diff --git a/crates/ty_python_semantic/src/module_resolver/module.rs b/crates/ty_python_semantic/src/module_resolver/module.rs
index 7d61e65818..67a2f4eff5 100644
--- a/crates/ty_python_semantic/src/module_resolver/module.rs
+++ b/crates/ty_python_semantic/src/module_resolver/module.rs
@@ -330,6 +330,8 @@ pub enum KnownModule {
     UnittestMock,
     #[cfg(test)]
     Uuid,
+    #[cfg(test)]
+    UnderscoreSsl,
     Warnings,
 }
 
@@ -355,6 +357,8 @@ impl KnownModule {
             Self::UnittestMock => "unittest.mock",
             #[cfg(test)]
             Self::Uuid => "uuid",
+            #[cfg(test)]
+            Self::UnderscoreSsl => "_ssl",
             Self::Templatelib => "string.templatelib",
         }
     }
diff --git a/crates/ty_python_semantic/src/types.rs b/crates/ty_python_semantic/src/types.rs
index ece4c38ab1..0029fe2fde 100644
--- a/crates/ty_python_semantic/src/types.rs
+++ b/crates/ty_python_semantic/src/types.rs
@@ -1460,11 +1460,6 @@ impl<'db> Type<'db> {
                     .has_relation_to_impl(db, right, relation, visitor)
             }
 
-            (Type::TypedDict(_), _) | (_, Type::TypedDict(_)) => {
-                // TODO: Implement assignability and subtyping for TypedDict
-                C::from_bool(db, relation.is_assignability())
-            }
-
             // In general, a TypeVar `T` is not a subtype of a type `S` unless one of the two conditions is satisfied:
             // 1. `T` is a bound TypeVar and `T`'s upper bound is a subtype of `S`.
             //    TypeVars without an explicit upper bound are treated as having an implicit upper bound of `object`.
@@ -1816,6 +1811,16 @@ impl<'db> Type<'db> {
                 .unwrap_or_else(|| KnownClass::Type.to_instance(db))
                 .has_relation_to_impl(db, target, relation, visitor),
 
+            (Type::TypedDict(left), Type::TypedDict(right)) if left == right => {
+                // TODO: Implement structural assignability and subtyping for TypedDict
+                C::always_satisfiable(db)
+            }
+
+            (Type::TypedDict(_), _) | (_, Type::TypedDict(_)) => {
+                // TODO: Implement structural assignability and subtyping for TypedDict
+                C::from_bool(db, relation.is_assignability())
+            }
+
             // For example: `Type::SpecialForm(SpecialFormType::Type)` is a subtype of `Type::NominalInstance(_SpecialForm)`,
             // because `Type::SpecialForm(SpecialFormType::Type)` is a set with exactly one runtime value in it
             // (the symbol `typing.Type`), and that symbol is known to be an instance of `typing._SpecialForm` at runtime.
diff --git a/crates/ty_python_semantic/src/types/property_tests/type_generation.rs b/crates/ty_python_semantic/src/types/property_tests/type_generation.rs
index 0a296088ff..3da9ce703e 100644
--- a/crates/ty_python_semantic/src/types/property_tests/type_generation.rs
+++ b/crates/ty_python_semantic/src/types/property_tests/type_generation.rs
@@ -64,6 +64,8 @@ pub(crate) enum Ty {
     /// where the class has `Any` in its MRO
     UnittestMockInstance,
     UnittestMockLiteral,
+    /// A custom `TypedDict`, imported from the `_ssl` module
+    TypedDict(&'static str),
 }
 
 #[derive(Debug, Clone, PartialEq)]
@@ -236,6 +238,15 @@ impl Ty {
                     returns.map(|ty| ty.into_type(db)),
                 ),
             ),
+            Ty::TypedDict(name) => {
+                let ty = known_module_symbol(db, KnownModule::UnderscoreSsl, name)
+                    .place
+                    .expect_type()
+                    .to_instance(db)
+                    .expect("Class type should be convertible to instance");
+                assert!(ty.is_typed_dict());
+                ty
+            }
         }
     }
 }
@@ -314,6 +325,8 @@ fn arbitrary_core_type(g: &mut Gen, fully_static: bool) -> Ty {
             class: "int",
             method: "bit_length",
         },
+        Ty::TypedDict("_Cipher"),
+        Ty::TypedDict("_CertInfo"),
     ];
     let types = if fully_static {
         &types[fully_static_index..]