diff --git a/newsfragments/+61911d95.bugfix.rst b/newsfragments/+61911d95.bugfix.rst
new file mode 100644
index 0000000000..f542998cd5
--- /dev/null
+++ b/newsfragments/+61911d95.bugfix.rst
@@ -0,0 +1 @@
+Synced with pypa/distutils@30b7331 including fix for modified check on empty sources (pypa/distutils#284).
\ No newline at end of file
diff --git a/setuptools/_distutils/_modified.py b/setuptools/_distutils/_modified.py
index 6532aa1073..b7bdaa2943 100644
--- a/setuptools/_distutils/_modified.py
+++ b/setuptools/_distutils/_modified.py
@@ -63,7 +63,7 @@ def missing_as_newer(source):
         return missing == 'newer' and not os.path.exists(source)
 
     ignored = os.path.exists if missing == 'ignore' else None
-    return any(
+    return not os.path.exists(target) or any(
         missing_as_newer(source) or _newer(source, target)
         for source in filter(ignored, sources)
     )
diff --git a/setuptools/_distutils/dist.py b/setuptools/_distutils/dist.py
index 0a57d60be9..115302b3e7 100644
--- a/setuptools/_distutils/dist.py
+++ b/setuptools/_distutils/dist.py
@@ -658,7 +658,7 @@ def _show_help(
             )
             print()
 
-        for command in self.commands:
+        for command in commands:
             if isinstance(command, type) and issubclass(command, Command):
                 klass = command
             else:
diff --git a/setuptools/_distutils/tests/test_modified.py b/setuptools/_distutils/tests/test_modified.py
index 2bd82346cf..e35cec2d6f 100644
--- a/setuptools/_distutils/tests/test_modified.py
+++ b/setuptools/_distutils/tests/test_modified.py
@@ -117,3 +117,10 @@ def test_newer_pairwise_group(groups_target):
     newer = newer_pairwise_group([groups_target.newer], [groups_target.target])
     assert older == ([], [])
     assert newer == ([groups_target.newer], [groups_target.target])
+
+
+def test_newer_group_no_sources_no_target(tmp_path):
+    """
+    Consider no sources and no target "newer".
+    """
+    assert newer_group([], str(tmp_path / 'does-not-exist'))