diff --git a/fop-core/src/main/java/org/apache/fop/render/pdf/PDFPainter.java b/fop-core/src/main/java/org/apache/fop/render/pdf/PDFPainter.java
index 3ac5505fc66..34cb12adb22 100644
--- a/fop-core/src/main/java/org/apache/fop/render/pdf/PDFPainter.java
+++ b/fop-core/src/main/java/org/apache/fop/render/pdf/PDFPainter.java
@@ -607,15 +607,22 @@ private void drawTextWithDX(int x, int y, String text, FontTriplet triplet,
         endSimulateStyle(tf, triplet);
     }
 
+    /**
+     * Synthesises the style a triplet names from the face it is registered on, where the font entry asks for it
+     * (simulate-style), as Word synthesises a style a family lacks: a bold triplet is stroked at 1/35 em, and an
+     * italic one sheared by 0.3333, each only where the face is not bold, or not italic, already.
+     * @return the shear for the text matrix
+     */
     private double startSimulateStyle(Typeface tf, FontTriplet triplet) {
         double shear = 0;
         boolean simulateStyle = tf instanceof CustomFont && ((CustomFont) tf).getSimulateStyle();
         if (simulateStyle) {
-            if (triplet.getWeight() == 700) {
+            CustomFont face = (CustomFont) tf;
+            if (simulatesBold(face, triplet)) {
                 generator.updateColor(state.getTextColor(), false, null);
-                generator.add("2 Tr 0.31543 w\n");
+                generator.add("2 Tr " + PDFNumber.doubleOut(state.getFontSize() / 1000.0 / 35, 5) + " w\n");
             }
-            if (triplet.getStyle().equals("italic")) {
+            if (triplet.getStyle().equals("italic") && face.getItalicAngle() == 0) {
                 shear = 0.3333;
             }
         }
@@ -624,11 +631,16 @@ private double startSimulateStyle(Typeface tf, FontTriplet triplet) {
 
     private void endSimulateStyle(Typeface tf, FontTriplet triplet) {
         boolean simulateStyle = tf instanceof CustomFont && ((CustomFont) tf).getSimulateStyle();
-        if (simulateStyle && triplet.getWeight() == 700) {
+        if (simulateStyle && simulatesBold((CustomFont) tf, triplet)) {
             generator.add("0 Tr\n");
         }
     }
 
+    /** A bold triplet on a face that is not bold already (its weight class below 700, or unknown). */
+    private static boolean simulatesBold(CustomFont face, FontTriplet triplet) {
+        return triplet.getWeight() == 700 && face.getWeight() < 700;
+    }
+
     private static int[] paZero = new int[4];
 
     private void drawTextWithDP(int x, int y, String text, FontTriplet triplet,
diff --git a/fop-core/src/test/java/org/apache/fop/render/pdf/PDFPainterTestCase.java b/fop-core/src/test/java/org/apache/fop/render/pdf/PDFPainterTestCase.java
index bd6cf5b2488..a4afd430772 100644
--- a/fop-core/src/test/java/org/apache/fop/render/pdf/PDFPainterTestCase.java
+++ b/fop-core/src/test/java/org/apache/fop/render/pdf/PDFPainterTestCase.java
@@ -44,6 +44,7 @@
 import static org.junit.Assert.assertEquals;
 import static org.junit.Assert.assertTrue;
 import static org.mockito.ArgumentMatchers.any;
+import static org.mockito.ArgumentMatchers.contains;
 import static org.mockito.ArgumentMatchers.endsWith;
 import static org.mockito.ArgumentMatchers.eq;
 import static org.mockito.ArgumentMatchers.nullable;
@@ -290,14 +291,67 @@ public void testSimulateStyle() throws IFException {
         fi.addMetrics("f1", font);
         pdfDocumentHandler.setFontInfo(fi);
         MyPDFPainter pdfPainter = new MyPDFPainter(pdfDocumentHandler, null);
-        pdfPainter.setFont("a", "italic", 700, null, 12, null);
+        pdfPainter.setFont("a", "italic", 700, null, 11040, null);
+        pdfPainter.drawText(0, 0, 0, 0, null, "test");
+
+        assertEquals(sb.toString(), "BT\n/f1 11.04 Tf\n1 0 0.3333 -1 0 0 Tm [<0000000000000000>] TJ\n");
+        verify(pdfContentGenerator).add("2 Tr 0.31543 w\n");
+        verify(pdfContentGenerator).add("0 Tr\n");
+    }
+
+    /** The output of a bold italic triplet on a face, at a size, for the simulated-style tests. */
+    private String simulateStyle(MultiByteFont font, int size) throws IFException {
+        final StringBuilder sb = new StringBuilder();
+        pdfDocumentHandler = makePDFDocumentHandler(sb);
+        FontInfo fi = new FontInfo();
+        fi.addFontProperties("f1", new FontTriplet("a", "italic", 700));
+        font.setSimulateStyle(true);
+        fi.addMetrics("f1", font);
+        pdfDocumentHandler.setFontInfo(fi);
+        MyPDFPainter pdfPainter = new MyPDFPainter(pdfDocumentHandler, null);
+        pdfPainter.setFont("a", "italic", 700, null, size, null);
         pdfPainter.drawText(0, 0, 0, 0, null, "test");
+        return sb.toString();
+    }
 
