diff --git a/Tests/test_core_resources.py b/Tests/test_core_resources.py
index 385192a3cdc..9021a9fb36d 100644
--- a/Tests/test_core_resources.py
+++ b/Tests/test_core_resources.py
@@ -177,13 +177,14 @@ def test_units(self):
         Image._apply_env_variables({"PILLOW_BLOCK_SIZE": "2m"})
         assert Image.core.get_block_size() == 2 * 1024 * 1024
 
-    def test_warnings(self):
-        pytest.warns(
-            UserWarning, Image._apply_env_variables, {"PILLOW_ALIGNMENT": "15"}
-        )
-        pytest.warns(
-            UserWarning, Image._apply_env_variables, {"PILLOW_BLOCK_SIZE": "1024"}
-        )
-        pytest.warns(
-            UserWarning, Image._apply_env_variables, {"PILLOW_BLOCKS_MAX": "wat"}
-        )
+    @pytest.mark.parametrize(
+        "var",
+        (
+            {"PILLOW_ALIGNMENT": "15"},
+            {"PILLOW_BLOCK_SIZE": "1024"},
+            {"PILLOW_BLOCKS_MAX": "wat"},
+        ),
+    )
+    def test_warnings(self, var):
+        with pytest.warns(UserWarning):
+            Image._apply_env_variables(var)
diff --git a/Tests/test_decompression_bomb.py b/Tests/test_decompression_bomb.py
index 63071b78c9c..4fd02449c7d 100644
--- a/Tests/test_decompression_bomb.py
+++ b/Tests/test_decompression_bomb.py
@@ -36,12 +36,10 @@ def test_warning(self):
         Image.MAX_IMAGE_PIXELS = 128 * 128 - 1
         assert Image.MAX_IMAGE_PIXELS == 128 * 128 - 1
 
-        def open():
+        with pytest.warns(Image.DecompressionBombWarning):
             with Image.open(TEST_FILE):
                 pass
 
-        pytest.warns(Image.DecompressionBombWarning, open)
-
     def test_exception(self):
         # Set limit to trigger exception on the test file
         Image.MAX_IMAGE_PIXELS = 64 * 128 - 1
@@ -87,7 +85,8 @@ def test_enlarge_crop(self):
         # same decompression bomb warnings on them.
         with hopper() as src:
             box = (0, 0, src.width * 2, src.height * 2)
-            pytest.warns(Image.DecompressionBombWarning, src.crop, box)
+            with pytest.warns(Image.DecompressionBombWarning):
+                src.crop(box)
 
     def test_crop_decompression_checks(self):
         im = Image.new("RGB", (100, 100))
@@ -95,7 +94,8 @@ def test_crop_decompression_checks(self):
         for value in ((-9999, -9999, -9990, -9990), (-999, -999, -990, -990)):
             assert im.crop(value).size == (9, 9)
 
-        pytest.warns(Image.DecompressionBombWarning, im.crop, (-160, -160, 99, 99))
+        with pytest.warns(Image.DecompressionBombWarning):
+            im.crop((-160, -160, 99, 99))
 
         with pytest.raises(Image.DecompressionBombError):
             im.crop((-99909, -99990, 99999, 99999))
diff --git a/Tests/test_file_apng.py b/Tests/test_file_apng.py
index 51637c78645..b2bec598496 100644
--- a/Tests/test_file_apng.py
+++ b/Tests/test_file_apng.py
@@ -263,13 +263,11 @@ def test_apng_chunk_errors():
     with Image.open("Tests/images/apng/chunk_no_actl.png") as im:
         assert not im.is_animated
 
-    def open():
+    with pytest.warns(UserWarning):
         with Image.open("Tests/images/apng/chunk_multi_actl.png") as im:
             im.load()
         assert not im.is_animated
 
-    pytest.warns(UserWarning, open)
-
     with Image.open("Tests/images/apng/chunk_actl_after_idat.png") as im:
         assert not im.is_animated
 
