diff --git a/mypy/binder.py b/mypy/binder.py
index d3482d1dad4f..2ae58dad1fe0 100644
--- a/mypy/binder.py
+++ b/mypy/binder.py
@@ -138,6 +138,10 @@ def __init__(self, options: Options) -> None:
         # flexible inference of variable types (--allow-redefinition-new).
         self.bind_all = options.allow_redefinition_new
 
+        # This tracks any externally visible changes in binder to invalidate
+        # expression caches when needed.
+        self.version = 0
+
     def _get_id(self) -> int:
         self.next_id += 1
         return self.next_id
@@ -158,6 +162,7 @@ def push_frame(self, conditional_frame: bool = False) -> Frame:
         return f
 
     def _put(self, key: Key, type: Type, from_assignment: bool, index: int = -1) -> None:
+        self.version += 1
         self.frames[index].types[key] = CurrentType(type, from_assignment)
 
     def _get(self, key: Key, index: int = -1) -> CurrentType | None:
@@ -185,6 +190,7 @@ def put(self, expr: Expression, typ: Type, *, from_assignment: bool = True) -> N
         self._put(key, typ, from_assignment)
 
     def unreachable(self) -> None:
+        self.version += 1
         self.frames[-1].unreachable = True
 
     def suppress_unreachable_warnings(self) -> None:
diff --git a/mypy/checker.py b/mypy/checker.py
index 7579c36a97d0..4e78755aa153 100644
--- a/mypy/checker.py
+++ b/mypy/checker.py
@@ -448,7 +448,6 @@ def reset(self) -> None:
         self.binder = ConditionalTypeBinder(self.options)
         self._type_maps[1:] = []
         self._type_maps[0].clear()
-        self.temp_type_map = None
         self.expr_checker.reset()
         self.deferred_nodes = []
         self.partial_types = []
@@ -3019,6 +3018,8 @@ def visit_block(self, b: Block) -> None:
                     break
             else:
                 self.accept(s)
+                # Clear expression cache after each statement to avoid unlimited growth.
+                self.expr_checker.expr_cache.clear()
 
     def should_report_unreachable_issues(self) -> bool:
         return (
@@ -4000,7 +4001,7 @@ def check_multi_assignment_from_union(
                 for t, lv in zip(transposed, self.flatten_lvalues(lvalues)):
                     # We can access _type_maps directly since temporary type maps are
                     # only created within expressions.
-                    t.append(self._type_maps[0].pop(lv, AnyType(TypeOfAny.special_form)))
+                    t.append(self._type_maps[-1].pop(lv, AnyType(TypeOfAny.special_form)))
         union_types = tuple(make_simplified_union(col) for col in transposed)
         for expr, items in assignments.items():
             # Bind a union of types collected in 'assignments' to every expression.
@@ -4659,6 +4660,8 @@ def replace_partial_type(
     ) -> None:
         """Replace the partial type of var with a non-partial type."""
         var.type = new_type
+        # Updating a partial type should invalidate expression caches.
+        self.binder.version += 1
         del partial_types[var]
         if self.options.allow_redefinition_new:
             # When using --allow-redefinition-new, binder tracks all types of
diff --git a/mypy/checkexpr.py b/mypy/checkexpr.py
index 86f8d9410476..ed0f9900c2f4 100644
--- a/mypy/checkexpr.py
+++ b/mypy/checkexpr.py
@@ -19,7 +19,7 @@
 from mypy.checkmember import analyze_member_access, has_operator
 from mypy.checkstrformat import StringFormatterChecker
 from mypy.erasetype import erase_type, remove_instance_last_known_values, replace_meta_vars
-from mypy.errors import ErrorWatcher, report_internal_error
+from mypy.errors import ErrorInfo, ErrorWatcher, report_internal_error
 from mypy.expandtype import (
     expand_type,
     expand_type_by_instance,
@@ -355,9 +355,15 @@ def __init__(
         type_state.infer_polymorphic = not self.chk.options.old_type_inference
 
