diff --git a/Lib/annotationlib.py b/Lib/annotationlib.py
index c41df197eee7d5e..2be779a5f18b62c 100644
--- a/Lib/annotationlib.py
+++ b/Lib/annotationlib.py
@@ -6,6 +6,7 @@
 import keyword
 import sys
 import types
+lazy import typing
 
 __all__ = [
     "Format",
@@ -410,6 +411,48 @@ def __convert_to_ast(self, other):
                 elts.append(new_elt)
             ast_class = {list: ast.List, tuple: ast.Tuple, set: ast.Set}[type(other)]
             return ast_class(elts), extra_names
+        elif type(other) is types.GenericAlias or _is_annotated_alias(other):
+            if _is_annotated_alias(other):
+                annotated_alias = True
+                origin = typing.get_origin(other)
+                args = typing.get_args(other)
+            else:
+                annotated_alias = False
+                origin = other.__origin__
+                args = other.__args__
+
+            extra_names = {}
+            elts = []
+
+            origin_ast, origin_names = self.__convert_to_ast(origin)
+            if origin_names is not None:
+                extra_names |= origin_names
+
+            for elt in args:
+                new_elt, new_extra_names = self.__convert_to_ast(elt)
+                if new_extra_names is not None:
+                    extra_names |= new_extra_names
+                elts.append(new_elt)
+
+            if len(elts) == 1:
+                elts = elts[0]
+            else:
+                elts = ast.Tuple(elts=elts)
+
+            if annotated_alias:
+                new_ast = ast.Subscript(
+                    value=origin_ast,
+                    slice=elts,
+                )
+            else:
+                # Generic Alias is not guaranteed to be from subscript
+                alias_ast, alias_names = self.__convert_to_ast(types.GenericAlias)
+                extra_names |= alias_names
+                new_ast = ast.Call(
+                    func=alias_ast,
+                    args=[origin_ast, elts],
+                )
+            return new_ast, extra_names
         else:
             name = self.__stringifier_dict__.create_unique_name()
             return ast.Name(id=name), {name: other}
@@ -1191,7 +1234,30 @@ class _ExtraNameFixer(ast.NodeTransformer):
     def __init__(self, extra_names):
         self.extra_names = extra_names
 
+    def visit_Call(self, node: ast.Call):
+        # Convert calls to `GenericAlias` to their string representation
+        if (
+            isinstance((func := node.func), ast.Name)
+            and self.extra_names.get(func.id) is types.GenericAlias
+        ):
+            new_node = ast.Subscript(
+                value=node.args[0],
+                slice=node.args[1],
+            )
+            self.generic_visit(new_node)
+            return new_node
+
+        self.generic_visit(node)
+        return node
+
     def visit_Name(self, node: ast.Name):
         if (new_name := self.extra_names.get(node.id, _sentinel)) is not _sentinel:
             node = ast.Name(id=type_repr(new_name))
         return node
+
+
+def _is_annotated_alias(obj):
+    return (
+        (typing := sys.modules.get("typing"))
+        and typing.get_origin(obj) is typing.Annotated
+    )
diff --git a/Lib/test/test_annotationlib.py b/Lib/test/test_annotationlib.py
index 56e5731849cbd7c..522dd7a660293de 100644
--- a/Lib/test/test_annotationlib.py
+++ b/Lib/test/test_annotationlib.py
@@ -237,6 +237,99 @@ class UnionForwardrefs:
             arg2, support.EqualToForwardRef("undefined", is_class=True, owner=UnionForwardrefs)
         )
 
+    def test_nested_deferred(self):
+        # Test that ForwardReferences inside generic aliases and
+        # typing.Annotated are correctly caught and resolved.
+
+        class NestedForwardRefs:
+            genericalias: Unknown1[str, list[Unknown2]]
+            annotated: Unknown1[str, typing.Annotated[Unknown2, '']]
+            extra_nested: Unknown3[tuple[Unknown4[list[Unknown5]]]]
+
+        annos = get_annotations(NestedForwardRefs, format=Format.FORWARDREF)
+
+        gen = annos['genericalias']
+        annotated = annos['annotated']
+        nested = annos['extra_nested']
+
+        self.assertEqual(
+            gen.evaluate(format=Format.STRING),
+            "Unknown1[str, list[Unknown2]]"
+        )
+
+        self.assertEqual(
+            annotated.evaluate(format=Format.STRING),
+            "Unknown1[str, typing.Annotated[Unknown2, '']]",
+        )
+
+        self.assertEqual(
+            nested.evaluate(format=Format.STRING),
+            "Unknown3[tuple[Unknown4[list[Unknown5]]]]",
+        )
+
+        Unknown1 = tuple
+        # Unknown2 is still undefined, these should raise
+        with self.assertRaises(NameError):
+            gen.evaluate()
+        with self.assertRaises(NameError):
+            annotated.evaluate()
+
+        # Test that the annotations fully evaluate now both unknowns are defined
+        Unknown2 = str
+        self.assertEqual(
+            gen.evaluate(),
+            tuple[str, list[str]],
+        )
+
+        self.assertEqual(
+            annotated.evaluate(),
+            tuple[str, typing.Annotated[str, '']],
+        )
+
+        Unknown3 = list
+        Unknown4 = set
+        Unknown5 = int
+        self.assertEqual(
+            nested.evaluate(),
+            list[tuple[set[list[int]]]],
+        )
+
+    def test_nested_special_generic(self):
+        # Test that ForwardRef works correctly for generic aliases that aren't
+        # created through subscripting
+        class NonSubscriptableGeneric:
+            @classmethod
+            def get_generic(cls, *args):
+                return types.GenericAlias(cls, args)
+
+        nsrepr = type_repr(NonSubscriptableGeneric)
+
+        with self.assertRaises(TypeError):
+            _ = NonSubscriptableGeneric[str]
+
+        class C:
+            x: Unknown1[NonSubscriptableGeneric.get_generic(str, Unknown2)]
+
+        ann = get_annotations(C, format=Format.FORWARDREF)['x']
+
+        Unknown1 = list
+
+        with self.assertRaises(NameError):
+            ann.evaluate()
+
+        Unknown2 = int
+
+        self.assertEqual(
+            ann.evaluate(),
+            list[NonSubscriptableGeneric.get_generic(str, int)],
+        )
+
+        # The string representation should look like the __repr__ for GenericAlias
+        self.assertEqual(
+            ann.evaluate(format=Format.STRING),
+            f"Unknown1[{nsrepr}[str, Unknown2]]",
+        )
+
 
 class TestStringFormat(unittest.TestCase):
     def test_closure(self):
diff --git a/Misc/NEWS.d/next/Library/2026-10-28-10-57-05.gh-issue-160766.wqI7qo.rst b/Misc/NEWS.d/next/Library/2026-10-28-10-57-05.gh-issue-160766.wqI7qo.rst
new file mode 100644
index 000000000000000..df2d0db2ec8cf7a
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2026-10-28-10-57-05.gh-issue-160766.wqI7qo.rst
@@ -0,0 +1 @@
+Fix :mod:`annotationlib` forward references inside a :class:`types.GenericAlias` or :class:`typing.Annotated` inside an outer :class:`annotationlib.ForwardRef` no longer evade evaluation.