@@ -36,3 +36,33 @@ def test_clip():
         assert bbox.intersects(
             rect
         ), f"Character '{char['c']}' at {bbox} is outside of {rect}."
+
+
+def test_5108():
+    print()
+    path = os.path.normpath(f'{__file__}/../../tests/resources/test_5108.pdf')
+    def clipped_content(i, clip):
+        with pymupdf.open(path) as document:
+            page = document[0]
+            page.clip_to_rect(clip)
+            with pymupdf.open(stream=document.tobytes(garbage=3, clean=True)) as document2:
+                page = document2[0]
+                ret = b''.join(document2.xref_stream(x) for x in page.get_contents())
+                page.draw_rect(clip, (1, 0, 0))
+                document2.save(f'{path}.out.{i}.pdf')
+                return ret
+    for i, (label, clip) in enumerate([
+            ('whole page                            ', pymupdf.Rect(0, 0, 400, 400)),
+            ('right half (holds shading)            ', pymupdf.Rect(200, 0, 400, 400)),
+            ('page inset by 1pt                     ', pymupdf.Rect(1, 1, 399, 399)),
+            ('1x1 at PDF origin, no shading in it   ', pymupdf.Rect(0, 399, 1, 400)),
+            ('                                      ', pymupdf.Rect(0, 0, 10, 10)),
+            ('                                      ', pymupdf.Rect(0, 2, 10, 7)),
+            ]):
+        content = clipped_content(i, clip)
+        sh_kept = str(b'sh' in content)
+        print(f'    {label} -> {sh_kept=:5s} {content!r}')    
+
+
+        
+