diff --git a/crates/ty_python_semantic/resources/mdtest/generics/legacy/functions.md b/crates/ty_python_semantic/resources/mdtest/generics/legacy/functions.md
index e0625c3fb31e8..21b574b78ea4f 100644
--- a/crates/ty_python_semantic/resources/mdtest/generics/legacy/functions.md
+++ b/crates/ty_python_semantic/resources/mdtest/generics/legacy/functions.md
@@ -673,6 +673,27 @@ def decorated(t: T) -> None:
     reveal_type(cast(T, t))  # revealed: T@decorated
 ```
 
+## Attribute access on `Callable`-bounded TypeVars
+
+```py
+from typing import Callable, Generic, TypeVar
+
+F = TypeVar("F", bound=Callable)
+
+def my_decorator(f: F) -> None:
+    # error: [unresolved-attribute]
+    f.whatever
+    # error: [unresolved-attribute]
+    f.whatever = 1
+
+class Box(Generic[F]):
+    cls: type[F]
+
+def specialized(box: Box[Callable]) -> None:
+    # error: [unresolved-attribute]
+    box.cls.whatever
+```
+
 ## Solving TypeVars with upper bounds in unions
 
 ```py
diff --git a/crates/ty_python_semantic/resources/mdtest/generics/pep695/functions.md b/crates/ty_python_semantic/resources/mdtest/generics/pep695/functions.md
index b69350c98b1fb..406629542135c 100644
--- a/crates/ty_python_semantic/resources/mdtest/generics/pep695/functions.md
+++ b/crates/ty_python_semantic/resources/mdtest/generics/pep695/functions.md
@@ -716,6 +716,25 @@ def decorated[T](t: T) -> None:
     reveal_type(cast(T, t))  # revealed: T@decorated
 ```
 
+## Attribute access on `Callable`-bounded TypeVars
+
+```py
+from typing import Callable
+
+def my_decorator[T: Callable](f: T) -> None:
+    # error: [unresolved-attribute]
+    f.whatever
+    # error: [unresolved-attribute]
+    f.whatever = 1
+
+class Box[T: Callable]:
+    cls: type[T]
+
+def specialized(box: Box[Callable]) -> None:
+    # error: [unresolved-attribute]
+    box.cls.whatever
+```
+
 ## Solving TypeVars with upper bounds in unions
 
 ```py
diff --git a/crates/ty_python_semantic/resources/mdtest/type_of/generics.md b/crates/ty_python_semantic/resources/mdtest/type_of/generics.md
index e0bb86ef45ff7..f7f2a14c1085b 100644
--- a/crates/ty_python_semantic/resources/mdtest/type_of/generics.md
+++ b/crates/ty_python_semantic/resources/mdtest/type_of/generics.md
@@ -331,8 +331,7 @@ def f2[T](x: T) -> type[T]:
 reveal_type(f2(int(1)))  # revealed: type[int]
 reveal_type(f2(object()))  # revealed: type
 
-# TODO: This should reveal `type[Literal[1]]`.
-reveal_type(f2(1))  # revealed: type[Unknown]
+reveal_type(f2(1))  # revealed: <class 'int'>
 
 def f3[T](x: type[T]) -> T:
     return x()
diff --git a/crates/ty_python_semantic/src/types/subclass_of.rs b/crates/ty_python_semantic/src/types/subclass_of.rs
index 42241a6153499..a0ec57a9f1296 100644
--- a/crates/ty_python_semantic/src/types/subclass_of.rs
+++ b/crates/ty_python_semantic/src/types/subclass_of.rs
@@ -163,8 +163,7 @@ impl<'db> SubclassOfType<'db> {
                 if mapped.is_never() {
                     Type::Never
                 } else {
-                    SubclassOfType::try_from_instance(db, mapped)
-                        .unwrap_or(SubclassOfType::subclass_of_unknown())
+                    mapped.to_meta_type(db)
                 }
             }
         }
@@ -460,16 +459,12 @@ impl<'db> SubclassOfInner<'db> {
                         .unwrap_or(SubclassOfType::subclass_of_unknown()),
                 ),
                 Some(TypeVarBoundOrConstraints::UpperBound(bound)) => {
-                    TypeVarBoundOrConstraints::UpperBound(
-                        SubclassOfType::try_from_instance(db, bound)
-                            .unwrap_or(SubclassOfType::subclass_of_unknown()),
-                    )
+                    TypeVarBoundOrConstraints::UpperBound(bound.to_meta_type(db))
                 }
                 Some(TypeVarBoundOrConstraints::Constraints(constraints)) => {
-                    TypeVarBoundOrConstraints::Constraints(constraints.map(db, |constraint| {
-                        SubclassOfType::try_from_instance(db, *constraint)
-                            .unwrap_or(SubclassOfType::subclass_of_unknown())
-                    }))
+                    TypeVarBoundOrConstraints::Constraints(
+                        constraints.map(db, |constraint| constraint.to_meta_type(db)),
+                    )
                 }
             })
         });