diff --git a/crates/ty_python_semantic/resources/mdtest/assignment/annotations.md b/crates/ty_python_semantic/resources/mdtest/assignment/annotations.md
index d95cc52fd1..6573b001af 100644
--- a/crates/ty_python_semantic/resources/mdtest/assignment/annotations.md
+++ b/crates/ty_python_semantic/resources/mdtest/assignment/annotations.md
@@ -402,40 +402,48 @@ python-version = "3.12"
 `generic_list.py`:
 
 ```py
-from typing import Literal
+from typing import Literal, Sequence
 
 def f[T](x: T) -> list[T]:
     return [x]
 
-a = f("a")
-reveal_type(a)  # revealed: list[str]
+x1 = f("a")
+reveal_type(x1)  # revealed: list[str]
 
-b: list[int | Literal["a"]] = f("a")
-reveal_type(b)  # revealed: list[int | Literal["a"]]
+x2: list[int | Literal["a"]] = f("a")
+reveal_type(x2)  # revealed: list[int | Literal["a"]]
 
-c: list[int | str] = f("a")
-reveal_type(c)  # revealed: list[int | str]
+x3: list[int | str] = f("a")
+reveal_type(x3)  # revealed: list[int | str]
 
-d: list[int | tuple[int, int]] = f((1, 2))
-reveal_type(d)  # revealed: list[int | tuple[int, int]]
+x4: list[int | tuple[int, int]] = f((1, 2))
+reveal_type(x4)  # revealed: list[int | tuple[int, int]]
 
-e: list[int] = f(True)
-reveal_type(e)  # revealed: list[int]
+x5: list[int] = f(True)
+reveal_type(x5)  # revealed: list[int]
 
 # error: [invalid-assignment] "Object of type `list[int | str]` is not assignable to `list[int]`"
-g: list[int] = f("a")
+x6: list[int] = f("a")
 
 # error: [invalid-assignment] "Object of type `list[str]` is not assignable to `tuple[int]`"
-h: tuple[int] = f("a")
+x7: tuple[int] = f("a")
 
 def f2[T: int](x: T) -> T:
     return x
 
-i: int = f2(True)
-reveal_type(i)  # revealed: Literal[True]
+x8: int = f2(True)
+reveal_type(x8)  # revealed: Literal[True]
 
-j: int | str = f2(True)
-reveal_type(j)  # revealed: Literal[True]
+x9: int | str = f2(True)
+reveal_type(x9)  # revealed: Literal[True]
+
+# TODO: We could choose a concrete type here.
+x10: list[int | str] | list[int | None] = [1, 2, 3]
+reveal_type(x10)  # revealed: list[Unknown | int]
+
+# TODO: And here similarly.
+x11: Sequence[int | str] | Sequence[int | None] = [1, 2, 3]
+reveal_type(x11)  # revealed: list[Unknown | int]
 ```
 
 A function's arguments are also inferred using the type context:
diff --git a/crates/ty_python_semantic/src/types/generics.rs b/crates/ty_python_semantic/src/types/generics.rs
index 13725d9358..5173dfee6e 100644
--- a/crates/ty_python_semantic/src/types/generics.rs
+++ b/crates/ty_python_semantic/src/types/generics.rs
@@ -1872,8 +1872,8 @@ impl<'db> SpecializationBuilder<'db> {
         Ok(())
     }
 
-    /// Infer type mappings for the specialization in the reverse direction, i.e., where the given type contains
-    /// inferable type variables.
+    /// Infer type mappings for the specialization in the reverse direction, i.e., where the given type, not the
+    /// declared type, contains inferable type variables.
     pub(crate) fn infer_reverse(
         &mut self,
         formal: Type<'db>,
@@ -1885,7 +1885,7 @@ impl<'db> SpecializationBuilder<'db> {
             TypeContext::default(),
         );
 
-        // Collect all type variables on the actual type.
+        // Collect any type variables on the formal type.
         let mut formal_type_vars = Vec::new();
         formal.visit_specialization(self.db, TypeContext::default(), |typevar, _, _, _| {
             formal_type_vars.push(typevar);
diff --git a/crates/ty_python_semantic/src/types/infer/builder.rs b/crates/ty_python_semantic/src/types/infer/builder.rs
index dec104afb0..7d7bfc1764 100644
--- a/crates/ty_python_semantic/src/types/infer/builder.rs
+++ b/crates/ty_python_semantic/src/types/infer/builder.rs
@@ -7738,7 +7738,14 @@ impl<'db, 'ast> TypeInferenceBuilder<'db, 'ast> {
                 generic_context.inferable_typevars(self.db()),
             );
 
-            if let Some(tcx) = tcx.annotation {
+            if let Some(tcx) = tcx.annotation
+                // If there are multiple potential type contexts, we fallback to `Unknown`.
+                // TODO: We could perform multi-inference here.
+                && tcx
+                    .filter_union(self.db(), |ty| ty.class_specialization(self.db()).is_some())
+                    .class_specialization(self.db())
+                    .is_some()
+            {
                 let collection_instance =
                     Type::instance(self.db(), ClassType::Generic(collection_alias));
                 builder.infer_reverse(tcx, collection_instance).ok()?;