@@ -287,21 +285,17 @@ def open():
 
 
 def test_apng_syntax_errors():
-    def open_frames_zero():
+    with pytest.warns(UserWarning):
         with Image.open("Tests/images/apng/syntax_num_frames_zero.png") as im:
             assert not im.is_animated
             with pytest.raises(OSError):
                 im.load()
 
-    pytest.warns(UserWarning, open_frames_zero)
-
-    def open_frames_zero_default():
+    with pytest.warns(UserWarning):
         with Image.open("Tests/images/apng/syntax_num_frames_zero_default.png") as im:
             assert not im.is_animated
             im.load()
 
-    pytest.warns(UserWarning, open_frames_zero_default)
-
     # we can handle this case gracefully
     exception = None
     with Image.open("Tests/images/apng/syntax_num_frames_low.png") as im:
@@ -316,13 +310,11 @@ def open_frames_zero_default():
             im.seek(im.n_frames - 1)
             im.load()
 
-    def open():
+    with pytest.warns(UserWarning):
         with Image.open("Tests/images/apng/syntax_num_frames_invalid.png") as im:
             assert not im.is_animated
             im.load()
 
-    pytest.warns(UserWarning, open)
-
 
 @pytest.mark.parametrize(
     "test_file",
diff --git a/Tests/test_file_dcx.py b/Tests/test_file_dcx.py
index ef378b24a91..22686af3485 100644
--- a/Tests/test_file_dcx.py
+++ b/Tests/test_file_dcx.py
@@ -28,7 +28,8 @@ def open():
         im = Image.open(TEST_FILE)
         im.load()
 
-    pytest.warns(ResourceWarning, open)
+    with pytest.warns(ResourceWarning):
+        open()
 
 
 def test_closed_file():
diff --git a/Tests/test_file_fli.py b/Tests/test_file_fli.py
index 70d4d76db94..f96afdc95be 100644
--- a/Tests/test_file_fli.py
+++ b/Tests/test_file_fli.py
@@ -36,7 +36,8 @@ def open():
         im = Image.open(static_test_file)
         im.load()
 
-    pytest.warns(ResourceWarning, open)
+    with pytest.warns(ResourceWarning):
+        open()
 
 
 def test_closed_file():
diff --git a/Tests/test_file_gif.py b/Tests/test_file_gif.py
index bce72d1927d..8522f486aff 100644
--- a/Tests/test_file_gif.py
+++ b/Tests/test_file_gif.py
@@ -36,7 +36,8 @@ def open():
         im = Image.open(TEST_GIF)
         im.load()
 
-    pytest.warns(ResourceWarning, open)
+    with pytest.warns(ResourceWarning):
+        open()
 
 
 def test_closed_file():
@@ -1087,7 +1088,8 @@ def test_rgb_transparency(tmp_path):
     im = Image.new("RGB", (1, 1))
     im.info["transparency"] = b""
     ims = [Image.new("RGB", (1, 1))]
-    pytest.warns(UserWarning, im.save, out, save_all=True, append_images=ims)
+    with pytest.warns(UserWarning):
+        im.save(out, save_all=True, append_images=ims)
 
     with Image.open(out) as reloaded:
         assert "transparency" not in reloaded.info
diff --git a/Tests/test_file_ico.py b/Tests/test_file_ico.py
index 9c1c3cf170e..4e6dbe6ede4 100644
--- a/Tests/test_file_ico.py
+++ b/Tests/test_file_ico.py
@@ -212,12 +212,10 @@ def test_save_append_images(tmp_path):
 def test_unexpected_size():
     # This image has been manually hexedited to state that it is 16x32
     # while the image within is still 16x16
-    def open():
+    with pytest.warns(UserWarning):
         with Image.open("Tests/images/hopper_unexpected.ico") as im:
             assert im.size == (16, 16)
 
