diff --git a/Lib/test/test_subprocess.py b/Lib/test/test_subprocess.py
--- a/Lib/test/test_subprocess.py
+++ b/Lib/test/test_subprocess.py
@@ -191,9 +191,52 @@
         p.wait()
         self.assertEqual(p.stderr, None)
 
+    def test_cwd(self):
+        tmpdir = tempfile.gettempdir()
+        # We cannot use os.path.realpath to canonicalize the path,
+        # since it doesn't expand Tru64 {memb} strings. See bug 1063571.
+        cwd = os.getcwd()
+        os.chdir(tmpdir)
+        tmpdir = os.getcwd()
+        os.chdir(cwd)
+        p = subprocess.Popen([sys.executable, "-c",
+                              'import sys,os;'
+                              'sys.stdout.write(os.getcwd())'],
+                             stdout=subprocess.PIPE,
+                             cwd=tmpdir)
+        self.addCleanup(p.stdout.close)
+        normcase = os.path.normcase
+        self.assertEqual(normcase(p.stdout.read().decode("utf-8")),
+                         normcase(tmpdir))
+
     @unittest.skipIf(sys.base_prefix != sys.prefix,
                      'Test is not venv-compatible')
-    def test_executable_with_cwd(self):
+    def test_cwd_wrong(self):
+        # Check that Popen looks for args[0] relative to cwd (failing case).
+        python_path = os.path.realpath(sys.executable)
+        python_dir, python_base = os.path.split(python_path)
+        wrong_cwd = os.path.join(python_dir, 'Doc')
+        self.assertRaises(FileNotFoundError, subprocess.Popen,
+                          [python_base], cwd=wrong_cwd)
+
+    @unittest.skipIf(sys.base_prefix != sys.prefix,
+                     'Test is not venv-compatible')
+    def test_cwd_with_relative_arg(self):
+        # Check that Popen looks for args[0] relative to cwd (succeeding case).
+        python_path = os.path.realpath(sys.executable)
+        python_dir, python_base = os.path.split(python_path)
+        wrong_cwd = os.path.join(python_dir, 'Doc')
+        relative_python = os.path.join(os.pardir, python_base)
+        p = subprocess.Popen([relative_python, "-c",
+                              "import sys; sys.exit(47)"], cwd=wrong_cwd)
+        p.wait()
+        self.assertEqual(p.returncode, 47)
+
+    @unittest.skipIf(sys.base_prefix != sys.prefix,
+                     'Test is not venv-compatible')
+    def test_cwd_with_absolute_executable(self):
+        # Check that an absolute path for executable works with cwd (and that
+        # executable takes precedence over args[0]).
         python_dir = os.path.dirname(os.path.realpath(sys.executable))
         p = subprocess.Popen(["somethingyoudonthave", "-c",
                               "import sys; sys.exit(47)"],
@@ -203,6 +246,21 @@
 
     @unittest.skipIf(sys.base_prefix != sys.prefix,
                      'Test is not venv-compatible')
+    def test_cwd_with_relative_executable(self):
+        # Check that Popen looks for executable relative to cwd (and that
+        # executable takes precedence over args[0]).
+        python_path = os.path.realpath(sys.executable)
+        python_dir, python_base = os.path.split(python_path)
+        wrong_cwd = os.path.join(python_dir, 'Doc')
+        relative_python = os.path.join(os.pardir, python_base)
+        p = subprocess.Popen(["somethingyoudonthave", "-c",
+                              "import sys; sys.exit(47)"],
+                             executable=relative_python, cwd=wrong_cwd)
+        p.wait()
+        self.assertEqual(p.returncode, 47)
+
+    @unittest.skipIf(sys.base_prefix != sys.prefix,
+                     'Test is not venv-compatible')
     @unittest.skipIf(sysconfig.is_python_build(),
                      "need an installed Python. See #7774")
     def test_executable_without_cwd(self):
@@ -369,24 +427,6 @@
         p.wait()
         self.assertEqual(p.stdin, None)
 
-    def test_cwd(self):
-        tmpdir = tempfile.gettempdir()
-        # We cannot use os.path.realpath to canonicalize the path,
-        # since it doesn't expand Tru64 {memb} strings. See bug 1063571.
-        cwd = os.getcwd()
-        os.chdir(tmpdir)
-        tmpdir = os.getcwd()
-        os.chdir(cwd)
-        p = subprocess.Popen([sys.executable, "-c",
-                              'import sys,os;'
-                              'sys.stdout.write(os.getcwd())'],
-                             stdout=subprocess.PIPE,
-                             cwd=tmpdir)
-        self.addCleanup(p.stdout.close)
-        normcase = os.path.normcase
-        self.assertEqual(normcase(p.stdout.read().decode("utf-8")),
-                         normcase(tmpdir))
-
     def test_env(self):
         newenv = os.environ.copy()
         newenv["FRUIT"] = "orange"