diff --git a/Lib/test/test_syntax.py b/Lib/test/test_syntax.py
index f959bbb4400702..477879db2fd493 100644
--- a/Lib/test/test_syntax.py
+++ b/Lib/test/test_syntax.py
@@ -1877,6 +1877,68 @@ def f(x: *b)
^^^^^^^^^^^
SyntaxError: bytes can only contain ASCII literal characters
+Invalid expressions in type scopes:
+
+ >>> type A[T: (x:=3)] = int
+ Traceback (most recent call last):
+ ...
+ SyntaxError: named expression cannot be used within a TypeVar bound
+
+ >>> type A[T: (yield 3)] = int
+ Traceback (most recent call last):
+ ...
+ SyntaxError: yield expression cannot be used within a TypeVar bound
+
+ >>> type A[T: (await 3)] = int
+ Traceback (most recent call last):
+ ...
+ SyntaxError: await expression cannot be used within a TypeVar bound
+
+ >>> type A[T: (yield from [])] = int
+ Traceback (most recent call last):
+ ...
+ SyntaxError: yield expression cannot be used within a TypeVar bound
+
+ >>> type A = (x := 3)
+ Traceback (most recent call last):
+ ...
+ SyntaxError: named expression cannot be used within a type alias
+
+ >>> type A = (yield 3)
+ Traceback (most recent call last):
+ ...
+ SyntaxError: yield expression cannot be used within a type alias
+
+ >>> type A = (await 3)
+ Traceback (most recent call last):
+ ...
+ SyntaxError: await expression cannot be used within a type alias
+
+ >>> type A = (yield from [])
+ Traceback (most recent call last):
+ ...
+ SyntaxError: yield expression cannot be used within a type alias
+
+ >>> class A[T]((x := 3)): ...
+ Traceback (most recent call last):
+ ...
+ SyntaxError: named expression cannot be used within the definition of a generic
+
+ >>> class A[T]((yield 3)): ...
+ Traceback (most recent call last):
+ ...
+ SyntaxError: yield expression cannot be used within the definition of a generic
+
+ >>> class A[T]((await 3)): ...
+ Traceback (most recent call last):
+ ...
+ SyntaxError: await expression cannot be used within the definition of a generic
+
+ >>> class A[T]((yield from [])): ...
+ Traceback (most recent call last):
+ ...
+ SyntaxError: yield expression cannot be used within the definition of a generic
+
"""
import re
diff --git a/Misc/NEWS.d/next/Core and Builtins/2023-05-16-19-17-48.gh-issue-104572.eBZQYS.rst b/Misc/NEWS.d/next/Core and Builtins/2023-05-16-19-17-48.gh-issue-104572.eBZQYS.rst
new file mode 100644
index 00000000000000..25bad8aa6e3e6f
--- /dev/null
+++ b/Misc/NEWS.d/next/Core and Builtins/2023-05-16-19-17-48.gh-issue-104572.eBZQYS.rst
@@ -0,0 +1,2 @@
+Improve syntax error message for invalid constructs in :pep:`695` contexts
+and in annotations when ``from __future__ import annotations`` is active.
diff --git a/Python/symtable.c b/Python/symtable.c
index 3451f6c7bffb6d..f896f7cbe3382b 100644
--- a/Python/symtable.c
+++ b/Python/symtable.c
@@ -45,16 +45,16 @@
"assignment expression cannot be used in a comprehension iterable expression"
#define ANNOTATION_NOT_ALLOWED \
-"'%s' can not be used within an annotation"
+"%s cannot be used within an annotation"
#define TYPEVAR_BOUND_NOT_ALLOWED \
-"'%s' can not be used within a TypeVar bound"
+"%s cannot be used within a TypeVar bound"
#define TYPEALIAS_NOT_ALLOWED \
-"'%s' can not be used within a type alias"
+"%s cannot be used within a type alias"
#define TYPEPARAM_NOT_ALLOWED \
-"'%s' can not be used within the definition of a generic"
+"%s cannot be used within the definition of a generic"
#define DUPLICATE_TYPE_PARAM \
"duplicate type parameter '%U'"
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