diff --git a/vcl/qa/cppunit/pdfexport/data/drop_fly_paint.fodt b/vcl/qa/cppunit/pdfexport/data/drop_fly_paint.fodt
new file mode 100644
index 000000000000..3ed20104b1f0
--- /dev/null
+++ b/vcl/qa/cppunit/pdfexport/data/drop_fly_paint.fodt
@@ -0,0 +1,50 @@
+<?xml version="1.0" encoding="UTF-8"?>
+<office:document xmlns:office="urn:oasis:names:tc:opendocument:xmlns:office:1.0"
+    xmlns:style="urn:oasis:names:tc:opendocument:xmlns:style:1.0"
+    xmlns:text="urn:oasis:names:tc:opendocument:xmlns:text:1.0"
+    xmlns:fo="urn:oasis:names:tc:opendocument:xmlns:xsl-fo-compatible:1.0"
+    xmlns:draw="urn:oasis:names:tc:opendocument:xmlns:drawing:1.0"
+    xmlns:svg="urn:oasis:names:tc:opendocument:xmlns:svg-compatible:1.0"
+    office:mimetype="application/vnd.oasis.opendocument.text">
+ <office:font-face-decls>
+  <style:font-face style:name="Liberation Sans" svg:font-family="Liberation Sans"
+      style:font-family-generic="swiss" style:font-pitch="variable"/>
+ </office:font-face-decls>
+ <office:automatic-styles>
+  <style:style style:name="PageLayout" style:family="page-layout">
+   <style:page-layout-properties fo:page-width="10cm" fo:page-height="15cm"
+       fo:margin-top="1cm" fo:margin-bottom="1cm" fo:margin-left="1cm" fo:margin-right="1cm"/>
+  </style:style>
+  <style:style style:name="DropCapStyle" style:family="paragraph">
+   <style:text-properties style:font-name="Liberation Sans"
+       style:font-name-asian="Liberation Sans"
+       style:font-name-complex="Liberation Sans"
+       fo:font-size="12pt"
+       style:font-size-asian="12pt"
+       style:font-size-complex="12pt"/>
+   <style:paragraph-properties>
+    <style:drop-cap style:lines="3" style:length="1"/>
+   </style:paragraph-properties>
+  </style:style>
+  <style:style style:name="FlyParaStyle" style:family="paragraph">
+   <style:text-properties style:font-name="Liberation Sans"
+       style:font-name-asian="Liberation Sans"
+       style:font-name-complex="Liberation Sans"
+       fo:font-size="12pt"
+       style:font-size-asian="12pt"
+       style:font-size-complex="12pt"/>
+  </style:style>
+  <style:style style:name="FlyWrap" style:family="graphic">
+   <style:graphic-properties style:wrap="parallel"/>
+  </style:style>
+ </office:automatic-styles>
+ <office:master-styles>
+  <style:master-page style:name="Standard" style:page-layout-name="PageLayout"/>
+ </office:master-styles>
+ <office:body>
+  <office:text>
+   <text:p text:style-name="DropCapStyle">Drop Cap Painting Test Document.<text:line-break/>Second forced line of the drop cap paragraph.<text:line-break/>Third forced line of the drop cap paragraph.</text:p>
+   <text:p text:style-name="FlyParaStyle"><draw:rect draw:style-name="FlyWrap" text:anchor-type="paragraph" svg:width="2cm" svg:height="1.5cm" svg:x="0cm" svg:y="0cm"/>Fly frame paragraph line one.<text:line-break/>Fly frame paragraph line two.<text:line-break/>Fly frame paragraph line three.</text:p>
+  </office:text>
+ </office:body>
+</office:document>
diff --git a/vcl/qa/cppunit/pdfexport/pdfexport2.cxx b/vcl/qa/cppunit/pdfexport/pdfexport2.cxx
index 23a1b8afd51f..26fef6a45141 100644
--- a/vcl/qa/cppunit/pdfexport/pdfexport2.cxx
+++ b/vcl/qa/cppunit/pdfexport/pdfexport2.cxx
@@ -6928,6 +6928,50 @@ CPPUNIT_TEST_FIXTURE(PdfExportTest2, testTdf117941RtlStrikeoutChars)
     CPPUNIT_ASSERT_DOUBLES_EQUAL(565.2, aRect.at(7).getMaxX(), /*delta*/ 1.0);
 }
 
+CPPUNIT_TEST_FIXTURE(PdfExportTest2, testDropCapPaint)
+{
+    loadFromFile(u"drop_fly_paint.fodt");
+    save(TestFilter::PDF_WRITER);
+
+    std::vector<OUString> aText;
+    std::vector<basegfx::B2DRectangle> aRect;
+    GetPdfPageTextObjectsAndBounds(parsePDFExport(), /*nPage*/ 0, aText, aRect);
+
+    CPPUNIT_ASSERT_EQUAL(size_t(7), aText.size());
+
+    // Rest of the drop-capped paragraph's 3 forced lines.
