diff --git a/Lib/test/test_grammar.py b/Lib/test/test_grammar.py
index 8507a07e498532..7c15a23a69163b 100644
--- a/Lib/test/test_grammar.py
+++ b/Lib/test/test_grammar.py
@@ -350,6 +350,11 @@ def test_var_annot_syntax_errors(self):
         check_syntax_error(self, "x: int: str")
         check_syntax_error(self, "def f():\n"
                                  "    nonlocal x: int\n")
+        check_syntax_error(self, "def f():\n"
+                                 "    global x: int\n")
+        check_syntax_error(self, "x: int = y = 1")
+        check_syntax_error(self, "z = w: int = 1")
+        check_syntax_error(self, "x: int = y: int = 1")
         # AST pass
         check_syntax_error(self, "[x, 0]: int\n")
         check_syntax_error(self, "f(): int\n")
@@ -363,6 +368,12 @@ def test_var_annot_syntax_errors(self):
         check_syntax_error(self, "def f():\n"
                                  "    global x\n"
                                  "    x: int\n")
+        check_syntax_error(self, "def f():\n"
+                                 "    x: int\n"
+                                 "    nonlocal x\n")
+        check_syntax_error(self, "def f():\n"
+                                 "    nonlocal x\n"
+                                 "    x: int\n")
 
     def test_var_annot_basic_semantics(self):
         # execution order