diff --git a/mypy/constraints.py b/mypy/constraints.py
index 48cc23f74222..1aa6b4200a85 100644
--- a/mypy/constraints.py
+++ b/mypy/constraints.py
@@ -424,7 +424,15 @@ def _infer_constraints(
         )
         if result:
             return result
-        elif has_recursive_types(template) and not has_recursive_types(actual):
+        elif (
+            has_recursive_types(template)
+            or (
+                any(isinstance(t, TypeVarType) for t in template.items)
+                and any(
+                    not isinstance(t, TypeVarType) and has_type_vars(t) for t in template.items
+                )
+            )
+        ) and not has_recursive_types(actual):
             return handle_recursive_union(template, actual, direction)
         return []
 
@@ -504,11 +512,13 @@ def merge_with_any(constraint: Constraint) -> Constraint:
 
 
 def handle_recursive_union(template: UnionType, actual: Type, direction: int) -> list[Constraint]:
-    # This is a hack to special-case things like Union[T, Inst[T]] in recursive types. Although
-    # it is quite arbitrary, it is a relatively common pattern, so we should handle it well.
-    # This function may be called when inferring against such union resulted in different
-    # constraints for each item. Normally we give up in such case, but here we instead split
-    # the union in two parts, and try inferring sequentially.
+    # Special-case unions of the form ``T | Wrapper[T]``, both in recursive type aliases and
+    # in plain generic function signatures (e.g. ``def f[T](x: T | list[T])``).
+    # When any_constraints() infers against each union branch independently it may yield
+    # conflicting results — e.g. ``T >= list[int]`` from the bare-T branch and ``T = int``
+    # from the ``list[T]`` branch — and gives up, leaving T unconstrained.  Instead, we
+    # split the union into non-TypeVar parts (tried first, since they give precise bounds
+    # like ``T = int``) and TypeVar parts (used as a fallback).
     non_type_var_items = [t for t in template.items if not isinstance(t, TypeVarType)]
     type_var_items = [t for t in template.items if isinstance(t, TypeVarType)]
     return infer_constraints(
diff --git a/test-data/unit/check-inference.test b/test-data/unit/check-inference.test
index a5b3ae7238a5..47d6f9ad9ff2 100644
--- a/test-data/unit/check-inference.test
+++ b/test-data/unit/check-inference.test
@@ -873,13 +873,7 @@ def g(x: Union[T, List[T]]) -> List[T]: pass
 def h(x: List[str]) -> None: pass
 g('a')() # E: "list[str]" not callable
 
-# The next line is a case where there are multiple ways to satisfy a constraint
-# involving a Union. Either T = list[str] or T = str would turn out to be valid,
-# but mypy doesn't know how to branch on these two options (and potentially have
-# to backtrack later) and defaults to T = Never. The result is an
-# awkward error message. Either a better error message, or simply accepting the
-# call, would be preferable here.
-g(['a']) # E: Argument 1 to "g" has incompatible type "list[str]"; expected "list[Never]"
+g(['a'])
 
 h(g(['a']))
 
@@ -891,6 +885,20 @@ i(b, a, b)
 i(a, b, b) # E: Argument 1 to "i" has incompatible type "list[int]"; expected "list[str]"
 [builtins fixtures/list.pyi]
 
+[case testUnionInferenceTypeVarWrapper]
+# Regression test for https://github.com/python/mypy/issues/21615
+# T | Wrapper[T] should infer T from the wrapped branch when the argument matches it.
+from typing import TypeVar, Union, List, Dict
+T = TypeVar('T')
+def f(x: Union[T, List[T]]) -> List[T]: pass
+def g(x: Union[T, Dict[str, T]]) -> T: pass
+
+reveal_type(f(1))      # N: Revealed type is "builtins.list[builtins.int]"
+reveal_type(f([1]))    # N: Revealed type is "builtins.list[builtins.int]"
+reveal_type(f(['a']))  # N: Revealed type is "builtins.list[builtins.str]"
+reveal_type(g({'k': 1}))  # N: Revealed type is "builtins.int"
+[builtins fixtures/dict.pyi]
+
 [case testCallableListJoinInference]
 from typing import Any, Callable