diff --git a/bin/update_virtualenv.py b/bin/update_virtualenv.py
index a18c5f7db..fc69cf63d 100755
--- a/bin/update_virtualenv.py
+++ b/bin/update_virtualenv.py
@@ -53,10 +53,6 @@ def git_ls_remote_versions(url) -> list[VersionTuple]:
             if version.is_prerelease:
                 log.info("Ignoring pre-release %r", str(version))
                 continue
-            # Do not upgrade past 20.22.0 to keep python 3.6 compat
-            if version >= Version("20.22.0"):
-                log.info("Ignoring %r which is not compatible with python 3.6", str(version))
-                continue
             versions.append(VersionTuple(version, version_string))
         except InvalidVersion:
             log.warning("Ignoring ref %r", ref)
@@ -82,15 +78,20 @@ def update_virtualenv(force: bool, level: str) -> None:
 
     original_toml = toml_file_path.read_text()
     with toml_file_path.open("rb") as f:
-        loaded_file = tomllib.load(f)
-    version = str(loaded_file["version"])
+        configurations = tomllib.load(f)
+    default = configurations.pop("default")
+    version = str(default["version"])
     versions = git_ls_remote_versions(GET_VIRTUALENV_GITHUB)
     if versions[0].version > Version(version):
         version = versions[0].version_string
 
-    result_toml = (
-        f'version = "{version}"\n'
-        f'url = "{GET_VIRTUALENV_URL_TEMPLATE.format(version=version)}"\n'
+    configurations["default"] = {
+        "version": version,
+        "url": GET_VIRTUALENV_URL_TEMPLATE.format(version=version),
+    }
+    result_toml = "".join(
+        f'{key} = {{ version = "{value["version"]}", url = "{value["url"]}" }}\n'
+        for key, value in configurations.items()
     )
 
     rich.print()  # spacer
diff --git a/cibuildwheel/macos.py b/cibuildwheel/macos.py
index 44f9ecf0e..6b219a102 100644
--- a/cibuildwheel/macos.py
+++ b/cibuildwheel/macos.py
@@ -181,7 +181,9 @@ def setup_python(
 
     log.step("Setting up build environment...")
     venv_path = tmp / "venv"
-    env = virtualenv(base_python, venv_path, dependency_constraint_flags)
+    env = virtualenv(
+        python_configuration.version, base_python, venv_path, dependency_constraint_flags
+    )
     venv_bin_path = venv_path / "bin"
     assert venv_bin_path.exists()
     # Fix issue with site.py setting the wrong `sys.prefix`, `sys.exec_prefix`,
diff --git a/cibuildwheel/resources/virtualenv.toml b/cibuildwheel/resources/virtualenv.toml
index 446d0540e..8d89dc106 100644
--- a/cibuildwheel/resources/virtualenv.toml
+++ b/cibuildwheel/resources/virtualenv.toml
@@ -1,2 +1,2 @@
-version = "20.21.1"
-url = "https://github.com/pypa/get-virtualenv/blob/20.21.1/public/virtualenv.pyz?raw=true"
+py36 = { version = "20.21.1", url = "https://github.com/pypa/get-virtualenv/blob/20.21.1/public/virtualenv.pyz?raw=true" }
+default = { version = "20.26.2", url = "https://github.com/pypa/get-virtualenv/blob/20.26.2/public/virtualenv.pyz?raw=true" }
diff --git a/cibuildwheel/util.py b/cibuildwheel/util.py
index 410b1c02a..66be99ca7 100644
--- a/cibuildwheel/util.py
+++ b/cibuildwheel/util.py
@@ -526,12 +526,15 @@ def get_pip_version(env: Mapping[str, str]) -> str:
 
 
 @lru_cache(maxsize=None)
-def _ensure_virtualenv() -> Path:
+def _ensure_virtualenv(version: str) -> Path:
+    version_parts = version.split(".")
+    key = f"py{version_parts[0]}{version_parts[1]}"
     input_file = resources_dir / "virtualenv.toml"
     with input_file.open("rb") as f:
         loaded_file = tomllib.load(f)
-    version = str(loaded_file["version"])
-    url = str(loaded_file["url"])
+    configuration = loaded_file.get(key, loaded_file["default"])
+    version = str(configuration["version"])
+    url = str(configuration["url"])
     path = CIBW_CACHE_PATH / f"virtualenv-{version}.pyz"
     with FileLock(str(path) + ".lock"):
         if not path.exists():
@@ -587,10 +590,10 @@ def _parse_constraints_for_virtualenv(
 
 
 def virtualenv(
-    python: Path, venv_path: Path, dependency_constraint_flags: Sequence[PathOrStr]
+    version: str, python: Path, venv_path: Path, dependency_constraint_flags: Sequence[PathOrStr]
 ) -> dict[str, str]:
     assert python.exists()
-    virtualenv_app = _ensure_virtualenv()
+    virtualenv_app = _ensure_virtualenv(version)
     allowed_seed_packages = ["pip", "setuptools", "wheel"]
     constraints = _parse_constraints_for_virtualenv(
         allowed_seed_packages, dependency_constraint_flags
diff --git a/cibuildwheel/windows.py b/cibuildwheel/windows.py
index 13d3a1857..e661716d4 100644
--- a/cibuildwheel/windows.py
+++ b/cibuildwheel/windows.py
@@ -246,7 +246,9 @@ def setup_python(
 
     log.step("Setting up build environment...")
     venv_path = tmp / "venv"
-    env = virtualenv(base_python, venv_path, dependency_constraint_flags)
+    env = virtualenv(
+        python_configuration.version, base_python, venv_path, dependency_constraint_flags
+    )
 
     # set up environment variables for run_with_env
     env["PYTHON_VERSION"] = python_configuration.version
diff --git a/test/test_dependency_versions.py b/test/test_dependency_versions.py
index 760675d74..17edd10f3 100644
--- a/test/test_dependency_versions.py
+++ b/test/test_dependency_versions.py
@@ -111,7 +111,6 @@ def test_dependency_constraints_file(tmp_path, build_frontend_env):
             """
             pip=={pip}
             delocate=={delocate}
-            importlib-metadata<3,>=0.12; python_version < "3.8"
             """.format(**tool_versions)
         )
     )