diff --git a/.github/workflows/clear_self_hosted_persistent_caches.yaml b/.github/workflows/clear_self_hosted_persistent_caches.yaml
index fb7fce9c7dd..50d69728c62 100644
--- a/.github/workflows/clear_self_hosted_persistent_caches.yaml
+++ b/.github/workflows/clear_self_hosted_persistent_caches.yaml
@@ -26,44 +26,6 @@ jobs:
       run: du -sh ~/.pex || true; rm -rf ~/.pex || true
     - name: df after
       run: df -h
-  clean_macos10_15_x86_64:
-    runs-on:
-    - self-hosted
-    - macOS-10.15-X64
-    steps:
-    - name: df before
-      run: df -h
-    - name: Deleting ~/Library/Caches
-      run: du -sh ~/Library/Caches || true; rm -rf ~/Library/Caches || true
-    - name: Deleting ~/.cache
-      run: du -sh ~/.cache || true; rm -rf ~/.cache || true
-    - name: Deleting ~/.nce
-      run: du -sh ~/.nce || true; rm -rf ~/.nce || true
-    - name: Deleting ~/.rustup
-      run: du -sh ~/.rustup || true; rm -rf ~/.rustup || true
-    - name: Deleting ~/.pex
-      run: du -sh ~/.pex || true; rm -rf ~/.pex || true
-    - name: df after
-      run: df -h
-  clean_macos11_arm64:
-    runs-on:
-    - self-hosted
-    - macOS-11-ARM64
-    steps:
-    - name: df before
-      run: df -h
-    - name: Deleting ~/Library/Caches
-      run: du -sh ~/Library/Caches || true; rm -rf ~/Library/Caches || true
-    - name: Deleting ~/.cache
-      run: du -sh ~/.cache || true; rm -rf ~/.cache || true
-    - name: Deleting ~/.nce
-      run: du -sh ~/.nce || true; rm -rf ~/.nce || true
-    - name: Deleting ~/.rustup
-      run: du -sh ~/.rustup || true; rm -rf ~/.rustup || true
-    - name: Deleting ~/.pex
-      run: du -sh ~/.pex || true; rm -rf ~/.pex || true
-    - name: df after
-      run: df -h
 name: Clear persistent caches on long-lived self-hosted runners
 'on':
   workflow_dispatch: {}
diff --git a/.github/workflows/release.yaml b/.github/workflows/release.yaml
index d55a2d670c3..15a3d558e28 100644
--- a/.github/workflows/release.yaml
+++ b/.github/workflows/release.yaml
@@ -183,24 +183,39 @@ jobs:
         \ needs.release_info.outputs.release-asset-upload-url }}?name=$(basename $WHL)\"\
         \ \\\n    --data-binary \"@$WHL\";\n"
     timeout-minutes: 90
-  build_wheels_macos10_15_x86_64:
+  build_wheels_macos13_x86_64:
     env:
       ACTIONS_ALLOW_USE_UNSECURE_NODE_VERSION: false
       PANTS_REMOTE_CACHE_READ: 'false'
       PANTS_REMOTE_CACHE_WRITE: 'false'
     if: github.repository_owner == 'pantsbuild'
-    name: Build wheels (macOS10-15-x86_64)
+    name: Build wheels (macOS13-x86_64)
     needs:
     - release_info
     runs-on:
-    - self-hosted
-    - macOS-10.15-X64
+    - macos-13
     steps:
     - name: Check out code
       uses: actions/checkout@v4
       with:
         fetch-depth: 10
         ref: ${{ needs.release_info.outputs.build-ref }}
+    - name: Set up Python 3.7, 3.8, 3.9, 3.10, 3.12, 3.13, 3.11
+      uses: actions/setup-python@v5
+      with:
+        python-version: '3.7
+
+          3.8
+
+          3.9
+
+          3.10
+
+          3.12
+
+          3.13
+
+          3.11'
     - name: Install Protoc
       uses: arduino/setup-protoc@9b1ee5b22b0a3f1feb8c2ff99b32c89b3c3191e9
       with:
@@ -211,7 +226,7 @@ jobs:
     - name: Cache Rust toolchain
       uses: actions/cache@v4
       with:
-        key: macOS10-15-x86_64-rustup-${{ hashFiles('src/rust/engine/rust-toolchain')
+        key: macOS13-x86_64-rustup-${{ hashFiles('src/rust/engine/rust-toolchain')
           }}-v2
         path: '~/.rustup/toolchains/1.82.0-*
 
