diff --git a/mypy/constraints.py b/mypy/constraints.py
index efb277ede1d0..e54983c9744f 100644
--- a/mypy/constraints.py
+++ b/mypy/constraints.py
@@ -557,11 +557,13 @@ def any_constraints(options: list[list[Constraint] | None], *, eager: bool) -> l
         # Multiple sets of constraints that are all the same. Just pick any one of them.
         return valid_options[0]
 
-    if all(is_similar_constraints(valid_options[0], c) for c in valid_options[1:]):
+    # This special-casing is not safe for ParamSpecs and TypeVarTuples, since unions are
+    # not valid constraints for them. This is however only needed in niche edge cases.
+    if all(is_similar_constraints(valid_options[0], c) for c in valid_options[1:]) and all(
+        isinstance(c.origin_type_var, TypeVarType) for c in valid_options[0]
+    ):
         # All options have same structure. In this case we can merge-in trivial
         # options (i.e. those that only have Any) and try again.
-        # TODO: More generally, if a given (variable, direction) pair appears in
-        # every option, combine the bounds with meet/join always, not just for Any.
         trivial_options = select_trivial(valid_options)
         if trivial_options and len(trivial_options) < len(valid_options):
             merged_options = []
@@ -1422,7 +1424,13 @@ def infer_against_any(self, types: Iterable[Type], any_type: AnyType) -> list[Co
         for t in flatten_nested_tuples(types):
             if isinstance(t, UnpackType):
                 if isinstance(t.type, TypeVarTupleType):
-                    res.append(Constraint(t.type, self.direction, any_type))
+                    res.append(
+                        Constraint(
+                            t.type,
+                            self.direction,
+                            t.type.tuple_fallback.copy_modified(args=[any_type]),
+                        )
+                    )
                 else:
                     unpacked = get_proper_type(t.type)
                     assert isinstance(unpacked, Instance)
diff --git a/test-data/unit/check-parameter-specification.test b/test-data/unit/check-parameter-specification.test
index 795af772f5fb..2441770b5598 100644
--- a/test-data/unit/check-parameter-specification.test
+++ b/test-data/unit/check-parameter-specification.test
@@ -2800,3 +2800,20 @@ def takes_paramspec(f: Callable[P, object]) -> bool:
 def run(callback: Callable[[Concatenate[int, ...]], None]) -> None:  # E: Concatenate is only valid as the first argument to Callable
     takes_paramspec(callback)
 [builtins fixtures/paramspec.pyi]
+
+[case testParamSpecApplyResultsFromUnionWithAnyNoCrash]
+from typing import Any, Callable, Generic, Union
+from typing_extensions import ParamSpec
+
+P = ParamSpec("P")
+class C(Generic[P]): ...
+
+def foo(c: Callable[P, None]) -> C[P]: ...
+
+x: Union[Any, C[[Any, Any]]]
+
+def test(x: int) -> None: ...
+
+x = foo(test)  # E: Argument 1 to "foo" has incompatible type "Callable[[int], None]"; expected "Callable[[Any, Any], None]"
+reveal_type(x)  # N: Revealed type is "__main__.C[[Any, Any]]"
+[builtins fixtures/paramspec.pyi]
diff --git a/test-data/unit/check-typevar-tuple.test b/test-data/unit/check-typevar-tuple.test
index 6d8c69a147a3..5449613aa3c5 100644
--- a/test-data/unit/check-typevar-tuple.test
+++ b/test-data/unit/check-typevar-tuple.test
@@ -3255,3 +3255,21 @@ class K(Base):
 class Base: ...
 reveal_type(K.q)  # N: Revealed type is "builtins.list[tuple[builtins.bool, builtins.int, builtins.str]]"
 [builtins fixtures/tuple.pyi]
+
+[case testTypeVarTupleApplyResultsFromUnionWithAnyNoCrash]
+from typing import Any, Generic, Union
+from typing_extensions import TypeVarTuple, Unpack
+
+Ts = TypeVarTuple("Ts")
+class C(Generic[Unpack[Ts]]): ...
+
+def foo(t: tuple[Unpack[Ts]]) -> C[Unpack[Ts]]: ...
+def bar(c: C[Unpack[Ts]]) -> tuple[Unpack[Ts]]: ...
+
+x: Union[Any, C[Unpack[tuple[int, ...]]]]
+x = foo((1, 2))
+reveal_type(x)  # N: Revealed type is "__main__.C[builtins.int, builtins.int]"
+
+y: Union[Any, C[Unpack[tuple[int, ...]]]]
+reveal_type(bar(y))  # N: Revealed type is "builtins.tuple[Any, ...]"
+[builtins fixtures/tuple.pyi]