diff --git a/.github/workflows/macos-install.sh b/.github/workflows/macos-install.sh
index 94e3d5d08..8060e0850 100755
--- a/.github/workflows/macos-install.sh
+++ b/.github/workflows/macos-install.sh
@@ -4,11 +4,19 @@ set -e
 
 if [[ "$ImageOS" == "macos13" ]]; then
     brew uninstall gradle maven
+
+    wget https://raw.githubusercontent.com/python-pillow/pillow-depends/main/freetype-2.14.1.tar.gz
+    tar -xvzf freetype-2.14.1.tar.gz
+    (cd freetype-2.14.1 \
+        && ./configure \
+        && make -j4 \
+        && make install)
+else
+    brew install freetype
 fi
 brew install \
     aom \
     dav1d \
-    freetype \
     ghostscript \
     jpeg-turbo \
     libimagequant \
diff --git a/Tests/images/colr_bungee.png b/Tests/images/colr_bungee.png
index b10a60be0..9ec6b1182 100644
Binary files a/Tests/images/colr_bungee.png and b/Tests/images/colr_bungee.png differ
diff --git a/Tests/images/colr_bungee_mask.png b/Tests/images/colr_bungee_mask.png
index f13e17677..79106b639 100644
Binary files a/Tests/images/colr_bungee_mask.png and b/Tests/images/colr_bungee_mask.png differ
diff --git a/Tests/images/colr_bungee_older.png b/Tests/images/colr_bungee_older.png
new file mode 100644
index 000000000..b10a60be0
Binary files /dev/null and b/Tests/images/colr_bungee_older.png differ
diff --git a/Tests/test_imagedraw.py b/Tests/test_imagedraw.py
index 406d965b4..790acee2a 100644
--- a/Tests/test_imagedraw.py
+++ b/Tests/test_imagedraw.py
@@ -1494,7 +1494,9 @@ def test_default_font_size() -> None:
 
     def draw_text() -> None:
         draw.text((0, 0), text, font_size=16)
-        assert_image_equal_tofile(im, "Tests/images/imagedraw_default_font_size.png")
+        assert_image_similar_tofile(
+            im, "Tests/images/imagedraw_default_font_size.png", 1
+        )
 
     check(draw_text)
 
@@ -1513,7 +1515,9 @@ def test_default_font_size() -> None:
 
     def draw_multiline_text() -> None:
         draw.multiline_text((0, 0), text, font_size=16)
-        assert_image_equal_tofile(im, "Tests/images/imagedraw_default_font_size.png")
+        assert_image_similar_tofile(
+            im, "Tests/images/imagedraw_default_font_size.png", 1
+        )
 
     check(draw_multiline_text)
 
diff --git a/Tests/test_imagefont.py b/Tests/test_imagefont.py
index 4565d35ba..4b8a61eb3 100644
--- a/Tests/test_imagefont.py
+++ b/Tests/test_imagefont.py
@@ -19,6 +19,7 @@ from .helper import (
     assert_image_equal,
     assert_image_equal_tofile,
     assert_image_similar_tofile,
+    has_feature_version,
     is_win32,
     skip_unless_feature,
     skip_unless_feature_version,
@@ -549,7 +550,7 @@ def test_default_font() -> None:
     draw.text((10, 60), txt, font=larger_default_font)
 
     # Assert
-    assert_image_equal_tofile(im, "Tests/images/default_font_freetype.png")
+    assert_image_similar_tofile(im, "Tests/images/default_font_freetype.png", 0.13)
 
 
 @pytest.mark.parametrize("mode", ("", "1", "RGBA"))
@@ -1055,7 +1056,10 @@ def test_colr(layout_engine: ImageFont.Layout) -> None:
 
     d.text((15, 5), "Bungee", font=font, embedded_color=True)
 
-    assert_image_similar_tofile(im, "Tests/images/colr_bungee.png", 21)
+    if has_feature_version("freetype2", "2.14.0"):
+        assert_image_similar_tofile(im, "Tests/images/colr_bungee.png", 6.1)
+    else:
+        assert_image_similar_tofile(im, "Tests/images/colr_bungee_older.png", 21)
 
 
 @skip_unless_feature_version("freetype2", "2.10.0")
@@ -1071,7 +1075,7 @@ def test_colr_mask(layout_engine: ImageFont.Layout) -> None:
 
     d.text((15, 5), "Bungee", "black", font=font)
 
-    assert_image_similar_tofile(im, "Tests/images/colr_bungee_mask.png", 22)
+    assert_image_similar_tofile(im, "Tests/images/colr_bungee_mask.png", 14.1)
 
 
 def test_woff2(layout_engine: ImageFont.Layout) -> None:
diff --git a/Tests/test_imagefontctl.py b/Tests/test_imagefontctl.py
index 95af3fda8..633f6756b 100644
--- a/Tests/test_imagefontctl.py
+++ b/Tests/test_imagefontctl.py
@@ -183,7 +183,7 @@ def test_x_max_and_y_offset() -> None:
     draw.text((0, 0), "لح", font=ttf, fill=500)
 
     target = "Tests/images/test_x_max_and_y_offset.png"
-    assert_image_similar_tofile(im, target, 0.5)
+    assert_image_similar_tofile(im, target, 3.8)
 
 
 def test_language() -> None:
diff --git a/winbuild/build_prepare.py b/winbuild/build_prepare.py
index ba69878bc..5c638829e 100644
--- a/winbuild/build_prepare.py
+++ b/winbuild/build_prepare.py
@@ -114,7 +114,7 @@ ARCHITECTURES = {
 
 V = {
     "BROTLI": "1.1.0",
-    "FREETYPE": "2.13.3",
+    "FREETYPE": "2.14.1",
     "FRIBIDI": "1.0.16",
     "HARFBUZZ": "11.4.5",
     "JPEGTURBO": "3.1.2",