From 9cb36a91d026115734a5dd46f408983035e6c3c4 Mon Sep 17 00:00:00 2001
From: Andrew Murray <3112309+radarhere@users.noreply.github.com>
Date: Wed, 15 Oct 2025 18:53:49 +1100
Subject: [PATCH] Upgrade from macos-13 (#9212)

Co-authored-by: Andrew Murray <radarhere@users.noreply.github.com>
---
 .github/workflows/macos-install.sh       | 13 +------------
 .github/workflows/test.yml               |  2 +-
 .github/workflows/wheels-dependencies.sh |  6 +++++-
 .github/workflows/wheels.yml             |  8 ++++----
 docs/installation/platform-support.rst   |  6 +++---
 5 files changed, 14 insertions(+), 21 deletions(-)

diff --git a/.github/workflows/macos-install.sh b/.github/workflows/macos-install.sh
index 8060e0850..b114d4a23 100755
--- a/.github/workflows/macos-install.sh
+++ b/.github/workflows/macos-install.sh
@@ -2,21 +2,10 @@
 
 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/.github/workflows/test.yml b/.github/workflows/test.yml
index 8504e5c1e..b52000a27 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -57,7 +57,7 @@ jobs:
         - { python-version: "3.14t", disable-gil: true }
         - { python-version: "3.13t", disable-gil: true }
         # Intel
-        - { os: "macos-13", python-version: "3.10" }
+        - { os: "macos-15-intel", python-version: "3.10" }
         exclude:
         - { os: "macos-latest", python-version: "3.10" }
 
diff --git a/.github/workflows/wheels-dependencies.sh b/.github/workflows/wheels-dependencies.sh
index 69c867b4d..7d6eb8681 100755
--- a/.github/workflows/wheels-dependencies.sh
+++ b/.github/workflows/wheels-dependencies.sh
@@ -271,7 +271,11 @@ function build {
     if [ -z "$IS_ALPINE" ] && [ -z "$SANITIZER" ] && [ -z "$IS_MACOS" ]; then
         yum remove -y zlib-devel
     fi
-    build_zlib_ng
+    if [[ -n "$IS_MACOS" ]]; then
+        CFLAGS="$CFLAGS -headerpad_max_install_names" build_zlib_ng
+    else
+        build_zlib_ng
+    fi
 
     build_simple xcb-proto 1.17.0 https://xorg.freedesktop.org/archive/individual/proto
     if [[ -n "$IS_MACOS" ]]; then
diff --git a/.github/workflows/wheels.yml b/.github/workflows/wheels.yml
index eef70f894..6dc8db7e9 100644
--- a/.github/workflows/wheels.yml
+++ b/.github/workflows/wheels.yml
@@ -53,19 +53,19 @@ jobs:
         include:
           - name: "macOS 10.10 x86_64"
             platform: macos
-            os: macos-13
+            os: macos-15-intel
             cibw_arch: x86_64
             build: "cp3{10,11}*"
             macosx_deployment_target: "10.10"
           - name: "macOS 10.13 x86_64"
             platform: macos
-            os: macos-13
+            os: macos-15-intel
             cibw_arch: x86_64
             build: "cp3{12,13}*"
             macosx_deployment_target: "10.13"
           - name: "macOS 10.15 x86_64"
             platform: macos
-            os: macos-13
+            os: macos-15-intel
             cibw_arch: x86_64
             build: "{cp314,pp3}*"
             macosx_deployment_target: "10.15"
@@ -104,7 +104,7 @@ jobs:
             cibw_arch: arm64_iphonesimulator
           - name: "iOS x86_64 simulator"
             platform: ios
-            os: macos-13
+            os: macos-15-intel
             cibw_arch: x86_64_iphonesimulator
     steps:
       - uses: actions/checkout@v5
diff --git a/docs/installation/platform-support.rst b/docs/installation/platform-support.rst
index 186d9b96d..7999504fb 100644
--- a/docs/installation/platform-support.rst
+++ b/docs/installation/platform-support.rst
@@ -39,9 +39,9 @@ These platforms are built and tested for every change.
 +----------------------------------+----------------------------+---------------------+
 | Gentoo                           | 3.12                       | x86-64              |
 +----------------------------------+----------------------------+---------------------+
-| macOS 13 Ventura                 | 3.10                       | x86-64              |
-+----------------------------------+----------------------------+---------------------+
-| macOS 15 Sequoia                 | 3.11, 3.12, 3.13, 3.14     | arm64               |
+| macOS 15 Sequoia                 | 3.10                       | x86-64              |
+|                                  +----------------------------+---------------------+
+|                                  | 3.11, 3.12, 3.13, 3.14,    | arm64               |
 |                                  | PyPy3                      |                     |
 +----------------------------------+----------------------------+---------------------+
 | Ubuntu Linux 22.04 LTS (Jammy)   | 3.10                       | x86-64              |