diff --git a/Tests/helper.py b/Tests/helper.py
index 59ba0dd15..707926b98 100644
--- a/Tests/helper.py
+++ b/Tests/helper.py
@@ -173,6 +173,16 @@ def skip_unless_feature_version(feature, version_required, reason=None):
     return pytest.mark.skipif(version_available < version_required, reason=reason)
 
 
+def mark_if_feature_version(mark, feature, version_blacklist, reason=None):
+    if not features.check(feature):
+        return
+    if reason is None:
+        reason = f"{feature} is {version_blacklist}"
+    version_required = parse_version(version_blacklist)
+    version_available = parse_version(features.version(feature))
+    return mark(version_available == version_blacklist, reason=reason)
+
+
 @pytest.mark.skipif(sys.platform.startswith("win32"), reason="Requires Unix or macOS")
 class PillowLeakTestCase:
     # requires unix/macOS
diff --git a/Tests/test_file_eps.py b/Tests/test_file_eps.py
index 7caac34c3..5007af6ef 100644
--- a/Tests/test_file_eps.py
+++ b/Tests/test_file_eps.py
@@ -9,6 +9,7 @@ from .helper import (
     assert_image_similar_tofile,
     hopper,
     skip_unless_feature,
+    mark_if_feature_version,
 )
 
 HAS_GHOSTSCRIPT = EpsImagePlugin.has_ghostscript()
@@ -64,7 +65,7 @@ def test_invalid_file():
         EpsImagePlugin.EpsImageFile(invalid_file)
 
 
-@pytest.mark.valgrind_known_error(reason="Known Failing")
+@mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
 @pytest.mark.skipif(not HAS_GHOSTSCRIPT, reason="Ghostscript not available")
 def test_cmyk():
     with Image.open("Tests/images/pil_sample_cmyk.eps") as cmyk_image:
diff --git a/Tests/test_file_jpeg.py b/Tests/test_file_jpeg.py
index 64f509a95..1c14bd205 100644
--- a/Tests/test_file_jpeg.py
+++ b/Tests/test_file_jpeg.py
@@ -25,6 +25,7 @@ from .helper import (
     hopper,
     is_win32,
     skip_unless_feature,
+    mark_if_feature_version,
 )
 
 TEST_FILE = "Tests/images/hopper.jpg"
@@ -116,7 +117,7 @@ class TestFileJpeg:
         assert test(100, 200) == (100, 200)
         assert test(0) is None  # square pixels
 
-    @pytest.mark.valgrind_known_error(reason="Known Failing")
+    @mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
     def test_icc(self, tmp_path):
         # Test ICC support
         with Image.open("Tests/images/rgb.jpg") as im1:
@@ -156,7 +157,7 @@ class TestFileJpeg:
         test(ImageFile.MAXBLOCK + 1)  # full buffer block plus one byte
         test(ImageFile.MAXBLOCK * 4 + 3)  # large block
 
-    @pytest.mark.valgrind_known_error(reason="Known Failing")
+    @mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
     def test_large_icc_meta(self, tmp_path):
         # https://github.com/python-pillow/Pillow/issues/148
         # Sometimes the meta data on the icc_profile block is bigger than
@@ -423,7 +424,7 @@ class TestFileJpeg:
         with Image.open(filename):
             pass
 
-    @pytest.mark.valgrind_known_error(reason="Known Failing")
+    @mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
     def test_truncated_jpeg_should_read_all_the_data(self):
         filename = "Tests/images/truncated_jpeg.jpg"
         ImageFile.LOAD_TRUNCATED_IMAGES = True
@@ -442,7 +443,7 @@ class TestFileJpeg:
             with pytest.raises(OSError):
                 im.load()
 
-    @pytest.mark.valgrind_known_error(reason="Known Failing")
+    @mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
     def test_qtables(self, tmp_path):
         def _n_qtables_helper(n, test_file):
             with Image.open(test_file) as im:
@@ -726,7 +727,7 @@ class TestFileJpeg:
             # OSError for unidentified image.
             assert im.info.get("dpi") == (72, 72)
 
-    @pytest.mark.valgrind_known_error(reason="Known Failing")
+    @mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
     def test_exif_x_resolution(self, tmp_path):
         with Image.open("Tests/images/flower.jpg") as im:
             exif = im.getexif()
@@ -757,7 +758,7 @@ class TestFileJpeg:
             # Act / Assert
             assert im._getexif()[306] == "2017:03:13 23:03:09"
 