@@ -248,7 +263,7 @@ jobs:
       name: Upload pants.log
       uses: actions/upload-artifact@v4
       with:
-        name: logs-wheels-and-pex-macOS10-15-x86_64
+        name: logs-wheels-and-pex-macOS13-x86_64
         overwrite: 'true'
         path: .pants.d/workdir/*.log
     - if: needs.release_info.outputs.is-release == 'true'
@@ -269,24 +284,35 @@ jobs:
         \ needs.release_info.outputs.release-asset-upload-url }}?name=$(basename $WHL)\"\
         \ \\\n    --data-binary \"@$WHL\";\n"
     timeout-minutes: 90
-  build_wheels_macos11_arm64:
+  build_wheels_macos14_arm64:
     env:
       ACTIONS_ALLOW_USE_UNSECURE_NODE_VERSION: false
       PANTS_REMOTE_CACHE_READ: 'false'
       PANTS_REMOTE_CACHE_WRITE: 'false'
     if: github.repository_owner == 'pantsbuild'
-    name: Build wheels (macOS11-ARM64)
+    name: Build wheels (macOS14-ARM64)
     needs:
     - release_info
     runs-on:
-    - self-hosted
-    - macOS-11-ARM64
+    - macos-14
     steps:
     - name: Check out code
       uses: actions/checkout@v4
       with:
         fetch-depth: 10
         ref: ${{ needs.release_info.outputs.build-ref }}
+    - name: Set up Python 3.9, 3.10, 3.12, 3.13, 3.11
+      uses: actions/setup-python@v5
+      with:
+        python-version: '3.9
+
+          3.10
+
+          3.12
+
+          3.13
+
+          3.11'
     - name: Install Protoc
       uses: arduino/setup-protoc@9b1ee5b22b0a3f1feb8c2ff99b32c89b3c3191e9
       with:
@@ -297,7 +323,7 @@ jobs:
     - name: Cache Rust toolchain
       uses: actions/cache@v4
       with:
-        key: macOS11-ARM64-rustup-${{ hashFiles('src/rust/engine/rust-toolchain')
+        key: macOS14-ARM64-rustup-${{ hashFiles('src/rust/engine/rust-toolchain')
           }}-v2
         path: '~/.rustup/toolchains/1.82.0-*
 
@@ -334,7 +360,7 @@ jobs:
       name: Upload pants.log
       uses: actions/upload-artifact@v4
       with:
-        name: logs-wheels-and-pex-macOS11-ARM64
+        name: logs-wheels-and-pex-macOS14-ARM64
         overwrite: 'true'
         path: .pants.d/workdir/*.log
     - if: needs.release_info.outputs.is-release == 'true'
@@ -363,8 +389,8 @@ jobs:
     needs:
     - build_wheels_linux_x86_64
     - build_wheels_linux_arm64
-    - build_wheels_macos10_15_x86_64
-    - build_wheels_macos11_arm64
+    - build_wheels_macos13_x86_64
+    - build_wheels_macos14_arm64
     - release_info
     runs-on: ubuntu-latest
     steps:
diff --git a/.github/workflows/test.yaml b/.github/workflows/test.yaml
index 8dbe8cc0e1f..8d472031ffb 100644
--- a/.github/workflows/test.yaml
+++ b/.github/workflows/test.yaml
@@ -218,16 +218,16 @@ jobs:
 
