diff --git a/src/SixLabors.Fonts/FontGlyphMetrics.cs b/src/SixLabors.Fonts/FontGlyphMetrics.cs
index 96978973..74883360 100644
--- a/src/SixLabors.Fonts/FontGlyphMetrics.cs
+++ b/src/SixLabors.Fonts/FontGlyphMetrics.cs
@@ -16,6 +16,13 @@ public abstract class FontGlyphMetrics
 {
     private static readonly Vector2 YInverter = new(1, -1);
 
+    /// <summary>
+    /// The horizontal shear applied to synthesize an oblique (faux italic) slant when an italic
+    /// style is requested but the resolved font face provides no italic face. This equals the
+    /// tangent of a 14 degree slant, matching the default oblique angle used by web browsers.
+    /// </summary>
+    private const float SyntheticObliqueSkew = 0.24932839F;
+
     internal FontGlyphMetrics(
         StreamFontMetrics font,
         ushort glyphId,
@@ -240,6 +247,42 @@ internal void ApplyAdvance(short x, short y)
     /// <param name="y">The y-advance.</param>
     internal void SetAdvanceHeight(ushort y) => this.AdvanceHeight = y;
 
+    /// <summary>
+    /// Gets the horizontal shear factor used to synthesize an oblique (faux italic) slant for
+    /// this glyph. A non-zero value is returned only when the associated text run requests an
+    /// italic style that the resolved font face does not itself provide, mirroring the CSS
+    /// <c>font-synthesis: style</c> behavior used by web browsers.
+    /// </summary>
+    /// <returns>
+    /// The shear factor to apply in the glyph's Y-up coordinate space, or <c>0</c> when no
+    /// synthesis is required.
+    /// </returns>
+    internal float GetObliqueSkew()
+    {
+        Font? font = this.TextRun?.Font;
+        if (font is null)
+        {
+            return 0F;
+        }
+
+        bool requestedItalic = (font.RequestedStyle & FontStyle.Italic) == FontStyle.Italic;
+        bool resolvedItalic = (this.FontMetrics.Description.Style & FontStyle.Italic) == FontStyle.Italic;
+        return requestedItalic && !resolvedItalic ? SyntheticObliqueSkew : 0F;
+    }
+
+    /// <summary>
+    /// Creates a horizontal shear matrix for the given oblique skew factor, expressed in the
+    /// glyph's Y-up coordinate space.
+    /// </summary>
+    /// <param name="skew">The horizontal shear factor.</param>
+    /// <returns>The shear <see cref="Matrix3x2"/>.</returns>
+    internal static Matrix3x2 CreateObliqueMatrix(float skew)
+    {
+        Matrix3x2 matrix = Matrix3x2.Identity;
+        matrix.M21 = skew;
+        return matrix;
+    }
+
     /// <summary>
     /// Calculates the glyph bounding box in device-space (Y-down) coordinates,
     /// given the layout mode, render origin, and scaled point size.
@@ -279,6 +322,17 @@ internal FontRectangle GetBoundingBox(GlyphLayoutMode mode, Vector2 origin, floa
 
         // 2) Rotate for vertical rotated layout.
         Vector2 offsetUp = this.Offset;
+
+        // Apply synthetic oblique (faux italic) shear before rotation so that the reported ink
+        // bounds match the sheared outline produced during rendering.
+        float skew = this.GetObliqueSkew();
+        if (skew != 0F)
+        {
+            Matrix3x2 oblique = CreateObliqueMatrix(skew);
+            b = Bounds.Transform(in b, oblique);
+            offsetUp = Vector2.Transform(offsetUp, oblique);
+        }
+
         if (mode == GlyphLayoutMode.VerticalRotated)
         {
             Matrix3x2 rot = Matrix3x2.CreateRotation(-MathF.PI / 2F);
diff --git a/src/SixLabors.Fonts/Tables/Cff/CffGlyphMetrics.cs b/src/SixLabors.Fonts/Tables/Cff/CffGlyphMetrics.cs
index 2b7e6898..57e967f2 100644
--- a/src/SixLabors.Fonts/Tables/Cff/CffGlyphMetrics.cs
+++ b/src/SixLabors.Fonts/Tables/Cff/CffGlyphMetrics.cs
@@ -148,6 +148,12 @@ internal override void RenderTo(
         float scaledPPEM = this.GetScaledSize(pointSize, dpi);
 
