diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index 810490f735..c505fbf594 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -21,9 +21,6 @@ on:
       macos:
         default: true
         type: boolean
-      macos_legacy:
-        default: true
-        type: boolean
       windows:
         default: true
         type: boolean
@@ -67,10 +64,6 @@ on:
         description: yt-dlp_macos, yt-dlp_macos.zip
         default: true
         type: boolean
-      macos_legacy:
-        description: yt-dlp_macos_legacy
-        default: true
-        type: boolean
       windows:
         description: yt-dlp.exe, yt-dlp_win.zip
         default: true
@@ -344,58 +337,6 @@ jobs:
             ~/yt-dlp-build-venv
           key: cache-reqs-${{ github.job }}-${{ github.ref }}
 
-  macos_legacy:
-    needs: process
-    if: inputs.macos_legacy
-    runs-on: macos-13
-
-    steps:
-      - uses: actions/checkout@v4
-      - name: Install Python
-        # We need the official Python, because the GA ones only support newer macOS versions
-        env:
-          PYTHON_VERSION: 3.10.5
-          MACOSX_DEPLOYMENT_TARGET: 10.9 # Used up by the Python build tools
-        run: |
-          # Hack to get the latest patch version. Uncomment if needed
-          #brew install python@3.10
-          #export PYTHON_VERSION=$( $(brew --prefix)/opt/python@3.10/bin/python3 --version | cut -d ' ' -f 2 )
-          curl "https://www.python.org/ftp/python/${PYTHON_VERSION}/python-${PYTHON_VERSION}-macos11.pkg" -o "python.pkg"
-          sudo installer -pkg python.pkg -target /
-          python3 --version
-      - name: Install Requirements
-        run: |
-          brew install coreutils
-          python3 devscripts/install_deps.py --user -o --include build
-          python3 devscripts/install_deps.py --user --include pyinstaller
-
-      - name: Prepare
-        run: |
-          python3 devscripts/update-version.py -c "${{ inputs.channel }}" -r "${{ needs.process.outputs.origin }}" "${{ inputs.version }}"
-          python3 devscripts/make_lazy_extractors.py
-      - name: Build
-        run: |
-          python3 -m bundle.pyinstaller
-          mv dist/yt-dlp_macos dist/yt-dlp_macos_legacy
-
-      - name: Verify --update-to
-        if: vars.UPDATE_TO_VERIFICATION
-        run: |
-          chmod +x ./dist/yt-dlp_macos_legacy
-          cp ./dist/yt-dlp_macos_legacy ./dist/yt-dlp_macos_legacy_downgraded
-          version="$(./dist/yt-dlp_macos_legacy --version)"
-          ./dist/yt-dlp_macos_legacy_downgraded -v --update-to yt-dlp/yt-dlp@2023.03.04
-          downgraded_version="$(./dist/yt-dlp_macos_legacy_downgraded --version)"
-          [[ "$version" != "$downgraded_version" ]]
-
