diff --git a/.github/scripts/ci_loop_versions.py b/.github/scripts/ci_loop_versions.py
new file mode 100644
index 0000000..c65b14d
--- /dev/null
+++ b/.github/scripts/ci_loop_versions.py
@@ -0,0 +1,37 @@
+import argparse
+import json
+
+import requests
+from packaging.specifiers import SpecifierSet
+from packaging.version import Version
+
+
+def get_versions(package: str, version_spec: str) -> list[str]:
+    specifier = SpecifierSet(version_spec)
+
+    url = f"https://pypi.org/pypi/{package}/json"
+    resp = requests.get(url, timeout=30)
+    resp.raise_for_status()
+    data = resp.json()
+
+    all_versions = data["releases"].keys()
+
+    matched = sorted(
+        (Version(v) for v in all_versions if Version(v) in specifier),
+        reverse=True,
+    )
+    return [str(v) for v in matched]
+
+
+def main():
+    parser = argparse.ArgumentParser(description="List matching PyPI versions as JSON")
+    parser.add_argument("package", help="package name, e.g. setuptools")
+    parser.add_argument("version", help='version spec, e.g. ">=77.0.1,<83"')
+    args = parser.parse_args()
+
+    versions = get_versions(args.package, args.version)
+    print(json.dumps(versions))
+
+
+if __name__ == "__main__":
+    main()
diff --git a/.github/workflows/compatibility.yml b/.github/workflows/compatibility.yml
new file mode 100644
index 0000000..20f4fc1
--- /dev/null
+++ b/.github/workflows/compatibility.yml
@@ -0,0 +1,69 @@
+name: Test Compatibility
+
+on:
+  push:
+    paths:
+      - pyproject.toml
+  workflow_dispatch:
+
+permissions:
+  contents: read
+
+jobs:
+  prepare:
+    runs-on: ubuntu-latest
+    outputs:
+      versions: ${{ steps.parser.outputs.versions || '[]' }}
+    steps:
+      - uses: actions/checkout@v6
+        with:
+          fetch-depth: 2
+
+      - name: Check license line changed
+        id: check
+        run: |
+          if [ "${{ github.event_name }}" = "workflow_dispatch" ]; then
+            echo "changed=true" >> "$GITHUB_OUTPUT"
+          elif git diff HEAD~1 HEAD -- pyproject.toml | grep -q '^[+-].*license = "Apache-2.0"'; then
+            echo "changed=true" >> "$GITHUB_OUTPUT"
+          else
+            echo "changed=false" >> "$GITHUB_OUTPUT"
+          fi
+
+      - uses: actions/setup-python@v6
+        if: steps.check.outputs.changed == 'true'
+        with:
+          python-version: "3.14"
+
+      - name: Generate version matrix
+        if: steps.check.outputs.changed == 'true'
+        id: parser
+        run: |
+          versions=$(python ci_loop_versions.py setuptools ">=77.0.1,<83")
+          echo "versions=$versions" >> "$GITHUB_OUTPUT"
+
+  check:
+    needs: prepare
+    if: needs.prepare.outputs.versions != '[]'
+    runs-on: ubuntu-latest
+    strategy:
+      fail-fast: false
+      matrix:
+        version: ${{ fromJSON(needs.prepare.outputs.versions) }}
+
+    steps:
+      - uses: actions/checkout@v6
+      - uses: actions/setup-python@v6
+        with:
+          python-version: "3.14"
+          cache: pip
+
+      - name: Install package with selected setuptools
+        run: |
+          python -m pip install --upgrade pip
+          python -m pip install . "setuptools==${{ matrix.version }}"
+
+      - name: Show versions
+        run: |
+          python --version
+          python -m pip show setuptools
diff --git a/pyproject.toml b/pyproject.toml
index da5fdc7..2b171af 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -16,7 +16,7 @@
 
 
 [build-system]
-requires = ["setuptools>=61"]
+requires = ["setuptools>=77.0.1,<83"]
 build-backend = "setuptools.build_meta"
 
 [project]