         Matrix3x2 rotation = GetRotationMatrix(mode);
+
+        // Synthesize an oblique (faux italic) slant when requested but unavailable by shearing
+        // the outline in the glyph's Y-up space before rotation is applied.
+        float skew = this.GetObliqueSkew();
+        Matrix3x2 transform = skew != 0F ? CreateObliqueMatrix(skew) * rotation : rotation;
+
         FontRectangle box = this.GetBoundingBox(mode, glyphOrigin, scaledPPEM);
         GlyphRendererParameters parameters = new(this, this.TextRun, pointSize, dpi, mode, graphemeIndex);
 
@@ -167,7 +173,7 @@ internal override void RenderTo(
                 }
 
                 Vector2 scaledOffset = this.Offset * scale;
-                this.glyphData.RenderTo(renderer, glyphOrigin, scale, scaledOffset, rotation);
+                this.glyphData.RenderTo(renderer, glyphOrigin, scale, scaledOffset, transform);
             }
 
             renderer.EndGlyph();
diff --git a/src/SixLabors.Fonts/Tables/TrueType/TrueTypeGlyphMetrics.cs b/src/SixLabors.Fonts/Tables/TrueType/TrueTypeGlyphMetrics.cs
index 257779c3..27d08ef2 100644
--- a/src/SixLabors.Fonts/Tables/TrueType/TrueTypeGlyphMetrics.cs
+++ b/src/SixLabors.Fonts/Tables/TrueType/TrueTypeGlyphMetrics.cs
@@ -175,6 +175,14 @@ internal override void RenderTo(
                     float pixelSize = scaledPPEM / 72F;
                     this.FontMetrics.ApplyTrueTypeHinting(this.GetHintingMode(options.HintingMode), this, ref clone, scale, pixelSize);
 