-    pytest.warns(UserWarning, open)
-
 
 def test_draw_reloaded(tmp_path):
     with Image.open(TEST_ICO_FILE) as im:
diff --git a/Tests/test_file_im.py b/Tests/test_file_im.py
index 425e690d66b..fd00f260e78 100644
--- a/Tests/test_file_im.py
+++ b/Tests/test_file_im.py
@@ -32,7 +32,8 @@ def open():
         im = Image.open(TEST_IM)
         im.load()
 
-    pytest.warns(ResourceWarning, open)
+    with pytest.warns(ResourceWarning):
+        open()
 
 
 def test_closed_file():
diff --git a/Tests/test_file_mpo.py b/Tests/test_file_mpo.py
index f0dedc2defc..2e921e46701 100644
--- a/Tests/test_file_mpo.py
+++ b/Tests/test_file_mpo.py
@@ -42,7 +42,8 @@ def open():
         im = Image.open(test_files[0])
         im.load()
 
-    pytest.warns(ResourceWarning, open)
+    with pytest.warns(ResourceWarning):
+        open()
 
 
 def test_closed_file():
diff --git a/Tests/test_file_psd.py b/Tests/test_file_psd.py
index 036cb9d4be5..e405834b5ca 100644
--- a/Tests/test_file_psd.py
+++ b/Tests/test_file_psd.py
@@ -27,7 +27,8 @@ def open():
         im = Image.open(test_file)
         im.load()
 
-    pytest.warns(ResourceWarning, open)
+    with pytest.warns(ResourceWarning):
+        open()
 
 
 def test_closed_file():
diff --git a/Tests/test_file_spider.py b/Tests/test_file_spider.py
index 011e208d8d8..09f1ef8e4a6 100644
--- a/Tests/test_file_spider.py
+++ b/Tests/test_file_spider.py
@@ -25,7 +25,8 @@ def open():
         im = Image.open(TEST_FILE)
         im.load()
 
-    pytest.warns(ResourceWarning, open)
+    with pytest.warns(ResourceWarning):
+        open()
 
 
 def test_closed_file():
diff --git a/Tests/test_file_tar.py b/Tests/test_file_tar.py
index 799c243d655..b27fa25f3e0 100644
--- a/Tests/test_file_tar.py
+++ b/Tests/test_file_tar.py
@@ -29,11 +29,9 @@ def test_sanity(codec, test_path, format):
 
 @pytest.mark.skipif(is_pypy(), reason="Requires CPython")
 def test_unclosed_file():
-    def open():
+    with pytest.warns(ResourceWarning):
         TarIO.TarIO(TEST_TAR_FILE, "hopper.jpg")
 
-    pytest.warns(ResourceWarning, open)
-
 
 def test_close():
     with warnings.catch_warnings():
diff --git a/Tests/test_file_tga.py b/Tests/test_file_tga.py
index bac00e8554a..1a5730f49d9 100644
--- a/Tests/test_file_tga.py
+++ b/Tests/test_file_tga.py
@@ -163,7 +163,9 @@ def test_save_id_section(tmp_path):
 
     # Save with custom id section greater than 255 characters
     id_section = b"Test content" * 25
-    pytest.warns(UserWarning, lambda: im.save(out, id_section=id_section))
+    with pytest.warns(UserWarning):
+        im.save(out, id_section=id_section)
+
     with Image.open(out) as test_im:
         assert test_im.info["id_section"] == id_section[:255]
 
diff --git a/Tests/test_file_tiff.py b/Tests/test_file_tiff.py
index 70142747ca2..b40f690f557 100644
--- a/Tests/test_file_tiff.py
+++ b/Tests/test_file_tiff.py
@@ -61,7 +61,8 @@ def open():
             im = Image.open("Tests/images/multipage.tiff")
             im.load()
 