         ./cargo doc'
     timeout-minutes: 60
-  bootstrap_pants_macos12_x86_64:
+  bootstrap_pants_macos13_x86_64:
     env:
       PANTS_REMOTE_CACHE_READ: 'false'
       PANTS_REMOTE_CACHE_WRITE: 'false'
     if: (github.repository_owner == 'pantsbuild') && (needs.classify_changes.outputs.docs_only != 'true')
-    name: Bootstrap Pants, test Rust (macOS12-x86_64)
+    name: Bootstrap Pants, test Rust (macOS13-x86_64)
     needs:
     - classify_changes
     runs-on:
-    - macos-12
+    - macos-13
     steps:
     - name: Check out code
       uses: actions/checkout@v4
@@ -259,7 +259,7 @@ jobs:
     - name: Cache Rust toolchain
       uses: actions/cache@v4
       with:
-        key: macOS12-x86_64-rustup-${{ hashFiles('src/rust/engine/rust-toolchain') }}-v2
+        key: macOS13-x86_64-rustup-${{ hashFiles('src/rust/engine/rust-toolchain') }}-v2
         path: '~/.rustup/toolchains/1.82.0-*
 
           ~/.rustup/update-hashes
@@ -280,7 +280,7 @@ jobs:
     - name: Cache native engine
       uses: actions/cache@v4
       with:
-        key: macOS12-x86_64-engine-${{ steps.get-engine-hash.outputs.hash }}-v1
+        key: macOS13-x86_64-engine-${{ steps.get-engine-hash.outputs.hash }}-v1
         path: 'src/python/pants/bin/native_client
 
           src/python/pants/engine/internals/native_engine.so
@@ -305,13 +305,13 @@ jobs:
       name: Upload pants.log
       uses: actions/upload-artifact@v4
       with:
-        name: logs-bootstrap-macOS12-x86_64
+        name: logs-bootstrap-macOS13-x86_64
         overwrite: 'true'
         path: .pants.d/workdir/*.log
     - name: Upload native binaries
       uses: actions/upload-artifact@v4
       with:
-        name: native_binaries.${{ matrix.python-version }}.macOS12-x86_64
+        name: native_binaries.${{ matrix.python-version }}.macOS13-x86_64
         path: 'src/python/pants/bin/native_client
 
           src/python/pants/engine/internals/native_engine.so
@@ -461,7 +461,7 @@ jobs:
         overwrite: 'true'
         path: .pants.d/workdir/*.log
     timeout-minutes: 90
-  build_wheels_macos10_15_x86_64:
+  build_wheels_macos13_x86_64:
     env:
       ACTIONS_ALLOW_USE_UNSECURE_NODE_VERSION: false
       MODE: debug
@@ -469,17 +469,32 @@ jobs:
       PANTS_REMOTE_CACHE_WRITE: 'false'
     if: ((github.repository_owner == 'pantsbuild') && (needs.classify_changes.outputs.release == 'true' || needs.classify_changes.outputs.ci_config
       == 'true')) && (needs.classify_changes.outputs.docs_only != 'true')
-    name: Build wheels (macOS10-15-x86_64)
+    name: Build wheels (macOS13-x86_64)
     needs:
     - classify_changes
     runs-on:
-    - self-hosted
-    - macOS-10.15-X64
+    - macos-13
     steps:
     - name: Check out code
       uses: actions/checkout@v4
       with:
         fetch-depth: 10
+    - name: Set up Python 3.7, 3.8, 3.9, 3.10, 3.12, 3.13, 3.11
+      uses: actions/setup-python@v5
+      with:
+        python-version: '3.7
+
+          3.8
+
+          3.9
+
+          3.10
+
+          3.12
+
+          3.13
+
+          3.11'
     - name: Install Protoc
       uses: arduino/setup-protoc@9b1ee5b22b0a3f1feb8c2ff99b32c89b3c3191e9
       with:
@@ -490,7 +505,7 @@ jobs:
     - name: Cache Rust toolchain
       uses: actions/cache@v4
       with:
-        key: macOS10-15-x86_64-rustup-${{ hashFiles('src/rust/engine/rust-toolchain') }}-v2
+        key: macOS13-x86_64-rustup-${{ hashFiles('src/rust/engine/rust-toolchain') }}-v2
         path: '~/.rustup/toolchains/1.82.0-*
 
