diff --git a/cibuildwheel/macos.py b/cibuildwheel/macos.py
index 65551668..bf25bb59 100644
--- a/cibuildwheel/macos.py
+++ b/cibuildwheel/macos.py
@@ -33,6 +33,7 @@ def get_macos_version() -> Tuple[int, int]:
 
     These tuples can be used in comparisons, e.g.
         (10, 14) <= (11, 0) == True
+        (10, 14) <= (10, 16) == True
         (11, 2) <= (11, 0) != True
     '''
     version_str, _, _ = platform.mac_ver()
@@ -71,7 +72,9 @@ def get_python_configurations(build_selector: BuildSelector,
     # skip builds as required by BUILD/SKIP
     python_configurations = [c for c in python_configurations if build_selector(c.identifier)]
 
-    if get_macos_version() >= (11, 0):
+    # When running on macOS 11 in x86_64 mode, the reported OS is the
+    # non-existent '10.16'.
+    if get_macos_version() >= (10, 16):
         if any(c.identifier.startswith('pp') for c in python_configurations):
             # pypy doesn't work on macOS 11 yet
             # See https://foss.heptapod.net/pypy/pypy/-/issues/3314
diff --git a/test/test_macos_archs.py b/test/test_macos_archs.py
index 2fd21535..5cec82c2 100644
--- a/test/test_macos_archs.py
+++ b/test/test_macos_archs.py
@@ -14,7 +14,7 @@ ALL_MACOS_WHEELS = (
 def test_cross_compiled_build(tmp_path):
     if utils.platform != 'macos':
         pytest.skip('this test is only relevant to macos')
-    if utils.get_macos_version() < (11, 0):
+    if utils.get_macos_version() < (10, 16):
         pytest.skip('this test only works on macOS 11 or greater')
 
     project_dir = tmp_path / 'project'
@@ -33,7 +33,7 @@ def test_cross_compiled_build(tmp_path):
 def test_cross_compiled_test(tmp_path, capfd, build_universal2):
     if utils.platform != 'macos':
         pytest.skip('this test is only relevant to macos')
-    if utils.get_macos_version() < (11, 0):
+    if utils.get_macos_version() < (10, 16):
         pytest.skip('this test only works on macOS 11 or greater')
 
     project_dir = tmp_path / 'project'