238-_layoutMode_HorizontalTopBottom-wordBreaking_BreakWord_.png
index bc6d223a..2ad66506 100644
--- a/tests/Images/ReferenceOutput/MeasureTextWordBreakMatchesMDN_238-_layoutMode_HorizontalTopBottom-wordBreaking_BreakWord_.png
+++ b/tests/Images/ReferenceOutput/MeasureTextWordBreakMatchesMDN_238-_layoutMode_HorizontalTopBottom-wordBreaking_BreakWord_.png
@@ -1,3 +1,3 @@
 version https://git-lfs.github.com/spec/v1
-oid sha256:0d714d870453515f516af0fe8267795df3b36059a9c8c91b0946889985cd089e
-size 13705
+oid sha256:6fe3ad7e51ad713b36ab89c186c1e32c14467ba3320b31f3ce99bf7d4e603050
+size 13669
diff --git a/tests/SixLabors.Fonts.Tests/TextLayoutTests.cs b/tests/SixLabors.Fonts.Tests/TextLayoutTests.cs
index 340aef0a..4e4d9cff 100644
--- a/tests/SixLabors.Fonts.Tests/TextLayoutTests.cs
+++ b/tests/SixLabors.Fonts.Tests/TextLayoutTests.cs
@@ -1206,6 +1206,23 @@ public void IsMeasureCharacterBoundsSameAsRenderBounds()
         }
     }
 
+    [Fact]
+    public void BreakWordEnsuresSingleCharacterPerLine()
+    {
+        Font font = CreateRenderingFont(20);
+        TextOptions options = new(font)
+        {
+            WordBreaking = WordBreaking.BreakWord,
+            WrappingLength = 1
+        };
+
+        const string text = "Hello World!";
+        int lineCount = TextMeasurer.CountLines(text, options);
+        Assert.Equal(text.Length - 1, lineCount);
+
+        TextLayoutTestUtilities.TestLayout(text, options);
+    }
+
     private class CaptureGlyphBoundBuilder : IGlyphRenderer
     {
         public static List<FontRectangle> GenerateGlyphsBoxes(string text, TextOptions options)