diff --git a/.github/workflows/tail-call.yml b/.github/workflows/tail-call.yml
index 4c2516c517b3a9..8e7dc2b4552922 100644
--- a/.github/workflows/tail-call.yml
+++ b/.github/workflows/tail-call.yml
@@ -65,6 +65,10 @@ jobs:
           - target: aarch64-unknown-linux-gnu/gcc
             architecture: aarch64
             runner: ubuntu-22.04-arm
+          - target: x86_64-unknown-linux-gnu/gcc
+            architecture: x86_64
+            runner: ubuntu-24.04
+            free-threading: true
     steps:
       - uses: actions/checkout@v4
         with:
@@ -113,3 +117,12 @@ jobs:
           make all --jobs 4
           ./python -m test --multiprocess 0 --timeout 4500 --verbose2 --verbose3
 
+      - name: Native Linux with free-threading (release)
+        if: runner.os == 'Linux' && matrix.free-threading == 'true'
+        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-19 ./configure --with-tail-call-interp --disable-gil
+          make all --jobs 4
+          ./python -m test --multiprocess 0 --timeout 4500 --verbose2 --verbose3
+
diff --git a/Tools/requirements-dev.txt b/Tools/requirements-dev.txt
index e5badaccadda40..571102f02ce2fc 100644
--- a/Tools/requirements-dev.txt
+++ b/Tools/requirements-dev.txt
@@ -4,4 +4,4 @@ mypy==1.13
 
 # needed for peg_generator:
 types-psutil==6.0.0.20240901
-types-setuptools==74.0.0.20240831
+types-setuptools==75.8.0.20250210