diff --git a/mypy/checkexpr.py b/mypy/checkexpr.py
index b8f9bf087467..d9e0d4364916 100644
--- a/mypy/checkexpr.py
+++ b/mypy/checkexpr.py
@@ -113,6 +113,7 @@
 from mypy.semanal_enum import ENUM_BASES
 from mypy.state import state
 from mypy.subtypes import (
+    covers_at_runtime,
     find_member,
     is_equivalent,
     is_same_type,
@@ -4037,14 +4038,21 @@ def lookup_definer(typ: Instance, attr_name: str) -> str | None:
 
             variants_raw = [(op_name, left_op, left_type, right_expr)]
         elif (
-            is_subtype(right_type, left_type)
-            and isinstance(left_type, Instance)
-            and isinstance(right_type, Instance)
-            and not (
-                left_type.type.alt_promote is not None
-                and left_type.type.alt_promote.type is right_type.type
+            (
+                # Checking (A implies B) using the logically equivalent (not A or B), where
+                #    A: left and right are both `Instance` objects
+                #    B: right's __rop__ method is different from left's __op__ method
+                not (isinstance(left_type, Instance) and isinstance(right_type, Instance))
+                or (
+                    lookup_definer(left_type, op_name) != lookup_definer(right_type, rev_op_name)
+                    and (
+                        left_type.type.alt_promote is None
+                        or left_type.type.alt_promote.type is not right_type.type
+                    )
+                )
             )
-            and lookup_definer(left_type, op_name) != lookup_definer(right_type, rev_op_name)
+            # Note: use `covers_at_runtime` instead of `is_subtype` (#19006)
+            and covers_at_runtime(right_type, left_type)
         ):
             # When we do "A() + B()" where B is a subclass of A, we'll actually try calling
             # B's __radd__ method first, but ONLY if B explicitly defines or overrides the
diff --git a/test-data/unit/check-expressions.test b/test-data/unit/check-expressions.test
index ea6eac9a39b3..85cd18050a34 100644
--- a/test-data/unit/check-expressions.test
+++ b/test-data/unit/check-expressions.test
@@ -681,6 +681,29 @@ class B:
 s: str
 s = A() + B() # E: Unsupported operand types for + ("A" and "B")
 
+
+[case testReverseBinaryOperator4]
+from typing import assert_type, Never
+
+class Size(tuple[int, ...]):
+    def __add__(self, other: tuple[int, ...], /) -> "Size": return Size()  # type: ignore[override]
+    def __radd__(self, other: tuple[int, ...], /) -> "Size": return Size()
+
+size: Size = Size([3, 4])
+tup0: tuple[()] = ()
+tup1: tuple[int] = (1,)
+tup2: tuple[int, int] = (1, 2)
+tupN: tuple[int, ...] = (1, 2, 3)
+tupX: tuple[Never, ...] = ()
+
+assert_type(tup0 + size, Size)
+assert_type(tup1 + size, Size)
+assert_type(tup2 + size, Size)
+assert_type(tupN + size, Size)
+assert_type(tupX + size, Size)
+
+[builtins fixtures/tuple-typeshed.pyi]
+
 [case testBinaryOperatorWithAnyRightOperand]
 from typing import Any, cast
 class A: pass
diff --git a/test-data/unit/fixtures/tuple-typeshed.pyi b/test-data/unit/fixtures/tuple-typeshed.pyi
new file mode 100644
index 000000000000..57a1a29a87ad
--- /dev/null
+++ b/test-data/unit/fixtures/tuple-typeshed.pyi
@@ -0,0 +1,59 @@
+# tuple definition from typeshed,
+from typing import (
+    Generic,
+    Sequence,
+    TypeVar,
+    Iterable,
+    Iterator,
+    Any,
+    overload,
+    Self,
+    Protocol,
+)
+from types import GenericAlias
+
+_T = TypeVar("_T")
+_T_co = TypeVar('_T_co', covariant=True)
+
+class tuple(Sequence[_T_co], Generic[_T_co]):
+    def __new__(cls, iterable: Iterable[_T_co] = ..., /) -> Self: ...
+    def __len__(self) -> int: ...
+    def __contains__(self, key: object, /) -> bool: ...
+    @overload
+    def __getitem__(self, key: SupportsIndex, /) -> _T_co: ...
+    @overload
+    def __getitem__(self, key: slice, /) -> tuple[_T_co, ...]: ...
+    def __iter__(self) -> Iterator[_T_co]: ...
+    def __lt__(self, value: tuple[_T_co, ...], /) -> bool: ...
+    def __le__(self, value: tuple[_T_co, ...], /) -> bool: ...
+    def __gt__(self, value: tuple[_T_co, ...], /) -> bool: ...
+    def __ge__(self, value: tuple[_T_co, ...], /) -> bool: ...
+    def __eq__(self, value: object, /) -> bool: ...
+    def __hash__(self) -> int: ...
+    @overload
+    def __add__(self, value: tuple[_T_co, ...], /) -> tuple[_T_co, ...]: ...
+    @overload
+    def __add__(self, value: tuple[_T, ...], /) -> tuple[_T_co | _T, ...]: ...
+    def __mul__(self, value: SupportsIndex, /) -> tuple[_T_co, ...]: ...
+    def __rmul__(self, value: SupportsIndex, /) -> tuple[_T_co, ...]: ...
+    def count(self, value: Any, /) -> int: ...
+    def index(self, value: Any, start: SupportsIndex = ..., stop: SupportsIndex = ..., /) -> int: ...
+    def __class_getitem__(cls, item: Any, /) -> GenericAlias: ...
+
+class dict: pass
+class int: pass
+class slice: pass
+class bool(int): pass
+class str: pass # For convenience
+class object: pass
+class type: pass
+class ellipsis: pass
+class SupportsIndex(Protocol):
+    def __index__(self) -> int: pass
+class list(Sequence[_T], Generic[_T]):
+    @overload
+    def __getitem__(self, i: int) -> _T: ...
+    @overload
+    def __getitem__(self, s: slice) -> list[_T]: ...
+    def __contains__(self, item: object) -> bool: ...
+    def __iter__(self) -> Iterator[_T]: ...