diff --git a/crates/ty_python_semantic/resources/mdtest/assignment/annotations.md b/crates/ty_python_semantic/resources/mdtest/assignment/annotations.md
index 62852bc0ba..a8e064c3b5 100644
--- a/crates/ty_python_semantic/resources/mdtest/assignment/annotations.md
+++ b/crates/ty_python_semantic/resources/mdtest/assignment/annotations.md
@@ -234,3 +234,48 @@ reveal_type(x)  # revealed: Foo
 x: int = 1
 reveal_type(x) # revealed: Literal[1]
 ```
+
+## Annotations influence generic call inference
+
+```toml
+[environment]
+python-version = "3.12"
+```
+
+```py
+from typing import Literal
+
+def f[T](x: T) -> list[T]:
+    return [x]
+
+a = f("a")
+reveal_type(a)  # revealed: list[Literal["a"]]
+
+b: list[int | Literal["a"]] = f("a")
+reveal_type(b)  # revealed: list[int | Literal["a"]]
+
+c: list[int | str] = f("a")
+reveal_type(c)  # revealed: list[int | str]
+
+d: list[int | tuple[int, int]] = f((1, 2))
+reveal_type(d)  # revealed: list[int | tuple[int, int]]
+
+e: list[int] = f(True)
+reveal_type(e)  # revealed: list[int]
+
+# TODO: the RHS should be inferred as `list[Literal["a"]]` here
+# error: [invalid-assignment] "Object of type `list[int | Literal["a"]]` is not assignable to `list[int]`"
+g: list[int] = f("a")
+
+# error: [invalid-assignment] "Object of type `list[Literal["a"]]` is not assignable to `tuple[int]`"
+h: tuple[int] = f("a")
+
+def f2[T: int](x: T) -> T:
+    return x
+
+i: int = f2(True)
+reveal_type(i)  # revealed: int
+
+j: int | str = f2(True)
+reveal_type(j)  # revealed: Literal[True]
+```
diff --git a/crates/ty_python_semantic/src/types.rs b/crates/ty_python_semantic/src/types.rs
index bf68255901..57b403b307 100644
--- a/crates/ty_python_semantic/src/types.rs
+++ b/crates/ty_python_semantic/src/types.rs
@@ -4805,7 +4805,7 @@ impl<'db> Type<'db> {
     ) -> Result<Bindings<'db>, CallError<'db>> {
         self.bindings(db)
             .match_parameters(db, argument_types)
-            .check_types(db, argument_types)
+            .check_types(db, argument_types, &TypeContext::default())
     }
 
     /// Look up a dunder method on the meta-type of `self` and call it.
@@ -4854,7 +4854,7 @@ impl<'db> Type<'db> {
                 let bindings = dunder_callable
                     .bindings(db)
                     .match_parameters(db, argument_types)
-                    .check_types(db, argument_types)?;
+                    .check_types(db, argument_types, &TypeContext::default())?;
                 if boundness == Boundness::PossiblyUnbound {
                     return Err(CallDunderError::PossiblyUnbound(Box::new(bindings)));
                 }
diff --git a/crates/ty_python_semantic/src/types/call/bind.rs b/crates/ty_python_semantic/src/types/call/bind.rs
index c1da805d48..e19e1c6c04 100644
--- a/crates/ty_python_semantic/src/types/call/bind.rs
+++ b/crates/ty_python_semantic/src/types/call/bind.rs
@@ -32,8 +32,8 @@ use crate::types::tuple::{TupleLength, TupleType};
 use crate::types::{
     BoundMethodType, ClassLiteral, DataclassParams, FieldInstance, KnownBoundMethodType,
     KnownClass, KnownInstanceType, MemberLookupPolicy, PropertyInstanceType, SpecialFormType,
-    TrackedConstraintSet, TypeAliasType, TypeMapping, UnionType, WrapperDescriptorKind, enums,
-    ide_support, todo_type,
+    TrackedConstraintSet, TypeAliasType, TypeContext, TypeMapping, UnionType,
+    WrapperDescriptorKind, enums, ide_support, todo_type,
 };
 use ruff_db::diagnostic::{Annotation, Diagnostic, SubDiagnostic, SubDiagnosticSeverity};
 use ruff_python_ast::{self as ast, PythonVersion};
@@ -122,6 +122,9 @@ impl<'db> Bindings<'db> {
     /// You must provide an `argument_types` that was created from the same `arguments` that you
     /// provided to [`match_parameters`][Self::match_parameters].
     ///
+    /// The type context of the call expression is also used to infer the specialization of generic
+    /// calls.
