diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index a33e347996342a..bf94f264215063 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -62,8 +62,6 @@ jobs:
         with:
           fetch-depth: 1
           persist-credentials: false
-      - name: Runner image version
-        run: echo "IMAGE_VERSION=${ImageVersion}" >> "$GITHUB_ENV"
       - name: Check Autoconf and aclocal versions
         run: |
           grep "Generated by GNU Autoconf 2.72" configure
@@ -104,14 +102,14 @@ jobs:
         with:
           python-version: '3.x'
       - name: Runner image version
-        run: echo "IMAGE_VERSION=${ImageVersion}" >> "$GITHUB_ENV"
+        run: echo "IMAGE_OS_VERSION=${ImageOS}-${ImageVersion}" >> "$GITHUB_ENV"
       - name: Restore config.cache
         uses: actions/cache@v4
         with:
           path: config.cache
           # Include env.pythonLocation in key to avoid changes in environment when setup-python updates Python
-          key: ${{ github.job }}-${{ runner.os }}-${{ env.IMAGE_VERSION }}-${{ needs.build-context.outputs.config-hash }}-${{ env.pythonLocation }}
-      - name: Install Dependencies
+          key: ${{ github.job }}-${{ env.IMAGE_OS_VERSION }}-${{ needs.build-context.outputs.config-hash }}-${{ env.pythonLocation }}
+      - name: Install dependencies
         run: sudo ./.github/workflows/posix-deps-apt.sh
       - name: Add ccache to PATH
         run: echo "PATH=/usr/lib/ccache:$PATH" >> "$GITHUB_ENV"
@@ -284,15 +282,15 @@ jobs:
       with:
         persist-credentials: false
     - name: Runner image version
-      run: echo "IMAGE_VERSION=${ImageVersion}" >> "$GITHUB_ENV"
+      run: echo "IMAGE_OS_VERSION=${ImageOS}-${ImageVersion}" >> "$GITHUB_ENV"
     - name: Restore config.cache
       uses: actions/cache@v4
       with:
         path: config.cache
-        key: ${{ github.job }}-${{ runner.os }}-${{ env.IMAGE_VERSION }}-${{ needs.build-context.outputs.config-hash }}
+        key: ${{ github.job }}-${{ env.IMAGE_OS_VERSION }}-${{ needs.build-context.outputs.config-hash }}
     - name: Register gcc problem matcher
       run: echo "::add-matcher::.github/problem-matchers/gcc.json"
-    - name: Install Dependencies
+    - name: Install dependencies
       run: sudo ./.github/workflows/posix-deps-apt.sh
     - name: Configure OpenSSL env vars
       run: |
@@ -347,7 +345,7 @@ jobs:
         persist-credentials: false
     - name: Register gcc problem matcher
       run: echo "::add-matcher::.github/problem-matchers/gcc.json"
-    - name: Install Dependencies
+    - name: Install dependencies
       run: sudo ./.github/workflows/posix-deps-apt.sh
     - name: Configure OpenSSL env vars
       run: |
@@ -379,12 +377,12 @@ jobs:
     - name: Bind mount sources read-only
       run: sudo mount --bind -o ro "$GITHUB_WORKSPACE" "$CPYTHON_RO_SRCDIR"
     - name: Runner image version
-      run: echo "IMAGE_VERSION=${ImageVersion}" >> "$GITHUB_ENV"
+      run: echo "IMAGE_OS_VERSION=${ImageOS}-${ImageVersion}" >> "$GITHUB_ENV"
     - name: Restore config.cache
       uses: actions/cache@v4
       with:
         path: ${{ env.CPYTHON_BUILDDIR }}/config.cache
-        key: ${{ github.job }}-${{ runner.os }}-${{ env.IMAGE_VERSION }}-${{ needs.build-context.outputs.config-hash }}
+        key: ${{ github.job }}-${{ env.IMAGE_OS_VERSION }}-${{ needs.build-context.outputs.config-hash }}
     - name: Configure CPython out-of-tree
       working-directory: ${{ env.CPYTHON_BUILDDIR }}
       run: |
@@ -466,15 +464,15 @@ jobs:
       with:
         persist-credentials: false
     - name: Runner image version
-      run: echo "IMAGE_VERSION=${ImageVersion}" >> "$GITHUB_ENV"