+                    // Synthesize an oblique (faux italic) slant when requested but unavailable.
+                    // Applied after hinting so the hinter operates on the upright outline.
+                    float skew = this.GetObliqueSkew();
+                    if (skew != 0F)
+                    {
+                        GlyphVector.TransformInPlace(ref clone, CreateObliqueMatrix(skew));
+                    }
+
                     // Rotation must happen after hinting.
                     GlyphVector.TransformInPlace(ref clone, rotation);
                     return clone;
diff --git a/tests/SixLabors.Fonts.Tests/FontSynthesisTests.cs b/tests/SixLabors.Fonts.Tests/FontSynthesisTests.cs
new file mode 100644
index 00000000..5bd6720f
--- /dev/null
+++ b/tests/SixLabors.Fonts.Tests/FontSynthesisTests.cs
@@ -0,0 +1,137 @@
+// Copyright (c) Six Labors.
+// Licensed under the Six Labors Split License.
+
+using System.Numerics;
+using SixLabors.Fonts.Rendering;
+using SixLabors.Fonts.Unicode;
+
+namespace SixLabors.Fonts.Tests;
+
+public class FontSynthesisTests
+{
+    // tan(14 degrees) - the default oblique slant browsers apply for synthesized italics.
+    private static readonly float ExpectedSkew = MathF.Tan(14F * MathF.PI / 180F);
+
+    private static readonly ApproximateFloatComparer SkewComparer = new(0.001F);
+
+    private static readonly ApproximateFloatComparer GeometryComparer = new(0.1F);
+
+    private static FontFamily RegularOnlyFamily(string file)
+        => new FontCollection().Add(file);
+
+    [Fact]
+    public void FamilyWithoutItalic_FallsBackToRegularMetrics()
+    {
+        FontFamily family = RegularOnlyFamily(TestFonts.OpenSansFile);
+        Font italic = new(family, 24, FontStyle.Italic);
+
+        // Italic was requested but the resolved face is still the regular one.
+        Assert.Equal(FontStyle.Italic, italic.RequestedStyle);
+        Assert.False(italic.IsItalic);
+    }
+
+    [Fact]
+    public void GetObliqueSkew_TrueType_NonZeroOnlyWhenItalicSynthesized()
+        => AssertObliqueSkew(TestFonts.OpenSansFile);
+
+    [Fact]
+    public void GetObliqueSkew_Cff_NonZeroOnlyWhenItalicSynthesized()
+        => AssertObliqueSkew(TestFonts.PlantinStdRegularFile);
+
+    [Fact]
+    public void SyntheticItalic_ShearsGlyphOutline_TrueType()
+        => AssertSyntheticItalicShear(TestFonts.OpenSansFile, "Hg");
+
+    [Fact]
+    public void SyntheticItalic_ShearsGlyphOutline_Cff()
+        => AssertSyntheticItalicShear(TestFonts.PlantinStdRegularFile, "Hg");
+
+    [Fact]
+    public void SyntheticItalic_DoesNotChangeAdvance_ButWidensBounds()
+    {
+        FontFamily family = RegularOnlyFamily(TestFonts.OpenSansFile);
+        Font regular = new(family, 48, FontStyle.Regular);
+        Font italic = new(family, 48, FontStyle.Italic);
+
+        const string text = "Hg";
+
+        // The advance width is a layout metric and must be unchanged by synthesis so that
+        // spacing continues to match a browser rendering the same regular face.
+        FontRectangle regularAdvance = TextMeasurer.MeasureAdvance(text, new TextOptions(regular));
+        FontRectangle italicAdvance = TextMeasurer.MeasureAdvance(text, new TextOptions(italic));
+        Assert.Equal(regularAdvance.Width, italicAdvance.Width, SkewComparer);
+
+        // The rendered ink bounds however widen because the outline is sheared.
+        FontRectangle regularBounds = TextMeasurer.MeasureBounds(text, new TextOptions(regular));
+        FontRectangle italicBounds = TextMeasurer.MeasureBounds(text, new TextOptions(italic));
+        Assert.True(italicBounds.Width > regularBounds.Width);
+    }
+
+    [Fact]
+    public void GetObliqueSkew_ReturnsZero_WhenGlyphHasNoTextRun()
+    {
+        // The metrics returned directly from the font (i.e. not cloned for a specific run)
+        // carry no text run, so synthesis cannot be determined and must be disabled.
+        Font italic = new(RegularOnlyFamily(TestFonts.OpenSansFile), 24, FontStyle.Italic);
+
+        Assert.True(italic.FontMetrics.TryGetGlyphMetrics(
+            new CodePoint('H'),
+            TextAttributes.None,
+            TextDecorations.None,
+            LayoutMode.HorizontalTopBottom,
+            ColorFontSupport.None,
+            out FontGlyphMetrics metrics));
+
+        Assert.Equal(0F, metrics.GetObliqueSkew());
+    }
+
+    private static void AssertObliqueSkew(string file)
+    {
+        FontFamily family = RegularOnlyFamily(file);
+        CodePoint codePoint = new('H');
+
+        Font regular = new(family, 24, FontStyle.Regular);
+        Font italic = new(family, 24, FontStyle.Italic);
+
+        Assert.True(regular.TryGetGlyphs(codePoint, out Glyph? regularGlyph));
+        Assert.True(italic.TryGetGlyphs(codePoint, out Glyph? italicGlyph));
+
+        Assert.Equal(0F, regularGlyph.Value.GlyphMetrics.GetObliqueSkew());
+        Assert.Equal(ExpectedSkew, italicGlyph.Value.GlyphMetrics.GetObliqueSkew(), SkewComparer);
+    }
+
+    private static void AssertSyntheticItalicShear(string file, string text)
+    {
+        FontFamily family = RegularOnlyFamily(file);
+        Font regular = new(family, 48, FontStyle.Regular);
+        Font italic = new(family, 48, FontStyle.Italic);
+
+        GlyphRenderer regularRenderer = new();
+        TextRenderer.RenderTextTo(regularRenderer, text, new TextOptions(regular) { HintingMode = HintingMode.None });
+
+        GlyphRenderer italicRenderer = new();
+        TextRenderer.RenderTextTo(italicRenderer, text, new TextOptions(italic) { HintingMode = HintingMode.None });
+
+        List<Vector2> r = regularRenderer.ControlPoints;
+        List<Vector2> i = italicRenderer.ControlPoints;
+
+        Assert.NotEmpty(r);
+        Assert.Equal(r.Count, i.Count);
+
+        // The synthesized slant is a pure horizontal shear applied in the glyph's Y-up space.
+        // In device space (Y-down) this means the Y coordinate of every point is preserved and
+        // the horizontal displacement satisfies xi - xr = skew * (originY - yr), so the quantity
+        // (xi - xr) + skew * yr is constant across every emitted control point.
+        float invariant = (i[0].X - r[0].X) + (ExpectedSkew * r[0].Y);
+        float maxHorizontalShift = 0F;
+        for (int p = 0; p < r.Count; p++)
+        {
+            Assert.Equal(r[p].Y, i[p].Y, GeometryComparer);
+            Assert.Equal(invariant, (i[p].X - r[p].X) + (ExpectedSkew * r[p].Y), GeometryComparer);
+            maxHorizontalShift = MathF.Max(maxHorizontalShift, MathF.Abs(i[p].X - r[p].X));
+        }
+
+        // Ensure the glyph was actually slanted and not left upright.
+        Assert.True(maxHorizontalShift > 1F);
+    }
+}