diff --git a/requirements-production.txt b/requirements-production.txt
index 042c1fd3..8d2e0361 100644
--- a/requirements-production.txt
+++ b/requirements-production.txt
@@ -2,7 +2,7 @@ beautifulsoup4>=4.9.3,<5
 bleach>=3.2,<3.3
 Django>=4.0,<4.1
 Markdown>=3.0,<4
-Pillow>=8.0,<9
+Pillow>=9.3,<10
 boto3>=1.14,<1.15
 celery>=5.2,<5.3
 django-compressor>=3,<4
diff --git a/requirements.txt b/requirements.txt
index 38eb338e..5451bd22 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -3,7 +3,7 @@ bleach>=3.2,<3.3
 Django>=4.0,<4.1
 Fabric>=2.5,<2.6
 Markdown>=3.0,<4
-Pillow>=8.0,<9
+Pillow>=9.3,<10
 boto3>=1.14,<1.15
 celery>=5.2,<5.3
 django-compressor>=3,<4
diff --git a/screenshots/models.py b/screenshots/models.py
index cdb3093b..ee667ef7 100644
--- a/screenshots/models.py
+++ b/screenshots/models.py
@@ -79,9 +79,7 @@ def create_original(self):
 
     def create_thumbnail(self, target_size):
         img = self.image
-
-        if img.format == 'JPEG':
-            img = ImageOps.exif_transpose(img)
+        img = ImageOps.exif_transpose(img)
 
         crop_params, resize_params = get_thumbnail_sizing_params(img.size, target_size)
         if crop_params:
@@ -96,15 +94,15 @@ def create_thumbnail(self, target_size):
             # must ensure image is non-paletted for a high-quality resize
             if img.mode in ['1', 'P']:
                 img = img.convert('RGB')
-            img = img.resize(resize_params, Image.ANTIALIAS)
+            img = img.resize(resize_params, Image.Resampling.LANCZOS)
 
         output = io.BytesIO()
         if has_limited_palette:
             if img.mode not in ['1', 'P']:
-                # img.convert with palette=Image.ADAPTIVE will apparently only work on
+                # img.convert with palette=Image.Palette.ADAPTIVE will apparently only work on
                 # 'L' or 'RGB' images, not RGBA for example. So, need to pre-convert to RGB...
                 img = img.convert('RGB')
-                img = img.convert('P', palette=Image.ADAPTIVE, colors=256)
+                img = img.convert('P', palette=Image.Palette.ADAPTIVE, colors=256)
             img.save(output, format='PNG', optimize=True)
             return output, img.size, 'png'
         else:
diff --git a/screenshots/tests/images/bfield-standard.out.jpg b/screenshots/tests/images/bfield-standard.out.jpg
index 3d4d354f..9a5a6cc1 100644
Binary files a/screenshots/tests/images/bfield-standard.out.jpg and b/screenshots/tests/images/bfield-standard.out.jpg differ
diff --git a/screenshots/tests/images/twintris.out.jpg b/screenshots/tests/images/twintris.out.jpg
index 518cb0dc..0bca5f05 100644
Binary files a/screenshots/tests/images/twintris.out.jpg and b/screenshots/tests/images/twintris.out.jpg differ
diff --git a/screenshots/tests/test_conversion.py b/screenshots/tests/test_conversion.py
index d2d4415f..7f807d4a 100644
--- a/screenshots/tests/test_conversion.py
+++ b/screenshots/tests/test_conversion.py
@@ -21,7 +21,7 @@ def assertImagesSimilar(self, img1, img2):
         sum_squares = sum(sq)
         result = math.sqrt(sum_squares / float(image1.size[0] * image1.size[1]))
 
-        self.assertTrue(result < 1, "Images are too different")
+        self.assertTrue(result < 5, "Images are too different")
 
     def test_wmf(self):
         # WMF is not in our PIL_READABLE_FORMATS list