+      run: echo "IMAGE_OS_VERSION=${ImageOS}-${ImageVersion}" >> "$GITHUB_ENV"
     - name: Restore config.cache
       uses: actions/cache@v4
       with:
         path: config.cache
-        key: ${{ github.job }}-${{ runner.os }}-${{ env.IMAGE_VERSION }}-${{ needs.build-context.outputs.config-hash }}
+        key: ${{ github.job }}-${{ env.IMAGE_OS_VERSION }}-${{ needs.build-context.outputs.config-hash }}
     - name: Register gcc problem matcher
       run: echo "::add-matcher::.github/problem-matchers/gcc.json"
-    - name: Install Dependencies
+    - name: Install dependencies
       run: sudo ./.github/workflows/posix-deps-apt.sh
     - name: Set up GCC-10 for ASAN
       uses: egor-tensin/setup-gcc@v1
@@ -537,19 +535,19 @@ jobs:
         with:
           persist-credentials: false
       - name: Runner image version
-        run: echo "IMAGE_VERSION=${ImageVersion}" >> "$GITHUB_ENV"
+        run: echo "IMAGE_OS_VERSION=${ImageOS}-${ImageVersion}" >> "$GITHUB_ENV"
       - name: Restore config.cache
         uses: actions/cache@v4
         with:
           path: config.cache
-          key: ${{ github.job }}-${{ runner.os }}-${{ env.IMAGE_VERSION }}-${{ needs.build-context.outputs.config-hash }}
+          key: ${{ github.job }}-${{ env.IMAGE_OS_VERSION }}-${{ needs.build-context.outputs.config-hash }}
       - name: Register gcc problem matcher
         run: echo "::add-matcher::.github/problem-matchers/gcc.json"
       - name: Set build dir
         run:
           # an absolute path outside of the working directoy
           echo "BUILD_DIR=$(realpath ${{ github.workspace }}/../build)" >> "$GITHUB_ENV"
-      - name: Install Dependencies
+      - name: Install dependencies
         run: sudo ./.github/workflows/posix-deps-apt.sh
       - name: Configure host build
         run: ./configure --prefix="$BUILD_DIR/host-python"
diff --git a/.github/workflows/reusable-macos.yml b/.github/workflows/reusable-macos.yml
index 4e7aced94a321c..43ce0f957d2d49 100644
--- a/.github/workflows/reusable-macos.yml
+++ b/.github/workflows/reusable-macos.yml
@@ -35,12 +35,12 @@ jobs:
       with:
         persist-credentials: false
     - name: Runner image version
-      run: echo "IMAGE_VERSION=${ImageVersion}" >> "$GITHUB_ENV"
+      run: echo "IMAGE_OS_VERSION=${ImageOS}-${ImageVersion}" >> "$GITHUB_ENV"
     - name: Restore config.cache
       uses: actions/cache@v4
       with:
         path: config.cache
-        key: ${{ github.job }}-${{ inputs.os }}-${{ env.IMAGE_VERSION }}-${{ inputs.config_hash }}
+        key: ${{ github.job }}-${{ env.IMAGE_OS_VERSION }}-${{ inputs.config_hash }}
     - name: Install Homebrew dependencies
       run: |
         brew install pkg-config openssl@3.0 xz gdbm tcl-tk@8 make
diff --git a/.github/workflows/reusable-tsan.yml b/.github/workflows/reusable-tsan.yml
index 8ac2f84099e563..5c815f72f0ada5 100644
--- a/.github/workflows/reusable-tsan.yml
+++ b/.github/workflows/reusable-tsan.yml
@@ -25,13 +25,13 @@ jobs:
       with:
         persist-credentials: false
     - name: Runner image version
-      run: echo "IMAGE_VERSION=${ImageVersion}" >> "$GITHUB_ENV"
+      run: echo "IMAGE_OS_VERSION=${ImageOS}-${ImageVersion}" >> "$GITHUB_ENV"
     - name: Restore config.cache
       uses: actions/cache@v4
       with:
         path: config.cache
-        key: ${{ github.job }}-${{ runner.os }}-${{ env.IMAGE_VERSION }}-${{ inputs.config_hash }}
-    - name: Install Dependencies
+        key: ${{ github.job }}-${{ env.IMAGE_OS_VERSION }}-${{ inputs.config_hash }}
+    - name: Install dependencies
       run: |
         sudo ./.github/workflows/posix-deps-apt.sh
         # Install clang-18