-      - name: Upload artifacts
-        uses: actions/upload-artifact@v4
-        with:
-          name: build-bin-${{ github.job }}
-          path: |
-            dist/yt-dlp_macos_legacy
-          compression-level: 0
-
   windows:
     needs: process
     if: inputs.windows
@@ -498,7 +439,6 @@ jobs:
       - linux_static
       - linux_arm
       - macos
-      - macos_legacy
       - windows
       - windows32
     runs-on: ubuntu-latest
@@ -532,6 +472,7 @@ jobs:
           lock 2024.10.22 linux_(?:armv7l|aarch64)_exe .+-glibc2\.(?:[12]?\d|30)\b
           lock 2024.10.22 (?!\w+_exe).+ Python 3\.8
           lock 2024.10.22 win(?:_x86)?_exe Python 3\.[78].+ Windows-(?:7-|2008ServerR2)
+          lock 2025.09.01 darwin_legacy_exe .+
           lockV2 yt-dlp/yt-dlp 2022.08.18.36 .+ Python 3\.6
           lockV2 yt-dlp/yt-dlp 2023.11.16 (?!win_x86_exe).+ Python 3\.7
           lockV2 yt-dlp/yt-dlp 2023.11.16 win_x86_exe .+ Windows-(?:Vista|2008Server)
@@ -539,18 +480,21 @@ jobs:
           lockV2 yt-dlp/yt-dlp 2024.10.22 linux_(?:armv7l|aarch64)_exe .+-glibc2\.(?:[12]?\d|30)\b
           lockV2 yt-dlp/yt-dlp 2024.10.22 (?!\w+_exe).+ Python 3\.8
           lockV2 yt-dlp/yt-dlp 2024.10.22 win(?:_x86)?_exe Python 3\.[78].+ Windows-(?:7-|2008ServerR2)
+          lockV2 yt-dlp/yt-dlp 2025.09.01 darwin_legacy_exe .+
           lockV2 yt-dlp/yt-dlp-nightly-builds 2023.11.15.232826 (?!win_x86_exe).+ Python 3\.7
           lockV2 yt-dlp/yt-dlp-nightly-builds 2023.11.15.232826 win_x86_exe .+ Windows-(?:Vista|2008Server)
           lockV2 yt-dlp/yt-dlp-nightly-builds 2024.10.22.051025 py2exe .+
           lockV2 yt-dlp/yt-dlp-nightly-builds 2024.10.22.051025 linux_(?:armv7l|aarch64)_exe .+-glibc2\.(?:[12]?\d|30)\b
           lockV2 yt-dlp/yt-dlp-nightly-builds 2024.10.22.051025 (?!\w+_exe).+ Python 3\.8
           lockV2 yt-dlp/yt-dlp-nightly-builds 2024.10.22.051025 win(?:_x86)?_exe Python 3\.[78].+ Windows-(?:7-|2008ServerR2)
+          lockV2 yt-dlp/yt-dlp-nightly-builds 2025.09.01.234000 darwin_legacy_exe .+
           lockV2 yt-dlp/yt-dlp-master-builds 2023.11.15.232812 (?!win_x86_exe).+ Python 3\.7
           lockV2 yt-dlp/yt-dlp-master-builds 2023.11.15.232812 win_x86_exe .+ Windows-(?:Vista|2008Server)
           lockV2 yt-dlp/yt-dlp-master-builds 2024.10.22.045052 py2exe .+
           lockV2 yt-dlp/yt-dlp-master-builds 2024.10.22.060347 linux_(?:armv7l|aarch64)_exe .+-glibc2\.(?:[12]?\d|30)\b
           lockV2 yt-dlp/yt-dlp-master-builds 2024.10.22.060347 (?!\w+_exe).+ Python 3\.8
           lockV2 yt-dlp/yt-dlp-master-builds 2024.10.22.060347 win(?:_x86)?_exe Python 3\.[78].+ Windows-(?:7-|2008ServerR2)
+          lockV2 yt-dlp/yt-dlp-master-builds 2025.09.01.000000 darwin_legacy_exe .+
           EOF
 