           ~/.rustup/update-hashes
@@ -526,11 +541,11 @@ jobs:
       name: Upload pants.log
       uses: actions/upload-artifact@v4
       with:
-        name: logs-wheels-and-pex-macOS10-15-x86_64
+        name: logs-wheels-and-pex-macOS13-x86_64
         overwrite: 'true'
         path: .pants.d/workdir/*.log
     timeout-minutes: 90
-  build_wheels_macos11_arm64:
+  build_wheels_macos14_arm64:
     env:
       ACTIONS_ALLOW_USE_UNSECURE_NODE_VERSION: false
       MODE: debug
@@ -538,17 +553,28 @@ jobs:
       PANTS_REMOTE_CACHE_WRITE: 'false'
     if: ((github.repository_owner == 'pantsbuild') && (needs.classify_changes.outputs.release == 'true' || needs.classify_changes.outputs.ci_config
       == 'true')) && (needs.classify_changes.outputs.docs_only != 'true')
-    name: Build wheels (macOS11-ARM64)
+    name: Build wheels (macOS14-ARM64)
     needs:
     - classify_changes
     runs-on:
-    - self-hosted
-    - macOS-11-ARM64
+    - macos-14
     steps:
     - name: Check out code
       uses: actions/checkout@v4
       with:
         fetch-depth: 10
+    - name: Set up Python 3.9, 3.10, 3.12, 3.13, 3.11
+      uses: actions/setup-python@v5
+      with:
+        python-version: '3.9
+
+          3.10
+
+          3.12
+
+          3.13
+
+          3.11'
     - name: Install Protoc
       uses: arduino/setup-protoc@9b1ee5b22b0a3f1feb8c2ff99b32c89b3c3191e9
       with:
@@ -559,7 +585,7 @@ jobs:
     - name: Cache Rust toolchain
       uses: actions/cache@v4
       with:
-        key: macOS11-ARM64-rustup-${{ hashFiles('src/rust/engine/rust-toolchain') }}-v2
+        key: macOS14-ARM64-rustup-${{ hashFiles('src/rust/engine/rust-toolchain') }}-v2
         path: '~/.rustup/toolchains/1.82.0-*
 
           ~/.rustup/update-hashes
@@ -595,7 +621,7 @@ jobs:
       name: Upload pants.log
       uses: actions/upload-artifact@v4
       with:
-        name: logs-wheels-and-pex-macOS11-ARM64
+        name: logs-wheels-and-pex-macOS14-ARM64
         overwrite: 'true'
         path: .pants.d/workdir/*.log
     timeout-minutes: 90
@@ -732,11 +758,11 @@ jobs:
     - check_release_notes
     - bootstrap_pants_linux_arm64
     - bootstrap_pants_linux_x86_64
-    - bootstrap_pants_macos12_x86_64
+    - bootstrap_pants_macos13_x86_64
     - build_wheels_linux_arm64
     - build_wheels_linux_x86_64
-    - build_wheels_macos10_15_x86_64
-    - build_wheels_macos11_arm64
+    - build_wheels_macos13_x86_64
+    - build_wheels_macos14_arm64
     - check_release_notes
     - classify_changes
     - lint_python
@@ -751,7 +777,7 @@ jobs:
     - test_python_linux_x86_64_7
     - test_python_linux_x86_64_8
     - test_python_linux_x86_64_9
-    - test_python_macos12_x86_64
+    - test_python_macos13_x86_64
     outputs:
       merge_ok: ${{ steps.set_merge_ok.outputs.merge_ok }}
     runs-on:
@@ -1839,16 +1865,16 @@ jobs:
         overwrite: 'true'
         path: .pants.d/workdir/*.log
     timeout-minutes: 90
-  test_python_macos12_x86_64:
+  test_python_macos13_x86_64:
     env:
       ARCHFLAGS: -arch x86_64
     if: (github.repository_owner == 'pantsbuild') && (needs.classify_changes.outputs.docs_only != 'true')
-    name: Test Python (macOS12-x86_64)
+    name: Test Python (macOS13-x86_64)
     needs:
-    - bootstrap_pants_macos12_x86_64
+    - bootstrap_pants_macos13_x86_64
     - classify_changes
     runs-on:
-    - macos-12
+    - macos-13
     steps:
     - name: Check out code
       uses: actions/checkout@v4
@@ -1859,6 +1885,10 @@ jobs:
       with:
         distribution: adopt
         java-version: '11'
+    - name: Install Go
+      uses: actions/setup-go@v5
+      with:
+        go-version: 1.19.5
     - name: Set up Python 3.7, 3.8, 3.9, 3.10, 3.12, 3.13, 3.11
       uses: actions/setup-python@v5
       with:
@@ -1878,7 +1908,7 @@ jobs:
     - name: Download native binaries
       uses: actions/download-artifact@v4
       with:
-        name: native_binaries.${{ matrix.python-version }}.macOS12-x86_64
+        name: native_binaries.${{ matrix.python-version }}.macOS13-x86_64
         path: src/python/pants
     - name: Make native-client runnable
       run: chmod +x src/python/pants/bin/native_client
@@ -1892,7 +1922,7 @@ jobs:
         AWS_SECRET_ACCESS_KEY: ${{ secrets.AWS_SECRET_ACCESS_KEY }}
       if: always()
       name: Upload test reports
-      run: 'export S3_DST=s3://logs.pantsbuild.org/test/reports/macOS12-x86_64/$(git show --no-patch --format=%cd --date=format:%Y-%m-%d)/${GITHUB_REF_NAME//\//_}/${GITHUB_RUN_ID}/${GITHUB_RUN_ATTEMPT}/${GITHUB_JOB}
+      run: 'export S3_DST=s3://logs.pantsbuild.org/test/reports/macOS13-x86_64/$(git show --no-patch --format=%cd --date=format:%Y-%m-%d)/${GITHUB_REF_NAME//\//_}/${GITHUB_RUN_ID}/${GITHUB_RUN_ATTEMPT}/${GITHUB_JOB}
 