-    @pytest.mark.valgrind_known_error(reason="Backtrace in Python Core")
+    @mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
     def test_photoshop(self):
         with Image.open("Tests/images/photoshop-200dpi.jpg") as im:
             assert im.info["photoshop"][0x03ED] == {
diff --git a/Tests/test_file_libtiff.py b/Tests/test_file_libtiff.py
index 22b641b5f..c1c9df7b1 100644
--- a/Tests/test_file_libtiff.py
+++ b/Tests/test_file_libtiff.py
@@ -18,6 +18,7 @@ from .helper import (
     assert_image_similar_tofile,
     hopper,
     skip_unless_feature,
+    mark_if_feature_version,
 )
 
 
@@ -822,13 +823,13 @@ class TestFileLibTiff(LibTiffTestCase):
         with Image.open(infile) as im:
             assert_image_similar_tofile(im, "Tests/images/pil_sample_cmyk.jpg", 0.5)
 
-    @pytest.mark.valgrind_known_error(reason="Known Failing")
+    @mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
     def test_strip_ycbcr_jpeg_2x2_sampling(self):
         infile = "Tests/images/tiff_strip_ycbcr_jpeg_2x2_sampling.tif"
         with Image.open(infile) as im:
             assert_image_similar_tofile(im, "Tests/images/flower.jpg", 0.5)
 
-    @pytest.mark.valgrind_known_error(reason="Known Failing")
+    @mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
     def test_strip_ycbcr_jpeg_1x1_sampling(self):
         infile = "Tests/images/tiff_strip_ycbcr_jpeg_1x1_sampling.tif"
         with Image.open(infile) as im:
@@ -839,13 +840,13 @@ class TestFileLibTiff(LibTiffTestCase):
         with Image.open(infile) as im:
             assert_image_similar_tofile(im, "Tests/images/pil_sample_cmyk.jpg", 0.5)
 
-    @pytest.mark.valgrind_known_error(reason="Known Failing")
+    @mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
     def test_tiled_ycbcr_jpeg_1x1_sampling(self):
         infile = "Tests/images/tiff_tiled_ycbcr_jpeg_1x1_sampling.tif"
         with Image.open(infile) as im:
             assert_image_equal_tofile(im, "Tests/images/flower2.jpg")
 
-    @pytest.mark.valgrind_known_error(reason="Known Failing")
+    @mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
     def test_tiled_ycbcr_jpeg_2x2_sampling(self):
         infile = "Tests/images/tiff_tiled_ycbcr_jpeg_2x2_sampling.tif"
         with Image.open(infile) as im:
diff --git a/Tests/test_file_pdf.py b/Tests/test_file_pdf.py
index e5bba483a..1a9b4847c 100644
--- a/Tests/test_file_pdf.py
+++ b/Tests/test_file_pdf.py
@@ -8,7 +8,8 @@ import pytest
 
 from PIL import Image, PdfParser
 
-from .helper import hopper
+from .helper import hopper, mark_if_feature_version
+
 
 
 def helper_save_as_pdf(tmp_path, mode, **kwargs):
@@ -85,7 +86,7 @@ def test_unsupported_mode(tmp_path):
         im.save(outfile)
 
 
-@pytest.mark.valgrind_known_error(reason="Known Failing")
+@mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
 def test_save_all(tmp_path):
     # Single frame image
     helper_save_as_pdf(tmp_path, "RGB", save_all=True)
diff --git a/Tests/test_file_png.py b/Tests/test_file_png.py
index bbf5f5772..74bba7ce9 100644
--- a/Tests/test_file_png.py
+++ b/Tests/test_file_png.py
@@ -14,6 +14,7 @@ from .helper import (
     is_big_endian,
     is_win32,
     skip_unless_feature,
+    mark_if_feature_version,
 )
 
 # sample png stream
@@ -679,7 +680,7 @@ class TestFilePng:
             exif = reloaded._getexif()
         assert exif[274] == 1
 