         self._arg_infer_context_cache = None
+        self.expr_cache: dict[
+            tuple[Expression, Type | None],
+            tuple[int, Type, list[ErrorInfo], dict[Expression, Type]],
+        ] = {}
+        self.in_lambda_expr = False
 
     def reset(self) -> None:
         self.resolved_type = {}
+        self.expr_cache.clear()
 
     def visit_name_expr(self, e: NameExpr) -> Type:
         """Type check a name expression.
@@ -5404,6 +5410,8 @@ def find_typeddict_context(
 
     def visit_lambda_expr(self, e: LambdaExpr) -> Type:
         """Type check lambda expression."""
+        old_in_lambda = self.in_lambda_expr
+        self.in_lambda_expr = True
         self.chk.check_default_args(e, body_is_trivial=False)
         inferred_type, type_override = self.infer_lambda_type_using_context(e)
         if not inferred_type:
@@ -5424,6 +5432,7 @@ def visit_lambda_expr(self, e: LambdaExpr) -> Type:
                 ret_type = self.accept(e.expr(), allow_none_return=True)
             fallback = self.named_type("builtins.function")
             self.chk.return_types.pop()
+            self.in_lambda_expr = old_in_lambda
             return callable_type(e, fallback, ret_type)
         else:
             # Type context available.
@@ -5436,6 +5445,7 @@ def visit_lambda_expr(self, e: LambdaExpr) -> Type:
                     self.accept(e.expr(), allow_none_return=True)
             ret_type = self.chk.lookup_type(e.expr())
             self.chk.return_types.pop()
+            self.in_lambda_expr = old_in_lambda
             return replace_callable_return_type(inferred_type, ret_type)
 
     def infer_lambda_type_using_context(
@@ -5980,6 +5990,24 @@ def accept(
                 typ = self.visit_conditional_expr(node, allow_none_return=True)
             elif allow_none_return and isinstance(node, AwaitExpr):
                 typ = self.visit_await_expr(node, allow_none_return=True)
+            # Deeply nested generic calls can deteriorate performance dramatically.
+            # Although in most cases caching makes little difference, in worst case
+            # it avoids exponential complexity.
+            # We cannot use cache inside lambdas, because they skip immediate type
+            # context, and use enclosing one, see infer_lambda_type_using_context().
+            # TODO: consider using cache for more expression kinds.
+            elif isinstance(node, (CallExpr, ListExpr, TupleExpr)) and not (
+                self.in_lambda_expr or self.chk.current_node_deferred
+            ):
+                if (node, type_context) in self.expr_cache:
+                    binder_version, typ, messages, type_map = self.expr_cache[(node, type_context)]
+                    if binder_version == self.chk.binder.version:
+                        self.chk.store_types(type_map)
+                        self.msg.add_errors(messages)
+                    else:
+                        typ = self.accept_maybe_cache(node, type_context=type_context)
+                else:
+                    typ = self.accept_maybe_cache(node, type_context=type_context)
             else:
                 typ = node.accept(self)
         except Exception as err:
@@ -6010,6 +6038,21 @@ def accept(
             self.in_expression = False
         return result
 
+    def accept_maybe_cache(self, node: Expression, type_context: Type | None = None) -> Type:
+        binder_version = self.chk.binder.version
+        # Micro-optimization: inline local_type_map() as it is somewhat slow in mypyc.
+        type_map: dict[Expression, Type] = {}
+        self.chk._type_maps.append(type_map)
+        with self.msg.filter_errors(filter_errors=True, save_filtered_errors=True) as msg:
+            typ = node.accept(self)
+        messages = msg.filtered_errors()
+        if binder_version == self.chk.binder.version and not self.chk.current_node_deferred:
+            self.expr_cache[(node, type_context)] = (binder_version, typ, messages, type_map)
+        self.chk._type_maps.pop()
+        self.chk.store_types(type_map)
+        self.msg.add_errors(messages)
+        return typ
+
     def named_type(self, name: str) -> Instance:
         """Return an instance type with type given by the name and no type
         arguments. Alias for TypeChecker.named_type.
diff --git a/mypy/errors.py b/mypy/errors.py
index 5c135146bcb7..d75c1c62a1ed 100644
--- a/mypy/errors.py
+++ b/mypy/errors.py
@@ -390,7 +390,7 @@ class Errors:
     # in some cases to avoid reporting huge numbers of errors.
     seen_import_error = False
 