         echo "Uploading test reports to ${S3_DST}"
 
@@ -1904,7 +1934,7 @@ jobs:
       name: Upload pants.log
       uses: actions/upload-artifact@v4
       with:
-        name: logs-python-test-macOS12-x86_64
+        name: logs-python-test-macOS13-x86_64
         overwrite: 'true'
         path: .pants.d/workdir/*.log
     timeout-minutes: 90
diff --git a/docs/notes/2.25.x.md b/docs/notes/2.25.x.md
index 196a5a73cee..edeb780a121 100644
--- a/docs/notes/2.25.x.md
+++ b/docs/notes/2.25.x.md
@@ -13,6 +13,8 @@ established for this purpose. This non-profit's only source of revenue is
 
 ### Deprecations
 
+- **macOS versions**: Pants v2.25 is now built and tested on newer macOS versions: 13 (x86-64, previously 10.15) and macOS 14 (arm64, previously 11). The deprecation of the older versions were announced in Pants 2.23 and 2.24, and are driven by Apple's support schedule; they also help reduce cost for the volunteer-driven Pantsbuild organisation. Using Pants on older versions may or may not work.
+
 ### General
 
 ### New Options System
diff --git a/src/python/pants/base/exception_sink_test.py b/src/python/pants/base/exception_sink_test.py
index 8ce58723768..12f2905767c 100644
--- a/src/python/pants/base/exception_sink_test.py
+++ b/src/python/pants/base/exception_sink_test.py
@@ -55,6 +55,7 @@ def test_set_invalid_log_location():
         Platform.macos_x86_64: (
             "The provided log location path at '/' is not writable or could not be created: "
             "[Errno 21] Is a directory: '/'.",
+            "Error opening fatal error log streams for log location '/': [Errno 30] Read-only file system",
         ),
         Platform.linux_arm64: (
             "Error opening fatal error log streams for log location '/': [Errno 13] Permission "
diff --git a/src/python/pants_release/generate_github_workflows.py b/src/python/pants_release/generate_github_workflows.py
index 9363d689d57..5d97ea344f9 100644
--- a/src/python/pants_release/generate_github_workflows.py
+++ b/src/python/pants_release/generate_github_workflows.py
@@ -60,21 +60,30 @@ def action(name: str) -> str:
 class Platform(Enum):
     LINUX_X86_64 = "Linux-x86_64"
     LINUX_ARM64 = "Linux-ARM64"
-    MACOS10_15_X86_64 = "macOS10-15-x86_64"
-    # the oldest version of macOS supported by GitHub self-hosted runners
-    MACOS12_X86_64 = "macOS12-x86_64"
-    MACOS11_ARM64 = "macOS11-ARM64"
+    MACOS13_X86_64 = "macOS13-x86_64"
+    MACOS14_ARM64 = "macOS14-ARM64"
 