       - name: Sign checksum files
diff --git a/README.md b/README.md
index 9b28147f2c..aa8b1d4f24 100644
--- a/README.md
+++ b/README.md
@@ -111,7 +111,6 @@ #### Alternatives
 [yt-dlp_linux_aarch64](https://github.com/yt-dlp/yt-dlp/releases/latest/download/yt-dlp_linux_aarch64)|Linux standalone aarch64 (64-bit) binary
 [yt-dlp_win.zip](https://github.com/yt-dlp/yt-dlp/releases/latest/download/yt-dlp_win.zip)|Unpackaged Windows executable (no auto-update)
 [yt-dlp_macos.zip](https://github.com/yt-dlp/yt-dlp/releases/latest/download/yt-dlp_macos.zip)|Unpackaged MacOS (10.15+) executable (no auto-update)
-[yt-dlp_macos_legacy](https://github.com/yt-dlp/yt-dlp/releases/latest/download/yt-dlp_macos_legacy)|MacOS (10.9+) standalone x64 executable
 
 #### Misc
 
diff --git a/yt_dlp/update.py b/yt_dlp/update.py
index ca69fbbada..dd948cd521 100644
--- a/yt_dlp/update.py
+++ b/yt_dlp/update.py
@@ -58,26 +58,30 @@ def _get_variant_and_executable_path():
     """@returns (variant, executable_path)"""
     if getattr(sys, 'frozen', False):
         path = sys.executable
+        # py2exe is unsupported but we should still correctly identify it for debugging purposes
         if not hasattr(sys, '_MEIPASS'):
             return 'py2exe', path
-        elif sys._MEIPASS == os.path.dirname(path):
+        if sys._MEIPASS == os.path.dirname(path):
             return f'{sys.platform}_dir', path
-        elif sys.platform == 'darwin':
+        if sys.platform == 'darwin':
+            # darwin_legacy_exe is no longer supported, but still identify it to block updates
             machine = '_legacy' if version_tuple(platform.mac_ver()[0]) < (10, 15) else ''
-        else:
-            machine = f'_{platform.machine().lower()}'
-            is_64bits = sys.maxsize > 2**32
-            # Ref: https://en.wikipedia.org/wiki/Uname#Examples
-            if machine[1:] in ('x86', 'x86_64', 'amd64', 'i386', 'i686'):
-                machine = '_x86' if not is_64bits else ''
-            # platform.machine() on 32-bit raspbian OS may return 'aarch64', so check "64-bitness"
-            # See: https://github.com/yt-dlp/yt-dlp/issues/11813
-            elif machine[1:] == 'aarch64' and not is_64bits:
-                machine = '_armv7l'
-            # sys.executable returns a /tmp/ path for staticx builds (linux_static)
-            # Ref: https://staticx.readthedocs.io/en/latest/usage.html#run-time-information
-            if static_exe_path := os.getenv('STATICX_PROG_PATH'):
-                path = static_exe_path
+            return f'darwin{machine}_exe', path
+
+        machine = f'_{platform.machine().lower()}'
+        is_64bits = sys.maxsize > 2**32
+        # Ref: https://en.wikipedia.org/wiki/Uname#Examples
+        if machine[1:] in ('x86', 'x86_64', 'amd64', 'i386', 'i686'):
+            machine = '_x86' if not is_64bits else ''
+        # platform.machine() on 32-bit raspbian OS may return 'aarch64', so check "64-bitness"
+        # See: https://github.com/yt-dlp/yt-dlp/issues/11813
+        elif machine[1:] == 'aarch64' and not is_64bits:
+            machine = '_armv7l'
+        # sys.executable returns a /tmp/ path for staticx builds (linux_static)
+        # Ref: https://staticx.readthedocs.io/en/latest/usage.html#run-time-information
+        if static_exe_path := os.getenv('STATICX_PROG_PATH'):
+            path = static_exe_path
+
         return f'{remove_end(sys.platform, "32")}{machine}_exe', path
 
     path = os.path.dirname(__file__)
@@ -111,7 +115,6 @@ def current_git_head():
     'win_exe': '.exe',
     'win_x86_exe': '_x86.exe',
     'darwin_exe': '_macos',
-    'darwin_legacy_exe': '_macos_legacy',
     'linux_exe': '_linux',
     'linux_aarch64_exe': '_linux_aarch64',
     'linux_armv7l_exe': '_linux_armv7l',
@@ -147,12 +150,6 @@ def _get_system_deprecation():
     STOP_MSG = 'You may stop receiving updates on this version at any time!'
     variant = detect_variant()
 
-    # Temporary until macos_legacy executable builds are discontinued
-    if variant == 'darwin_legacy_exe':
-        return EXE_MSG_TMPL.format(
-            f'{variant} (the PyInstaller-bundled executable for macOS versions older than 10.15)',
-            'issues/13856', STOP_MSG)
-
     # Temporary until linux_armv7l executable builds are discontinued
     if variant == 'linux_armv7l_exe':
         return EXE_MSG_TMPL.format(