diff --git a/Tests/bench_cffi_access.py b/Tests/bench_cffi_access.py
index 1797d34fc..8b172343c 100644
--- a/Tests/bench_cffi_access.py
+++ b/Tests/bench_cffi_access.py
@@ -49,7 +49,7 @@ class BenchCffiAccess(PillowTestCase):
         caccess = im.im.pixel_access(False)
         access = PyAccess.new(im, False)
 
-        self.assertEqual(caccess[(0, 0)], access[(0, 0)])
+        assert caccess[(0, 0)] == access[(0, 0)]
 
         print("Size: %sx%s" % im.size)
         timer(iterate_get, "PyAccess - get", im.size, access)
diff --git a/Tests/check_imaging_leaks.py b/Tests/check_imaging_leaks.py
index 2c1793a4f..8ca955ac7 100755
--- a/Tests/check_imaging_leaks.py
+++ b/Tests/check_imaging_leaks.py
@@ -26,7 +26,7 @@ class TestImagingLeaks(PillowTestCase):
                 mem_limit = mem + 1
                 continue
             msg = "memory usage limit exceeded after %d iterations" % (i + 1)
-            self.assertLessEqual(mem, mem_limit, msg)
+            assert mem <= mem_limit, msg
 
     def test_leak_putdata(self):
         im = Image.new("RGB", (25, 25))
diff --git a/Tests/test_color_lut.py b/Tests/test_color_lut.py
index 82a3bd1aa..6f8cb05b7 100644
--- a/Tests/test_color_lut.py
+++ b/Tests/test_color_lut.py
@@ -42,37 +42,37 @@ class TestColorLut3DCoreAPI(PillowTestCase):
     def test_wrong_args(self):
         im = Image.new("RGB", (10, 10), 0)
 
-        with self.assertRaisesRegex(ValueError, "filter"):
+        with pytest.raises(ValueError, match="filter"):
             im.im.color_lut_3d("RGB", Image.CUBIC, *self.generate_identity_table(3, 3))
 
-        with self.assertRaisesRegex(ValueError, "image mode"):
+        with pytest.raises(ValueError, match="image mode"):
             im.im.color_lut_3d(
                 "wrong", Image.LINEAR, *self.generate_identity_table(3, 3)
             )
 
-        with self.assertRaisesRegex(ValueError, "table_channels"):
+        with pytest.raises(ValueError, match="table_channels"):
             im.im.color_lut_3d("RGB", Image.LINEAR, *self.generate_identity_table(5, 3))
 
-        with self.assertRaisesRegex(ValueError, "table_channels"):
+        with pytest.raises(ValueError, match="table_channels"):
             im.im.color_lut_3d("RGB", Image.LINEAR, *self.generate_identity_table(1, 3))
 
-        with self.assertRaisesRegex(ValueError, "table_channels"):
+        with pytest.raises(ValueError, match="table_channels"):
             im.im.color_lut_3d("RGB", Image.LINEAR, *self.generate_identity_table(2, 3))
 
-        with self.assertRaisesRegex(ValueError, "Table size"):
+        with pytest.raises(ValueError, match="Table size"):
             im.im.color_lut_3d(
                 "RGB", Image.LINEAR, *self.generate_identity_table(3, (1, 3, 3))
             )
 
-        with self.assertRaisesRegex(ValueError, "Table size"):
+        with pytest.raises(ValueError, match="Table size"):
             im.im.color_lut_3d(
                 "RGB", Image.LINEAR, *self.generate_identity_table(3, (66, 3, 3))
             )
 
-        with self.assertRaisesRegex(ValueError, r"size1D \* size2D \* size3D"):
+        with pytest.raises(ValueError, match=r"size1D \* size2D \* size3D"):
             im.im.color_lut_3d("RGB", Image.LINEAR, 3, 2, 2, 2, [0, 0, 0] * 7)
 