+    CPPUNIT_ASSERT_EQUAL(u"rop Cap Painting Test Document."_ustr, aText.at(0).trim());
+    CPPUNIT_ASSERT_EQUAL(u"Second forced line of the drop cap paragraph."_ustr, aText.at(1).trim());
+    CPPUNIT_ASSERT_EQUAL(u"Third forced line of the drop cap paragraph."_ustr, aText.at(2).trim());
+
+    // The drop cap glyph itself must be non-whitespace.
+    CPPUNIT_ASSERT_EQUAL(u"D"_ustr, aText.at(3).trim());
+
+    // Must be noticeably taller than a body line (spans 3 lines), not
+    // just present-but-same-height.
+    double nDropCapHeight = aRect.at(3).getMaxY() - aRect.at(3).getMinY();
+    double nBodyLineHeight = aRect.at(2).getMaxY() - aRect.at(2).getMinY();
+    CPPUNIT_ASSERT(nDropCapHeight > nBodyLineHeight * 2.5);
+
+    // Sits left of the wrapped text beside it, not overlapping/underneath.
+    CPPUNIT_ASSERT(aRect.at(3).getMaxX() < aRect.at(0).getMinX());
+
+    CPPUNIT_ASSERT_DOUBLES_EQUAL(61.33, aRect.at(3).getMinX(), /*delta*/ 2.0);
+    CPPUNIT_ASSERT_DOUBLES_EQUAL(94.00, aRect.at(3).getMaxX(), /*delta*/ 2.0);
+    CPPUNIT_ASSERT_DOUBLES_EQUAL(696.45, aRect.at(3).getMinY(), /*delta*/ 2.0);
+    CPPUNIT_ASSERT_DOUBLES_EQUAL(734.43, aRect.at(3).getMaxY(), /*delta*/ 2.0);
+
+    // Second paragraph: text wrapping around the anchored fly frame.
+    CPPUNIT_ASSERT_EQUAL(u"Fly frame paragraph line one."_ustr, aText.at(4).trim());
+    CPPUNIT_ASSERT_EQUAL(u"Fly frame paragraph line two."_ustr, aText.at(5).trim());
+    CPPUNIT_ASSERT_EQUAL(u"Fly frame paragraph line three."_ustr, aText.at(6).trim());
+
+    // Every line starts well to the right of the drop-cap paragraph's own
+    // margin, confirming wrap="parallel" is actually pushing text aside.
+    CPPUNIT_ASSERT(aRect.at(4).getMinX() > aRect.at(0).getMinX() + 10.0);
+    CPPUNIT_ASSERT_DOUBLES_EQUAL(114.53, aRect.at(4).getMinX(), /*delta*/ 2.0);
+}
+
 } // end anonymous namespace
 
 CPPUNIT_PLUGIN_IMPLEMENT();