 
-GITHUB_HOSTED = {Platform.LINUX_X86_64, Platform.MACOS12_X86_64}
-SELF_HOSTED = {Platform.LINUX_ARM64, Platform.MACOS10_15_X86_64, Platform.MACOS11_ARM64}
-# We control these runners, so we preinstall and expose python on them.
-HAS_PYTHON = {Platform.LINUX_ARM64, Platform.MACOS10_15_X86_64, Platform.MACOS11_ARM64}
-HAS_GO = {Platform.MACOS12_X86_64, Platform.MACOS10_15_X86_64, Platform.MACOS11_ARM64}
+GITHUB_HOSTED = {Platform.LINUX_X86_64, Platform.MACOS13_X86_64, Platform.MACOS14_ARM64}
+SELF_HOSTED = {Platform.LINUX_ARM64}
 CARGO_AUDIT_IGNORED_ADVISORY_IDS = (
     "RUSTSEC-2020-0128",  # returns a false positive on the cache crate, which is a local crate not a 3rd party crate
 )
 
+# We don't specify a patch version so that we get the latest, which comes pre-installed:
+#  https://github.com/actions/setup-python#available-versions-of-python
+# NOTE: The last entry becomes the default
+_BASE_PYTHON_VERSIONS = ["3.7", "3.8", "3.9", "3.10", "3.12", "3.13", "3.11"]
+
+PYTHON_VERSIONS_PER_PLATFORM = {
+    Platform.LINUX_X86_64: _BASE_PYTHON_VERSIONS,
+    Platform.MACOS13_X86_64: _BASE_PYTHON_VERSIONS,
+    # Python 3.7 or 3.8 aren't supported directly on arm64 macOS
+    Platform.MACOS14_ARM64: [v for v in _BASE_PYTHON_VERSIONS if v not in ("3.7", "3.8")],
+    # These runners have Python already installed
+    Platform.LINUX_ARM64: None,
+}
+
 
 def gha_expr(expr: str) -> str:
     """Properly quote GitHub Actions expressions.
@@ -107,11 +116,6 @@ def hash_files(path: str) -> str:
     f"{NATIVE_FILES_COMMON_PREFIX}/engine/internals/native_engine.so.metadata",
 ]
 
-# We don't specify a patch version so that we get the latest, which comes pre-installed:
-#  https://github.com/actions/setup-python#available-versions-of-python
-# NOTE: The last entry becomes the default
-PYTHON_VERSIONS = ["3.7", "3.8", "3.9", "3.10", "3.12", "3.13", "3.11"]
-
 DONT_SKIP_RUST = "needs.classify_changes.outputs.rust == 'true'"
 DONT_SKIP_WHEELS = "needs.classify_changes.outputs.release == 'true' || needs.classify_changes.outputs.ci_config == 'true'"
 IS_PANTS_OWNER = "github.repository_owner == 'pantsbuild'"
@@ -409,12 +413,10 @@ def runs_on(self) -> list[str]:
         # any platform-specific labels, so we don't run on future GH-hosted
         # platforms without realizing it.
         ret = ["self-hosted"] if self.platform in SELF_HOSTED else []
-        if self.platform == Platform.MACOS12_X86_64:
-            ret += ["macos-12"]
-        elif self.platform == Platform.MACOS11_ARM64:
-            ret += ["macOS-11-ARM64"]
-        elif self.platform == Platform.MACOS10_15_X86_64:
-            ret += ["macOS-10.15-X64"]
+        if self.platform == Platform.MACOS13_X86_64:
+            ret += ["macos-13"]
+        elif self.platform == Platform.MACOS14_ARM64:
+            ret += ["macos-14"]
         elif self.platform == Platform.LINUX_X86_64:
             ret += ["ubuntu-22.04"]
         elif self.platform == Platform.LINUX_ARM64:
@@ -430,11 +432,11 @@ def runs_on(self) -> list[str]:
 