-        pytest.warns(ResourceWarning, open)
+        with pytest.warns(ResourceWarning):
+            open()
 
     def test_closed_file(self):
         with warnings.catch_warnings():
@@ -231,7 +232,8 @@ def test_invalid_file(self):
     def test_bad_exif(self):
         with Image.open("Tests/images/hopper_bad_exif.jpg") as i:
             # Should not raise struct.error.
-            pytest.warns(UserWarning, i._getexif)
+            with pytest.warns(UserWarning):
+                i._getexif()
 
     def test_save_rgba(self, tmp_path):
         im = hopper("RGBA")
diff --git a/Tests/test_file_tiff_metadata.py b/Tests/test_file_tiff_metadata.py
index fdabae3a38a..b7d100e7a05 100644
--- a/Tests/test_file_tiff_metadata.py
+++ b/Tests/test_file_tiff_metadata.py
@@ -252,7 +252,8 @@ def test_empty_metadata():
     head = f.read(8)
     info = TiffImagePlugin.ImageFileDirectory(head)
     # Should not raise struct.error.
-    pytest.warns(UserWarning, info.load, f)
+    with pytest.warns(UserWarning):
+        info.load(f)
 
 
 def test_iccprofile(tmp_path):
@@ -418,11 +419,12 @@ def test_too_many_entries():
     ifd = TiffImagePlugin.ImageFileDirectory_v2()
 
     #    277: ("SamplesPerPixel", SHORT, 1),
-    ifd._tagdata[277] = struct.pack("hh", 4, 4)
+    ifd._tagdata[277] = struct.pack("<hh", 4, 4)
     ifd.tagtype[277] = TiffTags.SHORT
 
     # Should not raise ValueError.
-    pytest.warns(UserWarning, lambda: ifd[277])
+    with pytest.warns(UserWarning):
+        assert ifd[277] == 4
 
 
 def test_tag_group_data():
diff --git a/Tests/test_file_webp.py b/Tests/test_file_webp.py
index f1bdc59cf34..a7b6c735a69 100644
--- a/Tests/test_file_webp.py
+++ b/Tests/test_file_webp.py
@@ -29,7 +29,10 @@ def test_unsupported(self):
             WebPImagePlugin.SUPPORTED = False
 
         file_path = "Tests/images/hopper.webp"
-        pytest.warns(UserWarning, lambda: pytest.raises(OSError, Image.open, file_path))
+        with pytest.warns(UserWarning):
+            with pytest.raises(OSError):
+                with Image.open(file_path):
+                    pass
 
         if HAVE_WEBP:
             WebPImagePlugin.SUPPORTED = True
diff --git a/Tests/test_imagefont.py b/Tests/test_imagefont.py
index 306a2f1bff6..b115517acba 100644
--- a/Tests/test_imagefont.py
+++ b/Tests/test_imagefont.py
@@ -351,7 +351,8 @@ def test_rotated_transposed_font(font, orientation):
     assert bbox_b[3] == 20 + bbox_a[2] - bbox_a[0]
 
     # text length is undefined for vertical text
-    pytest.raises(ValueError, draw.textlength, word)
+    with pytest.raises(ValueError):
+        draw.textlength(word)
 
 
 @pytest.mark.parametrize(
@@ -872,25 +873,23 @@ def test_anchor_invalid(font):
     d.font = font
 