+    ///
     /// We update the bindings to include the return type of the call, the bound types for all
     /// parameters, and any errors resulting from binding the call, all for each union element and
     /// overload (if any).
@@ -129,9 +132,12 @@ impl<'db> Bindings<'db> {
         mut self,
         db: &'db dyn Db,
         argument_types: &CallArguments<'_, 'db>,
+        call_expression_tcx: &TypeContext<'db>,
     ) -> Result<Self, CallError<'db>> {
         for element in &mut self.elements {
-            if let Some(mut updated_argument_forms) = element.check_types(db, argument_types) {
+            if let Some(mut updated_argument_forms) =
+                element.check_types(db, argument_types, call_expression_tcx)
+            {
                 // If this element returned a new set of argument forms (indicating successful
                 // argument type expansion), update the `Bindings` with these forms.
                 updated_argument_forms.shrink_to_fit();
@@ -1281,6 +1287,7 @@ impl<'db> CallableBinding<'db> {
         &mut self,
         db: &'db dyn Db,
         argument_types: &CallArguments<'_, 'db>,
+        call_expression_tcx: &TypeContext<'db>,
     ) -> Option<ArgumentForms> {
         // If this callable is a bound method, prepend the self instance onto the arguments list
         // before checking.
@@ -1293,7 +1300,7 @@ impl<'db> CallableBinding<'db> {
                 // still perform type checking for non-overloaded function to provide better user
                 // experience.
                 if let [overload] = self.overloads.as_mut_slice() {
-                    overload.check_types(db, argument_types.as_ref());
+                    overload.check_types(db, argument_types.as_ref(), call_expression_tcx);
                 }
                 return None;
             }
@@ -1301,7 +1308,7 @@ impl<'db> CallableBinding<'db> {
                 // If only one candidate overload remains, it is the winning match. Evaluate it as
                 // a regular (non-overloaded) call.
                 self.matching_overload_index = Some(index);
-                self.overloads[index].check_types(db, argument_types.as_ref());
+                self.overloads[index].check_types(db, argument_types.as_ref(), call_expression_tcx);
                 return None;
             }
             MatchingOverloadIndex::Multiple(indexes) => {
@@ -1313,7 +1320,7 @@ impl<'db> CallableBinding<'db> {
         // Step 2: Evaluate each remaining overload as a regular (non-overloaded) call to determine
         // whether it is compatible with the supplied argument list.
         for (_, overload) in self.matching_overloads_mut() {
-            overload.check_types(db, argument_types.as_ref());
+            overload.check_types(db, argument_types.as_ref(), call_expression_tcx);
         }
 
         match self.matching_overload_index() {
@@ -1430,7 +1437,7 @@ impl<'db> CallableBinding<'db> {
                 merged_argument_forms.merge(&argument_forms);
 
                 for (_, overload) in self.matching_overloads_mut() {
-                    overload.check_types(db, expanded_arguments);
+                    overload.check_types(db, expanded_arguments, call_expression_tcx);
                 }
 
                 let return_type = match self.matching_overload_index() {
@@ -2243,6 +2250,7 @@ struct ArgumentTypeChecker<'a, 'db> {
     arguments: &'a CallArguments<'a, 'db>,
     argument_matches: &'a [MatchedArgument<'db>],
     parameter_tys: &'a mut [Option<Type<'db>>],
+    call_expression_tcx: &'a TypeContext<'db>,
     errors: &'a mut Vec<BindingError<'db>>,
 
     specialization: Option<Specialization<'db>>,
@@ -2256,6 +2264,7 @@ impl<'a, 'db> ArgumentTypeChecker<'a, 'db> {
         arguments: &'a CallArguments<'a, 'db>,
         argument_matches: &'a [MatchedArgument<'db>],
         parameter_tys: &'a mut [Option<Type<'db>>],
+        call_expression_tcx: &'a TypeContext<'db>,
         errors: &'a mut Vec<BindingError<'db>>,
     ) -> Self {
         Self {
@@ -2264,6 +2273,7 @@ impl<'a, 'db> ArgumentTypeChecker<'a, 'db> {
             arguments,
             argument_matches,
             parameter_tys,
+            call_expression_tcx,
             errors,
             specialization: None,
             inherited_specialization: None,
@@ -2304,8 +2314,20 @@ impl<'a, 'db> ArgumentTypeChecker<'a, 'db> {
             return;
         }
 
-        let parameters = self.signature.parameters();
         let mut builder = SpecializationBuilder::new(self.db);
+
+        // Note that we infer the annotated type _before_ the arguments if this call is part of
+        // an annotated assignment, to closer match the order of any unions written in the type
+        // annotation.