-        with self.assertRaisesRegex(ValueError, r"size1D \* size2D \* size3D"):
+        with pytest.raises(ValueError, match=r"size1D \* size2D \* size3D"):
             im.im.color_lut_3d("RGB", Image.LINEAR, 3, 2, 2, 2, [0, 0, 0] * 9)
 
         with pytest.raises(TypeError):
@@ -105,25 +105,25 @@ class TestColorLut3DCoreAPI(PillowTestCase):
         )
 
     def test_wrong_mode(self):
-        with self.assertRaisesRegex(ValueError, "wrong mode"):
+        with pytest.raises(ValueError, match="wrong mode"):
             im = Image.new("L", (10, 10), 0)
             im.im.color_lut_3d("RGB", Image.LINEAR, *self.generate_identity_table(3, 3))
 
-        with self.assertRaisesRegex(ValueError, "wrong mode"):
+        with pytest.raises(ValueError, match="wrong mode"):
             im = Image.new("RGB", (10, 10), 0)
             im.im.color_lut_3d("L", Image.LINEAR, *self.generate_identity_table(3, 3))
 
-        with self.assertRaisesRegex(ValueError, "wrong mode"):
+        with pytest.raises(ValueError, match="wrong mode"):
             im = Image.new("L", (10, 10), 0)
             im.im.color_lut_3d("L", Image.LINEAR, *self.generate_identity_table(3, 3))
 
-        with self.assertRaisesRegex(ValueError, "wrong mode"):
+        with pytest.raises(ValueError, match="wrong mode"):
             im = Image.new("RGB", (10, 10), 0)
             im.im.color_lut_3d(
                 "RGBA", Image.LINEAR, *self.generate_identity_table(3, 3)
             )
 
-        with self.assertRaisesRegex(ValueError, "wrong mode"):
+        with pytest.raises(ValueError, match="wrong mode"):
             im = Image.new("RGB", (10, 10), 0)
             im.im.color_lut_3d("RGB", Image.LINEAR, *self.generate_identity_table(4, 3))
 
@@ -273,31 +273,31 @@ class TestColorLut3DCoreAPI(PillowTestCase):
 
 class TestColorLut3DFilter(PillowTestCase):
     def test_wrong_args(self):
-        with self.assertRaisesRegex(ValueError, "should be either an integer"):
+        with pytest.raises(ValueError, match="should be either an integer"):
             ImageFilter.Color3DLUT("small", [1])
 
-        with self.assertRaisesRegex(ValueError, "should be either an integer"):
+        with pytest.raises(ValueError, match="should be either an integer"):
             ImageFilter.Color3DLUT((11, 11), [1])
 
-        with self.assertRaisesRegex(ValueError, r"in \[2, 65\] range"):
+        with pytest.raises(ValueError, match=r"in \[2, 65\] range"):
             ImageFilter.Color3DLUT((11, 11, 1), [1])
 
-        with self.assertRaisesRegex(ValueError, r"in \[2, 65\] range"):
+        with pytest.raises(ValueError, match=r"in \[2, 65\] range"):
             ImageFilter.Color3DLUT((11, 11, 66), [1])
 
-        with self.assertRaisesRegex(ValueError, "table should have .+ items"):
+        with pytest.raises(ValueError, match="table should have .+ items"):
             ImageFilter.Color3DLUT((3, 3, 3), [1, 1, 1])
 
-        with self.assertRaisesRegex(ValueError, "table should have .+ items"):
+        with pytest.raises(ValueError, match="table should have .+ items"):
             ImageFilter.Color3DLUT((3, 3, 3), [[1, 1, 1]] * 2)
 
-        with self.assertRaisesRegex(ValueError, "should have a length of 4"):
+        with pytest.raises(ValueError, match="should have a length of 4"):
             ImageFilter.Color3DLUT((3, 3, 3), [[1, 1, 1]] * 27, channels=4)
 
-        with self.assertRaisesRegex(ValueError, "should have a length of 3"):
+        with pytest.raises(ValueError, match="should have a length of 3"):
             ImageFilter.Color3DLUT((2, 2, 2), [[1, 1]] * 8)
 