     for anchor in ["", "l", "a", "lax", "sa", "xa", "lx"]:
-        pytest.raises(ValueError, lambda: font.getmask2("hello", anchor=anchor))
-        pytest.raises(ValueError, lambda: font.getbbox("hello", anchor=anchor))
-        pytest.raises(ValueError, lambda: d.text((0, 0), "hello", anchor=anchor))
-        pytest.raises(ValueError, lambda: d.textbbox((0, 0), "hello", anchor=anchor))
-        pytest.raises(
-            ValueError, lambda: d.multiline_text((0, 0), "foo\nbar", anchor=anchor)
-        )
-        pytest.raises(
-            ValueError,
-            lambda: d.multiline_textbbox((0, 0), "foo\nbar", anchor=anchor),
-        )
+        with pytest.raises(ValueError):
+            font.getmask2("hello", anchor=anchor)
+        with pytest.raises(ValueError):
+            font.getbbox("hello", anchor=anchor)
+        with pytest.raises(ValueError):
+            d.text((0, 0), "hello", anchor=anchor)
+        with pytest.raises(ValueError):
+            d.textbbox((0, 0), "hello", anchor=anchor)
+        with pytest.raises(ValueError):
+            d.multiline_text((0, 0), "foo\nbar", anchor=anchor)
+        with pytest.raises(ValueError):
+            d.multiline_textbbox((0, 0), "foo\nbar", anchor=anchor)
     for anchor in ["lt", "lb"]:
-        pytest.raises(
-            ValueError, lambda: d.multiline_text((0, 0), "foo\nbar", anchor=anchor)
-        )
-        pytest.raises(
-            ValueError,
-            lambda: d.multiline_textbbox((0, 0), "foo\nbar", anchor=anchor),
-        )
+        with pytest.raises(ValueError):
+            d.multiline_text((0, 0), "foo\nbar", anchor=anchor)
+        with pytest.raises(ValueError):
+            d.multiline_textbbox((0, 0), "foo\nbar", anchor=anchor)
 
 
 @pytest.mark.parametrize("bpp", (1, 2, 4, 8))
diff --git a/Tests/test_imagefontctl.py b/Tests/test_imagefontctl.py
index cf039e86e61..6099b04e44b 100644
--- a/Tests/test_imagefontctl.py
+++ b/Tests/test_imagefontctl.py
@@ -360,37 +360,20 @@ def test_anchor_invalid_ttb():
     d.font = font
 
     for anchor in ["", "l", "a", "lax", "xa", "la", "ls", "ld", "lx"]:
-        pytest.raises(
-            ValueError, lambda: font.getmask2("hello", anchor=anchor, direction="ttb")
-        )
-        pytest.raises(
-            ValueError, lambda: font.getbbox("hello", anchor=anchor, direction="ttb")
-        )
-        pytest.raises(
-            ValueError, lambda: d.text((0, 0), "hello", anchor=anchor, direction="ttb")
-        )
-        pytest.raises(
-            ValueError,
-            lambda: d.textbbox((0, 0), "hello", anchor=anchor, direction="ttb"),
-        )
-        pytest.raises(
-            ValueError,
-            lambda: d.multiline_text(
-                (0, 0), "foo\nbar", anchor=anchor, direction="ttb"
-            ),
-        )
-        pytest.raises(
-            ValueError,
-            lambda: d.multiline_textbbox(
-                (0, 0), "foo\nbar", anchor=anchor, direction="ttb"
-            ),
-        )
+        with pytest.raises(ValueError):
+            font.getmask2("hello", anchor=anchor, direction="ttb")
+        with pytest.raises(ValueError):
+            font.getbbox("hello", anchor=anchor, direction="ttb")
+        with pytest.raises(ValueError):
+            d.text((0, 0), "hello", anchor=anchor, direction="ttb")
+        with pytest.raises(ValueError):
+            d.textbbox((0, 0), "hello", anchor=anchor, direction="ttb")
+        with pytest.raises(ValueError):
+            d.multiline_text((0, 0), "foo\nbar", anchor=anchor, direction="ttb")
+        with pytest.raises(ValueError):
+            d.multiline_textbbox((0, 0), "foo\nbar", anchor=anchor, direction="ttb")
     # ttb multiline text does not support anchors at all
-    pytest.raises(
-        ValueError,
-        lambda: d.multiline_text((0, 0), "foo\nbar", anchor="mm", direction="ttb"),
-    )
-    pytest.raises(
-        ValueError,
-        lambda: d.multiline_textbbox((0, 0), "foo\nbar", anchor="mm", direction="ttb"),
-    )
+    with pytest.raises(ValueError):
+        d.multiline_text((0, 0), "foo\nbar", anchor="mm", direction="ttb")
+    with pytest.raises(ValueError):
+        d.multiline_textbbox((0, 0), "foo\nbar", anchor="mm", direction="ttb")