     def platform_env(self):
         ret = {}
-        if self.platform in {Platform.MACOS10_15_X86_64, Platform.MACOS12_X86_64}:
+        if self.platform in {Platform.MACOS13_X86_64}:
             # Works around bad `-arch arm64` flag embedded in Xcode 12.x Python interpreters on
             # intel machines. See: https://github.com/giampaolo/psutil/issues/1832
             ret["ARCHFLAGS"] = "-arch x86_64"
-        if self.platform == Platform.MACOS11_ARM64:
+        if self.platform in {Platform.MACOS14_ARM64}:
             ret["ARCHFLAGS"] = "-arch arm64"
         if self.platform == Platform.LINUX_X86_64:
             # Currently we run Linux x86_64 CI on GitHub Actions-hosted hardware, and
@@ -447,10 +449,6 @@ def platform_env(self):
         return ret
 
     def wrap_cmd(self, cmd: str) -> str:
-        if self.platform == Platform.MACOS11_ARM64:
-            # The self-hosted M1 runner is an X86_64 binary that runs under Rosetta,
-            # so we have to explicitly change the arch for the subprocesses it spawns.
-            return f"arch -arm64 {cmd}"
         return cmd
 
     def native_binaries_upload(self) -> Step:
@@ -536,8 +534,9 @@ def bootstrap_caches(self) -> Sequence[Step]:
 
     def setup_pythons(self) -> Sequence[Step]:
         ret = []
-        if self.platform not in HAS_PYTHON:
-            ret.append(install_pythons(PYTHON_VERSIONS))
+        versions = PYTHON_VERSIONS_PER_PLATFORM[self.platform]
+        if versions is not None:
+            ret.append(install_pythons(versions))
         return ret
 
     def bootstrap_pants(self) -> Sequence[Step]:
@@ -731,7 +730,7 @@ def test_jobs(
             *checkout(),
             *(launch_bazel_remote() if with_remote_caching else []),
             install_jdk(),
-            *([install_go()] if helper.platform not in HAS_GO else []),
+            install_go(),
             *(
                 [download_apache_thrift()]
                 if helper.platform == Platform.LINUX_X86_64
@@ -793,8 +792,8 @@ def linux_arm64_test_jobs() -> Jobs:
     return jobs
 
 
-def macos12_x86_64_test_jobs() -> Jobs:
-    helper = Helper(Platform.MACOS12_X86_64)
+def macos13_x86_64_test_jobs() -> Jobs:
+    helper = Helper(Platform.MACOS13_X86_64)
     jobs = {
         helper.job_name("bootstrap_pants"): bootstrap_jobs(
             helper,
@@ -964,8 +963,8 @@ def build_wheels_jobs(*, for_deploy_ref: str | None = None, needs: list[str] | N
     return {
         **build_wheels_job(Platform.LINUX_X86_64, for_deploy_ref, needs),
         **build_wheels_job(Platform.LINUX_ARM64, for_deploy_ref, needs),
-        **build_wheels_job(Platform.MACOS10_15_X86_64, for_deploy_ref, needs),
-        **build_wheels_job(Platform.MACOS11_ARM64, for_deploy_ref, needs),
+        **build_wheels_job(Platform.MACOS13_X86_64, for_deploy_ref, needs),
+        **build_wheels_job(Platform.MACOS14_ARM64, for_deploy_ref, needs),
     }
 
 
@@ -982,7 +981,7 @@ def test_workflow_jobs() -> Jobs:
     }
     jobs.update(**linux_x86_64_test_jobs())
     jobs.update(**linux_arm64_test_jobs())
-    jobs.update(**macos12_x86_64_test_jobs())
+    jobs.update(**macos13_x86_64_test_jobs())
     jobs.update(**build_wheels_jobs())
     jobs.update(
         {