-    @pytest.mark.valgrind_known_error(reason="Known Failing")
+    @mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
     def test_exif_from_jpg(self, tmp_path):
         with Image.open("Tests/images/pil_sample_rgb.jpg") as im:
             test_file = str(tmp_path / "temp.png")
diff --git a/Tests/test_file_webp_metadata.py b/Tests/test_file_webp_metadata.py
index cb133e2c5..681d6fe7e 100644
--- a/Tests/test_file_webp_metadata.py
+++ b/Tests/test_file_webp_metadata.py
@@ -4,7 +4,8 @@ import pytest
 
 from PIL import Image
 
-from .helper import skip_unless_feature
+from .helper import skip_unless_feature, mark_if_feature_version
+
 
 pytestmark = [
     skip_unless_feature("webp"),
@@ -41,7 +42,7 @@ def test_read_exif_metadata_without_prefix():
         assert exif[305] == "Adobe Photoshop CS6 (Macintosh)"
 
 
-@pytest.mark.valgrind_known_error(reason="Known Failing")
+@mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
 def test_write_exif_metadata():
     file_path = "Tests/images/flower.jpg"
     test_buffer = BytesIO()
@@ -74,7 +75,7 @@ def test_read_icc_profile():
             assert icc == expected_icc
 
 
-@pytest.mark.valgrind_known_error(reason="Known Failing")
+@mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
 def test_write_icc_metadata():
     file_path = "Tests/images/flower2.jpg"
     test_buffer = BytesIO()
@@ -92,7 +93,7 @@ def test_write_icc_metadata():
         assert webp_icc_profile == expected_icc_profile, "Webp ICC didn't match"
 
 
-@pytest.mark.valgrind_known_error(reason="Known Failing")
+@mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
 def test_read_no_exif():
     file_path = "Tests/images/flower.jpg"
     test_buffer = BytesIO()
diff --git a/Tests/test_image.py b/Tests/test_image.py
index 30d093e15..f7b51773c 100644
--- a/Tests/test_image.py
+++ b/Tests/test_image.py
@@ -17,6 +17,7 @@ from .helper import (
     hopper,
     is_win32,
     skip_unless_feature,
+    mark_if_feature_version,
 )
 
 
@@ -662,7 +663,7 @@ class TestImage:
 
             assert not fp.closed
 
-    @pytest.mark.valgrind_known_error(reason="Known Failing")
+    @mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
     def test_exif_jpeg(self, tmp_path):
         with Image.open("Tests/images/exif-72dpi-int.jpg") as im:  # Little endian
             exif = im.getexif()
diff --git a/Tests/test_image_resample.py b/Tests/test_image_resample.py
index 69449198e..33d67fc15 100644
--- a/Tests/test_image_resample.py
+++ b/Tests/test_image_resample.py
@@ -4,7 +4,8 @@ import pytest
 
 from PIL import Image, ImageDraw
 
-from .helper import assert_image_equal, assert_image_similar, hopper
+from .helper import assert_image_equal, assert_image_similar, hopper, mark_if_feature_version
+
 
 
 class TestImagingResampleVulnerability:
@@ -455,7 +456,7 @@ class TestCoreResampleBox:
                 tiled.paste(tile, (x0, y0))
         return tiled
 
-    @pytest.mark.valgrind_known_error(reason="Known Failing")
+    @mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
     def test_tiles(self):
         with Image.open("Tests/images/flower.jpg") as im:
             assert im.size == (480, 360)
@@ -466,7 +467,7 @@ class TestCoreResampleBox:
                 tiled = self.resize_tiled(im, dst_size, *tiles)
                 assert_image_similar(reference, tiled, 0.01)
 
-    @pytest.mark.valgrind_known_error(reason="Known Failing")
+    @mark_if_feature_version(pytest.mark.valgrind_known_error, 'libjpeg_turbo', '2.0', reason="Known Failing")
     def test_subsample(self):
         # This test shows advantages of the subpixel resizing
         # after supersampling (e.g. during JPEG decoding).
diff --git a/Tests/test_image_thumbnail.py b/Tests/test_image_thumbnail.py
index 6911ce460..dd140955d 100644
--- a/Tests/test_image_thumbnail.py
+++ b/Tests/test_image_thumbnail.py
@@ -88,6 +88,7 @@ def test_no_resize():
         assert im.size == (64, 64)
 
 
+# valgrind test is failing with memory allocated in libjpeg
 @pytest.mark.valgrind_known_error(reason="Known Failing")
 def test_DCT_scaling_edges():
     # Make an image with red borders and size (N * 8) + 1 to cross DCT grid