-        with self.assertRaisesRegex(ValueError, "Only 3 or 4 output"):
+        with pytest.raises(ValueError, match="Only 3 or 4 output"):
             ImageFilter.Color3DLUT((2, 2, 2), [[1, 1]] * 8, channels=2)
 
     def test_convert_table(self):
@@ -320,7 +320,7 @@ class TestColorLut3DFilter(PillowTestCase):
     @unittest.skipIf(numpy is None, "Numpy is not installed")
     def test_numpy_sources(self):
         table = numpy.ones((5, 6, 7, 3), dtype=numpy.float16)
-        with self.assertRaisesRegex(ValueError, "should have either channels"):
+        with pytest.raises(ValueError, match="should have either channels"):
             lut = ImageFilter.Color3DLUT((5, 6, 7), table)
 
         table = numpy.ones((7, 6, 5, 3), dtype=numpy.float16)
@@ -359,12 +359,12 @@ class TestColorLut3DFilter(PillowTestCase):
 
         lut = ImageFilter.Color3DLUT.generate((7, 9, 11), lambda r, g, b: (r, g, b))
         lut.table = numpy.array(lut.table, dtype=numpy.float32)[:-1]
-        with self.assertRaisesRegex(ValueError, "should have table_channels"):
+        with pytest.raises(ValueError, match="should have table_channels"):
             im.filter(lut)
 
         lut = ImageFilter.Color3DLUT.generate((7, 9, 11), lambda r, g, b: (r, g, b))
         lut.table = numpy.array(lut.table, dtype=numpy.float32).reshape((7 * 9 * 11), 3)
-        with self.assertRaisesRegex(ValueError, "should have table_channels"):
+        with pytest.raises(ValueError, match="should have table_channels"):
             im.filter(lut)
 
         lut = ImageFilter.Color3DLUT.generate((7, 9, 11), lambda r, g, b: (r, g, b))
@@ -404,15 +404,15 @@ class TestColorLut3DFilter(PillowTestCase):
 
 class TestGenerateColorLut3D(PillowTestCase):
     def test_wrong_channels_count(self):
-        with self.assertRaisesRegex(ValueError, "3 or 4 output channels"):
+        with pytest.raises(ValueError, match="3 or 4 output channels"):
             ImageFilter.Color3DLUT.generate(
                 5, channels=2, callback=lambda r, g, b: (r, g, b)
             )
 
-        with self.assertRaisesRegex(ValueError, "should have either channels"):
+        with pytest.raises(ValueError, match="should have either channels"):
             ImageFilter.Color3DLUT.generate(5, lambda r, g, b: (r, g, b, r))
 
-        with self.assertRaisesRegex(ValueError, "should have either channels"):
+        with pytest.raises(ValueError, match="should have either channels"):
             ImageFilter.Color3DLUT.generate(
                 5, channels=4, callback=lambda r, g, b: (r, g, b)
             )
@@ -454,13 +454,13 @@ class TestTransformColorLut3D(PillowTestCase):
     def test_wrong_args(self):
         source = ImageFilter.Color3DLUT.generate(5, lambda r, g, b: (r, g, b))
 
-        with self.assertRaisesRegex(ValueError, "Only 3 or 4 output"):
+        with pytest.raises(ValueError, match="Only 3 or 4 output"):
             source.transform(lambda r, g, b: (r, g, b), channels=8)
 
-        with self.assertRaisesRegex(ValueError, "should have either channels"):
+        with pytest.raises(ValueError, match="should have either channels"):
             source.transform(lambda r, g, b: (r, g, b), channels=4)
 
-        with self.assertRaisesRegex(ValueError, "should have either channels"):
+        with pytest.raises(ValueError, match="should have either channels"):
             source.transform(lambda r, g, b: (r, g, b, 1))
 
         with pytest.raises(TypeError):
diff --git a/Tests/test_file_jpeg.py b/Tests/test_file_jpeg.py
index be1188a63..7a934fc16 100644
--- a/Tests/test_file_jpeg.py
+++ b/Tests/test_file_jpeg.py
@@ -1,4 +1,5 @@
 import os
+import re
 from io import BytesIO
 
 import pytest
@@ -42,7 +43,7 @@ class TestFileJpeg(PillowTestCase):
     def test_sanity(self):
 
