diff --git a/crates/ty_python_semantic/resources/mdtest/assignment/annotations.md b/crates/ty_python_semantic/resources/mdtest/assignment/annotations.md
index d97092720b..3865572726 100644
--- a/crates/ty_python_semantic/resources/mdtest/assignment/annotations.md
+++ b/crates/ty_python_semantic/resources/mdtest/assignment/annotations.md
@@ -310,6 +310,65 @@ reveal_type(s)  # revealed: list[Literal[1]]
 reveal_type(s)  # revealed: list[Literal[1]]
 ```
 
+## Generic constructor annotations are understood
+
+```toml
+[environment]
+python-version = "3.12"
+```
+
+```py
+from typing import Any
+
+class X[T]:
+    def __init__(self, value: T):
+        self.value = value
+
+a: X[int] = X(1)
+reveal_type(a)  # revealed: X[int]
+
+b: X[int | None] = X(1)
+reveal_type(b)  # revealed: X[int | None]
+
+c: X[int | None] | None = X(1)
+reveal_type(c)  # revealed: X[int | None]
+
+def _[T](a: X[T]):
+    b: X[T | int] = X(a.value)
+    reveal_type(b)  # revealed: X[T@_ | int]
+
+d: X[Any] = X(1)
+reveal_type(d)  # revealed: X[Any]
+
+def _(flag: bool):
+    # TODO: Handle unions correctly.
+    # error: [invalid-assignment] "Object of type `X[int]` is not assignable to `X[int | None]`"
+    a: X[int | None] = X(1) if flag else X(2)
+    reveal_type(a)  # revealed: X[int | None]
+```
+
+```py
+from dataclasses import dataclass
+
+@dataclass
+class Y[T]:
+    value: T
+
+y1: Y[Any] = Y(value=1)
+# TODO: This should reveal `Y[Any]`.
+reveal_type(y1)  # revealed: Y[int]
+```
+
+```py
+class Z[T]:
+    def __new__(cls, value: T):
+        return super().__new__(cls)
+
+z1: Z[Any] = Z(1)
+# TODO: This should reveal `Z[Any]`.
+reveal_type(z1)  # revealed: Z[int]
+```
+
 ## PEP-604 annotations are supported
 
 ```py
diff --git a/crates/ty_python_semantic/resources/mdtest/narrow/assignment.md b/crates/ty_python_semantic/resources/mdtest/narrow/assignment.md
index f692c59835..5786b465cd 100644
--- a/crates/ty_python_semantic/resources/mdtest/narrow/assignment.md
+++ b/crates/ty_python_semantic/resources/mdtest/narrow/assignment.md
@@ -206,7 +206,7 @@ dd: defaultdict[int, int] = defaultdict(int)
 dd[0] = 0
 cm: ChainMap[int, int] = ChainMap({1: 1}, {0: 0})
 cm[0] = 0
-reveal_type(cm)  # revealed: ChainMap[Unknown | int, Unknown | int]
+reveal_type(cm)  # revealed: ChainMap[int | Unknown, int | Unknown]
 
 reveal_type(l[0])  # revealed: Literal[0]
 reveal_type(d[0])  # revealed: Literal[0]
diff --git a/crates/ty_python_semantic/src/types.rs b/crates/ty_python_semantic/src/types.rs
index d49cf0087d..c9641c4e34 100644
--- a/crates/ty_python_semantic/src/types.rs
+++ b/crates/ty_python_semantic/src/types.rs
@@ -1111,6 +1111,22 @@ impl<'db> Type<'db> {
         }
     }
 