+        if let Some(return_ty) = self.signature.return_ty
+            && let Some(call_expression_tcx) = self.call_expression_tcx.annotation
+        {
+            // Ignore any specialization errors here, because the type context is only used to
+            // optionally widen the return type.
+            let _ = builder.infer(return_ty, call_expression_tcx);
+        }
+
+        let parameters = self.signature.parameters();
         for (argument_index, adjusted_argument_index, _, argument_type) in
             self.enumerate_argument_types()
         {
@@ -2316,6 +2338,7 @@ impl<'a, 'db> ArgumentTypeChecker<'a, 'db> {
                 let Some(expected_type) = parameter.annotated_type() else {
                     continue;
                 };
+
                 if let Err(error) = builder.infer(
                     expected_type,
                     variadic_argument_type.unwrap_or(argument_type),
@@ -2327,6 +2350,7 @@ impl<'a, 'db> ArgumentTypeChecker<'a, 'db> {
                 }
             }
         }
+
         self.specialization = self.signature.generic_context.map(|gc| builder.build(gc));
         self.inherited_specialization = self.signature.inherited_generic_context.map(|gc| {
             // The inherited generic context is used when inferring the specialization of a generic
@@ -2688,13 +2712,19 @@ impl<'db> Binding<'db> {
         self.argument_matches = matcher.finish();
     }
 
-    fn check_types(&mut self, db: &'db dyn Db, arguments: &CallArguments<'_, 'db>) {
+    fn check_types(
+        &mut self,
+        db: &'db dyn Db,
+        arguments: &CallArguments<'_, 'db>,
+        call_expression_tcx: &TypeContext<'db>,
+    ) {
         let mut checker = ArgumentTypeChecker::new(
             db,
             &self.signature,
             arguments,
             &self.argument_matches,
             &mut self.parameter_tys,
+            call_expression_tcx,
             &mut self.errors,
         );
 
diff --git a/crates/ty_python_semantic/src/types/infer.rs b/crates/ty_python_semantic/src/types/infer.rs
index 7f81248a22..cbeef15ab9 100644
--- a/crates/ty_python_semantic/src/types/infer.rs
+++ b/crates/ty_python_semantic/src/types/infer.rs
@@ -352,7 +352,7 @@ struct ExpressionWithContext<'db> {
 /// more precise inference results, aka "bidirectional type inference".
 #[derive(Default, Copy, Clone, Debug, PartialEq, Eq, Hash, get_size2::GetSize)]
 pub(crate) struct TypeContext<'db> {
-    annotation: Option<Type<'db>>,
+    pub(crate) annotation: Option<Type<'db>>,
 }
 
 impl<'db> TypeContext<'db> {
diff --git a/crates/ty_python_semantic/src/types/infer/builder.rs b/crates/ty_python_semantic/src/types/infer/builder.rs
index ad774d38ea..c5cf398c24 100644
--- a/crates/ty_python_semantic/src/types/infer/builder.rs
+++ b/crates/ty_python_semantic/src/types/infer/builder.rs
@@ -5775,7 +5775,7 @@ impl<'db, 'ast> TypeInferenceBuilder<'db, 'ast> {
     fn infer_call_expression(
         &mut self,
         call_expression: &ast::ExprCall,
-        _tcx: TypeContext<'db>,
+        tcx: TypeContext<'db>,
     ) -> Type<'db> {
         let ast::ExprCall {
             range: _,
@@ -5955,7 +5955,7 @@ impl<'db, 'ast> TypeInferenceBuilder<'db, 'ast> {
             }
         }
 
-        let mut bindings = match bindings.check_types(self.db(), &call_arguments) {
+        let mut bindings = match bindings.check_types(self.db(), &call_arguments, &tcx) {
             Ok(bindings) => bindings,
             Err(CallError(_, bindings)) => {
                 bindings.report_diagnostics(&self.context, call_expression.into());
@@ -8521,7 +8521,7 @@ impl<'db, 'ast> TypeInferenceBuilder<'db, 'ast> {
         let binding = Binding::single(value_ty, generic_context.signature(self.db()));
         let bindings = match Bindings::from(binding)
             .match_parameters(self.db(), &call_argument_types)
-            .check_types(self.db(), &call_argument_types)
+            .check_types(self.db(), &call_argument_types, &TypeContext::default())
         {
             Ok(bindings) => bindings,
             Err(CallError(_, bindings)) => {