         # internal version number
-        self.assertRegex(Image.core.jpeglib_version, r"\d+\.\d+$")
+        assert re.search(r"\d+\.\d+$", Image.core.jpeglib_version)
 
         with Image.open(TEST_FILE) as im:
             im.load()
diff --git a/Tests/test_file_jpeg2k.py b/Tests/test_file_jpeg2k.py
index 339b54c46..1a0e9a358 100644
--- a/Tests/test_file_jpeg2k.py
+++ b/Tests/test_file_jpeg2k.py
@@ -1,3 +1,4 @@
+import re
 from io import BytesIO
 
 import pytest
@@ -34,7 +35,7 @@ class TestFileJpeg2k(PillowTestCase):
 
     def test_sanity(self):
         # Internal version number
-        self.assertRegex(Image.core.jp2klib_version, r"\d+\.\d+\.\d+$")
+        assert re.search(r"\d+\.\d+\.\d+$", Image.core.jp2klib_version)
 
         with Image.open("Tests/images/test-card-lossless.jp2") as im:
             px = im.load()
diff --git a/Tests/test_file_libtiff.py b/Tests/test_file_libtiff.py
index 988effee7..175ae987f 100644
--- a/Tests/test_file_libtiff.py
+++ b/Tests/test_file_libtiff.py
@@ -295,7 +295,9 @@ class TestFileLibTiff(LibTiffTestCase):
                             and libtiff
                         ):
                             # libtiff does not support real RATIONALS
-                            self.assertAlmostEqual(float(reloaded_value), float(value))
+                            assert (
+                                round(abs(float(reloaded_value) - float(value)), 7) == 0
+                            )
                             continue
 
                         if libtiff and isinstance(value, bytes):
diff --git a/Tests/test_file_png.py b/Tests/test_file_png.py
index c434d836c..6fbb4e414 100644
--- a/Tests/test_file_png.py
+++ b/Tests/test_file_png.py
@@ -1,3 +1,4 @@
+import re
 import unittest
 import zlib
 from io import BytesIO
@@ -75,7 +76,7 @@ class TestFilePng(PillowTestCase):
     def test_sanity(self):
 
         # internal version number
-        self.assertRegex(Image.core.zlib_version, r"\d+\.\d+\.\d+(\.\d+)?$")
+        assert re.search(r"\d+\.\d+\.\d+(\.\d+)?$", Image.core.zlib_version)
 
         test_file = self.tempfile("temp.png")
 
diff --git a/Tests/test_file_tiff_metadata.py b/Tests/test_file_tiff_metadata.py
index a00bd1c73..5554a25e9 100644
--- a/Tests/test_file_tiff_metadata.py
+++ b/Tests/test_file_tiff_metadata.py
@@ -65,9 +65,9 @@ class TestFileTiffMetadata(PillowTestCase):
             assert loaded.tag_v2[ImageDescription] == reloaded_textdata
 
             loaded_float = loaded.tag[tag_ids["RollAngle"]][0]
-            self.assertAlmostEqual(loaded_float, floatdata, places=5)
+            assert round(abs(loaded_float - floatdata), 5) == 0
             loaded_double = loaded.tag[tag_ids["YawAngle"]][0]
-            self.assertAlmostEqual(loaded_double, doubledata)
+            assert round(abs(loaded_double - doubledata), 7) == 0
 
         # check with 2 element ImageJMetaDataByteCounts, issue #2006
 
diff --git a/Tests/test_image_access.py b/Tests/test_image_access.py
index 721b2e7fd..35d61f904 100644
--- a/Tests/test_image_access.py
+++ b/Tests/test_image_access.py
@@ -228,9 +228,8 @@ class TestCffi(AccessTest):
                 assert access[(x, y)] == caccess[(x, y)]
 
