diff --git a/mypy/checkexpr.py b/mypy/checkexpr.py
index 172d44555b94..b4abb6e0677f 100644
--- a/mypy/checkexpr.py
+++ b/mypy/checkexpr.py
@@ -814,7 +814,7 @@ def validate_typeddict_kwargs(
         self, kwargs: Iterable[tuple[Expression | None, Expression]], callee: TypedDictType
     ) -> tuple[dict[str, list[Expression]], set[str]] | None:
         # All (actual or mapped from ** unpacks) expressions that can match given key.
-        result = defaultdict(list)
+        result: defaultdict[str, list[Expression]] = defaultdict(list)
         # Keys that are guaranteed to be present no matter what (e.g. for all items of a union)
         always_present_keys = set()
         # Indicates latest encountered ** unpack of a non-closed type among items.
@@ -837,9 +837,12 @@ def validate_typeddict_kwargs(
                     return None
                 else:
                     # A directly present key unconditionally shadows all previously found
-                    # values from ** items.
-                    # TODO: for duplicate keys, type-check all values.
-                    result[literal_value] = [item_arg]
+                    # values from ** items. Preserve directly present values, since their
+                    # expressions are still evaluated even when a later value shadows them.
+                    previous_values = [
+                        value for value in result[literal_value] if not isinstance(value, TempNode)
+                    ]
+                    result[literal_value] = [item_arg, *previous_values]
                     always_present_keys.add(literal_value)
             else:
                 is_valid, is_open = self.validate_star_typeddict_item(
@@ -917,11 +920,13 @@ def validate_star_typeddict_item(
                 # some `overrides` types are narrower that types in `defaults`, and
                 # former are too wide for `Config`.
                 if result[key]:
-                    first = result[key][0]
-                    if not isinstance(first, TempNode):
+                    explicit_values = [
+                        value for value in result[key] if not isinstance(value, TempNode)
+                    ]
+                    if explicit_values:
                         # We must always preserve any non-synthetic values, so that
-                        # we will accept them even if they are shadowed.
-                        result[key] = [first, arg]
+                        # we type-check them even if they are shadowed.
+                        result[key] = [*explicit_values, arg]
                     else:
                         result[key] = [arg]
                 else:
diff --git a/test-data/unit/check-typeddict.test b/test-data/unit/check-typeddict.test
index 01414ee2f457..609608b009de 100644
--- a/test-data/unit/check-typeddict.test
+++ b/test-data/unit/check-typeddict.test
@@ -79,6 +79,26 @@ p = Point(x='meaning_of_life', y=1337)  # E: Incompatible types (expression has
 [builtins fixtures/dict.pyi]
 [typing fixtures/typing-typeddict.pyi]
 
+[case testTypedDictDuplicateKeysTypeCheckAllValues]
+from typing import TypedDict
+
+class Payload(TypedDict):
+    value: int
+
+def takes_str(value: str) -> int:
+    return 0
+
+constructed = Payload({"value": takes_str(1), "value": 0})  # E: Argument 1 to "takes_str" has incompatible type "int"; expected "str"
+contextual: Payload = {"value": takes_str(1), "value": 0}  # E: Argument 1 to "takes_str" has incompatible type "int"; expected "str"
+overrides: Payload = {"value": 0}
+with_unpack = Payload({
+    "value": takes_str(1),  # E: Argument 1 to "takes_str" has incompatible type "int"; expected "str"
+    "value": takes_str(2),  # E: Argument 1 to "takes_str" has incompatible type "int"; expected "str"
+    **overrides,
+})
+[builtins fixtures/dict.pyi]
+[typing fixtures/typing-typeddict.pyi]
+
 [case testCannotCreateTypedDictInstanceWithInlineTypedDict]
 from typing import TypedDict
 D = TypedDict('D', {