diff --git a/.github/workflows/tail-call.yml b/.github/workflows/tail-call.yml
index a47e532d396bc0..1cfc78d6eedbbe 100644
--- a/.github/workflows/tail-call.yml
+++ b/.github/workflows/tail-call.yml
@@ -1,19 +1,14 @@
 name: Tail calling interpreter
 on:
   pull_request:
-    paths:
+    paths: &paths
       - '.github/workflows/tail-call.yml'
       - 'Python/bytecodes.c'
       - 'Python/ceval.c'
       - 'Python/ceval_macros.h'
       - 'Python/generated_cases.c.h'
   push:
-    paths:
-      - '.github/workflows/tail-call.yml'
-      - 'Python/bytecodes.c'
-      - 'Python/ceval.c'
-      - 'Python/ceval_macros.h'
-      - 'Python/generated_cases.c.h'
+    paths: *paths
   workflow_dispatch:
 
 permissions:
@@ -25,6 +20,7 @@ concurrency:
 
 env:
   FORCE_COLOR: 1
+  LLVM_VERSION: 21
 
 jobs:
   tail-call:
@@ -34,32 +30,17 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        target:
-# Un-comment as we add support for more platforms for tail-calling interpreters.
-#          - i686-pc-windows-msvc/msvc
-          - x86_64-pc-windows-msvc/msvc
-          - free-threading-msvc
-#          - aarch64-pc-windows-msvc/msvc
-          - x86_64-apple-darwin/clang
-          - aarch64-apple-darwin/clang
-          - x86_64-unknown-linux-gnu/gcc
-          - aarch64-unknown-linux-gnu/gcc
-          - free-threading
-        llvm:
-          - 20
         include:
-#          - target: i686-pc-windows-msvc/msvc
-#            architecture: Win32
-#            runner: windows-2022
           - target: x86_64-pc-windows-msvc/msvc
             architecture: x64
             runner: windows-2025-vs2026
-          - target: free-threading-msvc
+            build_flags: ""
+            run_tests: true
+          - target: x86_64-pc-windows-msvc/msvc-free-threading
             architecture: x64
             runner: windows-2025-vs2026
-#          - target: aarch64-pc-windows-msvc/msvc
-#            architecture: ARM64
-#            runner: windows-2022
+            build_flags: --disable-gil
+            run_tests: false
           - target: x86_64-apple-darwin/clang
             architecture: x86_64
             runner: macos-15-intel
@@ -69,12 +50,15 @@ jobs:
           - target: x86_64-unknown-linux-gnu/gcc
             architecture: x86_64
             runner: ubuntu-24.04
+            configure_flags: --with-pydebug
+          - target: x86_64-unknown-linux-gnu/gcc-free-threading
+            architecture: x86_64
+            runner: ubuntu-24.04
+            configure_flags: --disable-gil
           - target: aarch64-unknown-linux-gnu/gcc
             architecture: aarch64
             runner: ubuntu-24.04-arm
-          - target: free-threading
-            architecture: x86_64
-            runner: ubuntu-24.04
+            configure_flags: --with-pydebug
     steps:
       - uses: actions/checkout@v6
         with:
@@ -84,58 +68,32 @@ jobs:
           python-version: '3.11'
 
       - name: Native Windows MSVC (release)
-        if: runner.os == 'Windows' && matrix.architecture != 'ARM64' && matrix.target != 'free-threading-msvc'
-        shell: pwsh
-        run: |
-          $env:PlatformToolset = "v145"
-          ./PCbuild/build.bat --tail-call-interp -c Release -p ${{ matrix.architecture }}
-          ./PCbuild/rt.bat -p ${{ matrix.architecture }} -q --multiprocess 0 --timeout 4500 --verbose2 --verbose3
-
-        # No tests:
-      - name: Native Windows MSVC with free-threading (release)
-        if: matrix.target == 'free-threading-msvc'
+        if: runner.os == 'Windows'
         shell: pwsh
         run: |
           $env:PlatformToolset = "v145"
-          ./PCbuild/build.bat --tail-call-interp --disable-gil -c Release -p ${{ matrix.architecture }}
-
-      # No tests (yet):
-      - name: Emulated Windows Clang (release)
-        if: runner.os == 'Windows' && matrix.architecture == 'ARM64'
-        shell: pwsh
-        run: |
-          choco install llvm --allow-downgrade --no-progress --version ${{ matrix.llvm }}.1.0
-          $env:PlatformToolset = "clangcl"
-          $env:LLVMToolsVersion = "${{ matrix.llvm }}.1.0"
-          $env:LLVMInstallDir = "C:\Program Files\LLVM"
-          ./PCbuild/build.bat --tail-call-interp -p ${{ matrix.architecture }}
+          ./PCbuild/build.bat --tail-call-interp ${{ matrix.build_flags }} -c Release -p ${{ matrix.architecture }}
+          if ("${{ matrix.run_tests }}" -eq "true") {
+            ./PCbuild/rt.bat -p ${{ matrix.architecture }} -q --multiprocess 0 --timeout 4500 --verbose2 --verbose3
+          }
 
       - name: Native macOS (release)
         if: runner.os == 'macOS'
         run: |
           brew update
-          brew install llvm@${{ matrix.llvm }}
+          brew install llvm@${{ env.LLVM_VERSION }}
           export SDKROOT="$(xcrun --show-sdk-path)"
-          export PATH="/usr/local/opt/llvm@${{ matrix.llvm }}/bin:$PATH"
-          export PATH="/opt/homebrew/opt/llvm@${{ matrix.llvm }}/bin:$PATH"
-          CC=clang-20 ./configure --with-tail-call-interp
+          export PATH="/usr/local/opt/llvm@${{ env.LLVM_VERSION }}/bin:$PATH"
+          export PATH="/opt/homebrew/opt/llvm@${{ env.LLVM_VERSION }}/bin:$PATH"
+          CC=clang-${{ env.LLVM_VERSION }} ./configure --with-tail-call-interp
           make all --jobs 4
           ./python.exe -m test --multiprocess 0 --timeout 4500 --verbose2 --verbose3
 
-      - name: Native Linux (debug)
-        if: runner.os == 'Linux' && matrix.target != 'free-threading'
-        run: |
-          sudo bash -c "$(wget -O - https://apt.llvm.org/llvm.sh)" ./llvm.sh ${{ matrix.llvm }}
-          export PATH="$(llvm-config-${{ matrix.llvm }} --bindir):$PATH"
-          CC=clang-20 ./configure --with-tail-call-interp --with-pydebug
-          make all --jobs 4
-          ./python -m test --multiprocess 0 --timeout 4500 --verbose2 --verbose3
-
-      - name: Native Linux with free-threading (release)
-        if: matrix.target == 'free-threading'
+      - name: Native Linux
+        if: runner.os == 'Linux'
         run: |
-          sudo bash -c "$(wget -O - https://apt.llvm.org/llvm.sh)" ./llvm.sh ${{ matrix.llvm }}
-          export PATH="$(llvm-config-${{ matrix.llvm }} --bindir):$PATH"
-          CC=clang-20 ./configure --with-tail-call-interp --disable-gil
+          sudo bash -c "$(wget -O - https://apt.llvm.org/llvm.sh)" ./llvm.sh ${{ env.LLVM_VERSION }}
+          export PATH="$(llvm-config-${{ env.LLVM_VERSION }} --bindir):$PATH"
+          CC=clang-${{ env.LLVM_VERSION }} ./configure --with-tail-call-interp ${{ matrix.configure_flags }}
           make all --jobs 4
           ./python -m test --multiprocess 0 --timeout 4500 --verbose2 --verbose3