+    /// If the type is a generic class constructor, returns the class instance type.
+    pub(crate) fn synthesized_constructor_return_ty(self, db: &'db dyn Db) -> Option<Type<'db>> {
+        // TODO: This does not correctly handle unions or intersections. It also does not handle
+        // constructors that are not represented as bound methods, e.g. `__new__`, or synthesized
+        // dataclass initializers.
+        if let Type::BoundMethod(method) = self
+            && let Type::NominalInstance(instance) = method.self_instance(db)
+            && method.function(db).name(db).as_str() == "__init__"
+        {
+            let class_ty = instance.class_literal(db).identity_specialization(db);
+            Some(Type::instance(db, class_ty))
+        } else {
+            None
+        }
+    }
+
     pub const fn is_property_instance(&self) -> bool {
         matches!(self, Type::PropertyInstance(..))
     }
diff --git a/crates/ty_python_semantic/src/types/call/bind.rs b/crates/ty_python_semantic/src/types/call/bind.rs
index db1d06c32e..423783b420 100644
--- a/crates/ty_python_semantic/src/types/call/bind.rs
+++ b/crates/ty_python_semantic/src/types/call/bind.rs
@@ -2687,6 +2687,7 @@ struct ArgumentTypeChecker<'a, 'db> {
     arguments: &'a CallArguments<'a, 'db>,
     argument_matches: &'a [MatchedArgument<'db>],
     parameter_tys: &'a mut [Option<Type<'db>>],
+    callable_type: Type<'db>,
     call_expression_tcx: TypeContext<'db>,
     return_ty: Type<'db>,
     errors: &'a mut Vec<BindingError<'db>>,
@@ -2703,6 +2704,7 @@ impl<'a, 'db> ArgumentTypeChecker<'a, 'db> {
         arguments: &'a CallArguments<'a, 'db>,
         argument_matches: &'a [MatchedArgument<'db>],
         parameter_tys: &'a mut [Option<Type<'db>>],
+        callable_type: Type<'db>,
         call_expression_tcx: TypeContext<'db>,
         return_ty: Type<'db>,
         errors: &'a mut Vec<BindingError<'db>>,
@@ -2713,6 +2715,7 @@ impl<'a, 'db> ArgumentTypeChecker<'a, 'db> {
             arguments,
             argument_matches,
             parameter_tys,
+            callable_type,
             call_expression_tcx,
             return_ty,
             errors,
@@ -2754,8 +2757,9 @@ impl<'a, 'db> ArgumentTypeChecker<'a, 'db> {
         };
 
         let return_with_tcx = self
-            .signature
-            .return_ty
+            .callable_type
+            .synthesized_constructor_return_ty(self.db)
+            .or(self.signature.return_ty)
             .zip(self.call_expression_tcx.annotation);
 
         self.inferable_typevars = generic_context.inferable_typevars(self.db);
@@ -2763,7 +2767,9 @@ impl<'a, 'db> ArgumentTypeChecker<'a, 'db> {
 
         // Prefer the declared type of generic classes.
         let preferred_type_mappings = return_with_tcx.and_then(|(return_ty, tcx)| {
-            tcx.class_specialization(self.db)?;
+            tcx.filter_union(self.db, |ty| ty.class_specialization(self.db).is_some())
+                .class_specialization(self.db)?;
+
             builder.infer(return_ty, tcx).ok()?;
             Some(builder.type_mappings().clone())
         });
@@ -3196,6 +3202,7 @@ impl<'db> Binding<'db> {
             arguments,
             &self.argument_matches,
             &mut self.parameter_tys,
+            self.callable_type,
             call_expression_tcx,
             self.return_ty,
             &mut self.errors,
diff --git a/crates/ty_python_semantic/src/types/infer/builder.rs b/crates/ty_python_semantic/src/types/infer/builder.rs
index 74e8aca604..c227412752 100644
--- a/crates/ty_python_semantic/src/types/infer/builder.rs
+++ b/crates/ty_python_semantic/src/types/infer/builder.rs
@@ -6025,9 +6025,13 @@ impl<'db, 'ast> TypeInferenceBuilder<'db, 'ast> {
             // TODO: Checking assignability against the full declared type could help avoid
             // cases where the constraint solver is not smart enough to solve complex unions.
             // We should see revisit this after the new constraint solver is implemented.
-            if !speculated_bindings
-                .return_type(db)
-                .is_assignable_to(db, narrowed_ty)
+            if speculated_bindings
+                .callable_type()
+                .synthesized_constructor_return_ty(db)
+                .is_none()
+                && !speculated_bindings
+                    .return_type(db)
+                    .is_assignable_to(db, narrowed_ty)
             {
                 return None;
             }