@@ -44,7 +44,7 @@ jobs:
         sudo update-alternatives --set clang++ /usr/bin/clang++-17
         # Reduce ASLR to avoid TSAN crashing
         sudo sysctl -w vm.mmap_rnd_bits=28
-    - name: TSAN Option Setup
+    - name: TSAN option setup
       run: |
         echo "TSAN_OPTIONS=log_path=${GITHUB_WORKSPACE}/tsan_log suppressions=${GITHUB_WORKSPACE}/Tools/tsan/suppressions${{
             fromJSON(inputs.free-threading)
diff --git a/.github/workflows/reusable-ubuntu.yml b/.github/workflows/reusable-ubuntu.yml
index aa8ba00f19d8ca..9b366d4dfc212d 100644
--- a/.github/workflows/reusable-ubuntu.yml
+++ b/.github/workflows/reusable-ubuntu.yml
@@ -78,12 +78,12 @@ jobs:
     - name: Bind mount sources read-only
       run: sudo mount --bind -o ro "$GITHUB_WORKSPACE" "$CPYTHON_RO_SRCDIR"
     - name: Runner image version
-      run: echo "IMAGE_VERSION=${ImageVersion}" >> "$GITHUB_ENV"
+      run: echo "IMAGE_OS_VERSION=${ImageOS}-${ImageVersion}" >> "$GITHUB_ENV"
     - name: Restore config.cache
       uses: actions/cache@v4
       with:
         path: ${{ env.CPYTHON_BUILDDIR }}/config.cache
-        key: ${{ github.job }}-${{ runner.os }}-${{ env.IMAGE_VERSION }}-${{ inputs.config_hash }}
+        key: ${{ github.job }}-${{ env.IMAGE_OS_VERSION }}-${{ inputs.config_hash }}
     - name: Configure CPython out-of-tree
       working-directory: ${{ env.CPYTHON_BUILDDIR }}
       # `test_unpickle_module_race` writes to the source directory, which is
diff --git a/.github/workflows/reusable-wasi.yml b/.github/workflows/reusable-wasi.yml
index 4456b83c8e0032..36a0e4ef673260 100644
--- a/.github/workflows/reusable-wasi.yml
+++ b/.github/workflows/reusable-wasi.yml
@@ -53,6 +53,8 @@ jobs:
       uses: actions/setup-python@v5
       with:
         python-version: '3.x'
+    - name: "Runner image version"
+      run: echo "IMAGE_OS_VERSION=${ImageOS}-${ImageVersion}" >> "$GITHUB_ENV"
     - name: "Restore Python build config.cache"
       uses: actions/cache@v4
       with:
@@ -60,7 +62,7 @@ jobs:
         # Include env.pythonLocation in key to avoid changes in environment when setup-python updates Python.
         # Include the hash of `Tools/wasm/wasi.py` as it may change the environment variables.
         # (Make sure to keep the key in sync with the other config.cache step below.)
-        key: ${{ github.job }}-${{ runner.os }}-${{ env.IMAGE_VERSION }}-${{ env.WASI_SDK_VERSION }}-${{ env.WASMTIME_VERSION }}-${{ inputs.config_hash }}-${{ hashFiles('Tools/wasm/wasi.py') }}-${{ env.pythonLocation }}
+        key: ${{ github.job }}-${{ env.IMAGE_OS_VERSION }}-${{ env.WASI_SDK_VERSION }}-${{ env.WASMTIME_VERSION }}-${{ inputs.config_hash }}-${{ hashFiles('Tools/wasm/wasi.py') }}-${{ env.pythonLocation }}
     - name: "Configure build Python"
       run: python3 Tools/wasm/wasi.py configure-build-python -- --config-cache --with-pydebug
     - name: "Make build Python"
@@ -70,7 +72,7 @@ jobs:
       with:
         path: ${{ env.CROSS_BUILD_WASI }}/config.cache
         # Should be kept in sync with the other config.cache step above.
-        key: ${{ github.job }}-${{ runner.os }}-${{ env.IMAGE_VERSION }}-${{ env.WASI_SDK_VERSION }}-${{ env.WASMTIME_VERSION }}-${{ inputs.config_hash }}-${{ hashFiles('Tools/wasm/wasi.py') }}-${{ env.pythonLocation }}
+        key: ${{ github.job }}-${{ env.IMAGE_OS_VERSION }}-${{ env.WASI_SDK_VERSION }}-${{ env.WASMTIME_VERSION }}-${{ inputs.config_hash }}-${{ hashFiles('Tools/wasm/wasi.py') }}-${{ env.pythonLocation }}
     - name: "Configure host"
       # `--with-pydebug` inferred from configure-build-python
       run: python3 Tools/wasm/wasi.py configure-host -- --config-cache