         # Access an out-of-range pixel
-        self.assertRaises(
-            ValueError, lambda: access[(access.xsize + 1, access.ysize + 1)]
-        )
+        with pytest.raises(ValueError):
+            access[(access.xsize + 1, access.ysize + 1)]
 
     def test_get_vs_c(self):
         rgb = hopper("RGB")
diff --git a/Tests/test_image_resample.py b/Tests/test_image_resample.py
index 7ed6fce07..d3813b90a 100644
--- a/Tests/test_image_resample.py
+++ b/Tests/test_image_resample.py
@@ -418,24 +418,24 @@ class CoreResampleBoxTest(PillowTestCase):
             im.resize((32, 32), resample, (20, 20, 20, 100))
             im.resize((32, 32), resample, (20, 20, 100, 20))
 
-            with self.assertRaisesRegex(TypeError, "must be sequence of length 4"):
+            with pytest.raises(TypeError, match="must be sequence of length 4"):
                 im.resize((32, 32), resample, (im.width, im.height))
 
-            with self.assertRaisesRegex(ValueError, "can't be negative"):
+            with pytest.raises(ValueError, match="can't be negative"):
                 im.resize((32, 32), resample, (-20, 20, 100, 100))
-            with self.assertRaisesRegex(ValueError, "can't be negative"):
+            with pytest.raises(ValueError, match="can't be negative"):
                 im.resize((32, 32), resample, (20, -20, 100, 100))
 
-            with self.assertRaisesRegex(ValueError, "can't be empty"):
+            with pytest.raises(ValueError, match="can't be empty"):
                 im.resize((32, 32), resample, (20.1, 20, 20, 100))
-            with self.assertRaisesRegex(ValueError, "can't be empty"):
+            with pytest.raises(ValueError, match="can't be empty"):
                 im.resize((32, 32), resample, (20, 20.1, 100, 20))
-            with self.assertRaisesRegex(ValueError, "can't be empty"):
+            with pytest.raises(ValueError, match="can't be empty"):
                 im.resize((32, 32), resample, (20.1, 20.1, 20, 20))
 
-            with self.assertRaisesRegex(ValueError, "can't exceed"):
+            with pytest.raises(ValueError, match="can't exceed"):
                 im.resize((32, 32), resample, (0, 0, im.width + 1, im.height))
-            with self.assertRaisesRegex(ValueError, "can't exceed"):
+            with pytest.raises(ValueError, match="can't exceed"):
                 im.resize((32, 32), resample, (0, 0, im.width, im.height + 1))
 
     def resize_tiled(self, im, dst_size, xtiles, ytiles):
@@ -480,7 +480,7 @@ class CoreResampleBoxTest(PillowTestCase):
 
         # error with box should be much smaller than without
         assert_image_similar(reference, with_box, 6)
-        with self.assertRaisesRegex(AssertionError, r"difference 29\."):
+        with pytest.raises(AssertionError, match=r"difference 29\."):
             assert_image_similar(reference, without_box, 5)
 
     def test_formats(self):
@@ -518,7 +518,7 @@ class CoreResampleBoxTest(PillowTestCase):
         ]:
             res = im.resize(size, Image.LANCZOS, box)
             assert res.size == size
-            with self.assertRaisesRegex(AssertionError, r"difference \d"):
+            with pytest.raises(AssertionError, match=r"difference \d"):
                 # check that the difference at least that much
                 assert_image_similar(
                     res, im.crop(box), 20, ">>> {} {}".format(size, box)
diff --git a/Tests/test_imagefont.py b/Tests/test_imagefont.py
index 29da67f08..690f624d3 100644
--- a/Tests/test_imagefont.py
+++ b/Tests/test_imagefont.py
@@ -66,7 +66,7 @@ class TestImageFont(PillowTestCase):
         )
 
     def test_sanity(self):
-        self.assertRegex(ImageFont.core.freetype2_version, r"\d+\.\d+\.\d+$")
+        assert re.search(r"\d+\.\d+\.\d+$", ImageFont.core.freetype2_version)
 
     def test_font_properties(self):
         ttf = self.get_font()