-        assertEquals(sb.toString(), "BT\n/f1 0.012 Tf\n1 0 0.3333 -1 0 0 Tm [<0000000000000000>] TJ\n");
+    /**
+     * An italic face is not slanted again, but is stroked, as Word draws the italic face of a family that has no
+     * bold one.
+     * @throws IFException if the painting fails
+     */
+    @Test
+    public void testSimulateStyleItalicFaceIsNotSheared() throws IFException {
+        MultiByteFont font = new MultiByteFont(null, null);
+        font.setItalicAngle(-11);
+        assertEquals("BT\n/f1 11.04 Tf\n1 0 0 -1 0 0 Tm [<0000000000000000>] TJ\n", simulateStyle(font, 11040));
         verify(pdfContentGenerator).add("2 Tr 0.31543 w\n");
         verify(pdfContentGenerator).add("0 Tr\n");
     }
 
+    /**
+     * A bold face is not stroked again, but is sheared, as Word draws the bold face of a family that has no bold
+     * italic one.
+     * @throws IFException if the painting fails
+     */
+    @Test
+    public void testSimulateStyleBoldFaceIsNotStroked() throws IFException {
+        MultiByteFont font = new MultiByteFont(null, null);
+        font.setWeight(700);
+        assertEquals("BT\n/f1 11.04 Tf\n1 0 0.3333 -1 0 0 Tm [<0000000000000000>] TJ\n", simulateStyle(font, 11040));
+        verify(pdfContentGenerator, never()).add(contains(" Tr "));
+        verify(pdfContentGenerator, never()).add("0 Tr\n");
+    }
+
+    /**
+     * The simulated bold's stroke is 1/35 em, Word's at every size: 0.63086 at 22.08pt.
+     * @throws IFException if the painting fails
+     */
+    @Test
+    public void testSimulateStyleStrokeScalesWithSize() throws IFException {
+        simulateStyle(new MultiByteFont(null, null), 22080);
+        verify(pdfContentGenerator).add("2 Tr 0.63086 w\n");
+    }
+
     @Test
     public void testSoftHyphenNotReplaced() throws IFException {
         pdfDocumentHandler = makePDFDocumentHandler(new StringBuilder());
@@ -376,7 +430,7 @@ public void testSimulateStyleColor() throws Exception {
         fi.addMetrics("f1", font);
         pdfDocumentHandler.setFontInfo(fi);
         PDFPainter pdfPainter = new PDFPainter(pdfDocumentHandler, null);
-        pdfPainter.setFont("a", "italic", 700, null, 12, Color.red);
+        pdfPainter.setFont("a", "italic", 700, null, 11040, Color.red);
         pdfPainter.drawText(0, 0, 0, 0, null, "test");
 
         ByteArrayOutputStream bos = new ByteArrayOutputStream();
@@ -389,7 +443,7 @@ public void testSimulateStyleColor() throws Exception {
                 + "1 0 0 -1 0 0 cm\n"
                 + "1 0 0 rg\n"
                 + "BT\n"
-                + "/f1 0.012 Tf\n"
+                + "/f1 11.04 Tf\n"
                 + "1 0 0 RG\n"
                 + "2 Tr 0.31543 w\n"
                 + "1 0 0.3333 -1 0 0 Tm [<0000000000000000>] TJ\n"