-    _watchers: list[ErrorWatcher] = []
+    _watchers: list[ErrorWatcher]
 
     def __init__(
         self,
@@ -421,6 +421,7 @@ def initialize(self) -> None:
         self.scope = None
         self.target_module = None
         self.seen_import_error = False
+        self._watchers = []
 
     def reset(self) -> None:
         self.initialize()
@@ -931,7 +932,8 @@ def prefer_simple_messages(self) -> bool:
         if self.file in self.ignored_files:
             # Errors ignored, so no point generating fancy messages
             return True
-        for _watcher in self._watchers:
+        if self._watchers:
+            _watcher = self._watchers[-1]
             if _watcher._filter is True and _watcher._filtered is None:
                 # Errors are filtered
                 return True
diff --git a/test-data/unit/check-overloading.test b/test-data/unit/check-overloading.test
index 0f0fc8747223..22221416f151 100644
--- a/test-data/unit/check-overloading.test
+++ b/test-data/unit/check-overloading.test
@@ -6801,3 +6801,26 @@ class D(Generic[T]):
 a: D[str]  # E: Type argument "str" of "D" must be a subtype of "C"
 reveal_type(a.f(1))  # N: Revealed type is "builtins.int"
 reveal_type(a.f("x"))  # N: Revealed type is "builtins.str"
+
+[case testMultiAssignFromUnionInOverloadCached]
+from typing import Iterable, overload, Union, Optional
+
+@overload
+def always_bytes(str_or_bytes: None) -> None: ...
+@overload
+def always_bytes(str_or_bytes: Union[str, bytes]) -> bytes: ...
+def always_bytes(str_or_bytes: Union[None, str, bytes]) -> Optional[bytes]:
+    pass
+
+class Headers:
+    def __init__(self, iter: Iterable[tuple[bytes, bytes]]) -> None: ...
+
+headers: Union[Headers, dict[Union[str, bytes], Union[str, bytes]], Iterable[tuple[bytes, bytes]]]
+
+if isinstance(headers, dict):
+    headers = Headers(
+        (always_bytes(k), always_bytes(v)) for k, v in headers.items()
+    )
+
+reveal_type(headers)  # N: Revealed type is "Union[__main__.Headers, typing.Iterable[tuple[builtins.bytes, builtins.bytes]]]"
+[builtins fixtures/isinstancelist.pyi]
diff --git a/test-data/unit/fixtures/isinstancelist.pyi b/test-data/unit/fixtures/isinstancelist.pyi
index 0ee5258ff74b..2a43606f361a 100644
--- a/test-data/unit/fixtures/isinstancelist.pyi
+++ b/test-data/unit/fixtures/isinstancelist.pyi
@@ -26,6 +26,7 @@ class bool(int): pass
 class str:
     def __add__(self, x: str) -> str: pass
     def __getitem__(self, x: int) -> str: pass
+class bytes: pass
 
 T = TypeVar('T')
 KT = TypeVar('KT')
@@ -52,6 +53,7 @@ class dict(Mapping[KT, VT]):
     def __setitem__(self, k: KT, v: VT) -> None: pass
     def __iter__(self) -> Iterator[KT]: pass
     def update(self, a: Mapping[KT, VT]) -> None: pass
+    def items(self) -> Iterable[Tuple[KT, VT]]: pass
 
 class set(Generic[T]):
     def __iter__(self) -> Iterator[T]: pass