diff --git a/mypy/checkexpr.py b/mypy/checkexpr.py
index 2ed757eeeaa8..3c86529fc390 100644
--- a/mypy/checkexpr.py
+++ b/mypy/checkexpr.py
@@ -126,6 +126,7 @@
     covers_at_runtime,
     find_member,
     has_any_type,
+    is_proper_subtype,
     is_same_type,
     is_subtype,
     merge_typevars_in_callables_by_name,
@@ -6941,6 +6942,16 @@ def any_causes_overload_ambiguity(
                 for formal in formals:
                     matching_formals.append(matched_callable.arg_types[formal])
             if not all_same_types(matching_formals) and not all_same_types(matching_returns):
+                if (
+                    not arg_kinds[arg_idx].is_star()
+                    and not isinstance(get_proper_type(arg_type), FunctionLike)
+                    and all(is_proper_subtype(arg_type, formal) for formal in matching_formals)
+                ):
+                    # These matches do not depend on Any being compatible with arbitrary
+                    # types. For example, SubBox[Any] matches both SubBox[Any] and Box[Any].
+                    # Callable subtyping can still accept gradual parameter lists, so keep
+                    # the conservative ambiguity check for callable arguments.
+                    continue
                 # Any maps to multiple different types, and the return types of these items differ.
                 return True
 
diff --git a/test-data/unit/check-overloading.test b/test-data/unit/check-overloading.test
index cd5b924ed6b4..44463fc0ddcb 100644
--- a/test-data/unit/check-overloading.test
+++ b/test-data/unit/check-overloading.test
@@ -1812,6 +1812,27 @@ reveal_type(f(d))  # N: Revealed type is "builtins.list[builtins.int]"
 
 [builtins fixtures/list.pyi]
 
+[case testOverloadWithNestedAnyNotCausingAmbiguity]
+from typing import Any, Generic, TypeVar, overload
+T = TypeVar('T')
+
+class Box(Generic[T]): pass
+class SubBox(Box[T]): pass
+
+@overload
+def choose(value: SubBox[T]) -> SubBox[T]: ...
+@overload
+def choose(value: Box[T]) -> Box[T]: ...
+def choose(value): pass
+
+value: SubBox[Any]
+reveal_type(choose(value))  # N: Revealed type is "__main__.SubBox[Any]"
+reveal_type(choose(value=value))  # N: Revealed type is "__main__.SubBox[Any]"
+nested: SubBox[Box[Any]]
+reveal_type(choose(nested))  # N: Revealed type is "__main__.SubBox[__main__.Box[Any]]"
+any_value: Any
+reveal_type(choose(any_value))  # N: Revealed type is "Any"
+
 [case testOverloadWithOverlappingItemsAndAnyArgument10]
 from typing import overload, Any
 
diff --git a/test-data/unit/pythoneval.test b/test-data/unit/pythoneval.test
index 8c37e48d7c33..7c8af3ca2082 100644
--- a/test-data/unit/pythoneval.test
+++ b/test-data/unit/pythoneval.test
@@ -2287,6 +2287,20 @@ y = t"hello {1}"
 [out]
 m.pyi:3: error: T-strings: requires Python 3.14 or newer (current target: Python 3.13)
 
+[case testReversedListWithNestedAny]
+# flags: --python-version=3.12 --warn-return-any
+from typing import Any, assert_type
+
+def last_value(values: list[tuple[Any, int]]) -> int | None:
+    for key, value in reversed(values):
+        assert_type(value, int)
+        return value
+    return None
+
+assert last_value([('first', 1), ('last', 2)]) == 2
+assert last_value([]) is None
+[out]
+
 [case testNativeParserStarUnpackRequiresPython311]
 # flags: --python-version=3.10 --native-parser
 from typing_extensions import TypeVarTuple, Unpack