diff --git a/.release-please-manifest.json b/.release-please-manifest.json
index 934f2cc0..396d9f01 100644
--- a/.release-please-manifest.json
+++ b/.release-please-manifest.json
@@ -1,3 +1,3 @@
 {
-  ".": "4.4.0"
+  ".": "4.4.1"
 }
\ No newline at end of file
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2ac37aa9..1023877d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,19 @@
 # Changelog
 
+## 4.4.1 (2025-07-09)
+
+Full Changelog: [v4.4.0...v4.4.1](https://github.com/orbcorp/orb-python/compare/v4.4.0...v4.4.1)
+
+### Bug Fixes
+
+* **parsing:** correctly handle nested discriminated unions ([7911534](https://github.com/orbcorp/orb-python/commit/791153479d7474d601721dee8f6d3776738fb166))
+
+
+### Chores
+
+* **internal:** bump pinned h11 dep ([efc47f2](https://github.com/orbcorp/orb-python/commit/efc47f2b2d20840cbef95824091cd2d5a9676dbf))
+* **package:** mark python 3.13 as supported ([21d5e3b](https://github.com/orbcorp/orb-python/commit/21d5e3b4494b542d1b72ff9deab08d6736c349e1))
+
 ## 4.4.0 (2025-07-08)
 
 Full Changelog: [v4.3.0...v4.4.0](https://github.com/orbcorp/orb-python/compare/v4.3.0...v4.4.0)
diff --git a/pyproject.toml b/pyproject.toml
index ad83c6ec..8db80a9f 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -1,6 +1,6 @@
 [project]
 name = "orb-billing"
-version = "4.4.0"
+version = "4.4.1"
 description = "The official Python library for the orb API"
 dynamic = ["readme"]
 license = "Apache-2.0"
@@ -24,6 +24,7 @@ classifiers = [
   "Programming Language :: Python :: 3.10",
   "Programming Language :: Python :: 3.11",
   "Programming Language :: Python :: 3.12",
+  "Programming Language :: Python :: 3.13",
   "Operating System :: OS Independent",
   "Operating System :: POSIX",
   "Operating System :: MacOS",
diff --git a/requirements-dev.lock b/requirements-dev.lock
index ddc24491..1fef201f 100644
--- a/requirements-dev.lock
+++ b/requirements-dev.lock
@@ -48,9 +48,9 @@ filelock==3.12.4
 frozenlist==1.6.2
     # via aiohttp
     # via aiosignal
-h11==0.14.0
+h11==0.16.0
     # via httpcore
-httpcore==1.0.2
+httpcore==1.0.9
     # via httpx
 httpx==0.28.1
     # via httpx-aiohttp
diff --git a/requirements.lock b/requirements.lock
index b091c4df..89eca7e0 100644
--- a/requirements.lock
+++ b/requirements.lock
@@ -36,9 +36,9 @@ exceptiongroup==1.2.2
 frozenlist==1.6.2
     # via aiohttp
     # via aiosignal
-h11==0.14.0
+h11==0.16.0
     # via httpcore
-httpcore==1.0.2
+httpcore==1.0.9
     # via httpx
 httpx==0.28.1
     # via httpx-aiohttp
diff --git a/src/orb/_models.py b/src/orb/_models.py
index 4f214980..528d5680 100644
--- a/src/orb/_models.py
+++ b/src/orb/_models.py
@@ -2,9 +2,10 @@
 
 import os
 import inspect
-from typing import TYPE_CHECKING, Any, Type, Union, Generic, TypeVar, Callable, cast
+from typing import TYPE_CHECKING, Any, Type, Union, Generic, TypeVar, Callable, Optional, cast
 from datetime import date, datetime
 from typing_extensions import (
+    List,
     Unpack,
     Literal,
     ClassVar,
@@ -366,7 +367,7 @@ def _construct_field(value: object, field: FieldInfo, key: str) -> object:
     if type_ is None:
         raise RuntimeError(f"Unexpected field type is None for {key}")
 
-    return construct_type(value=value, type_=type_)
+    return construct_type(value=value, type_=type_, metadata=getattr(field, "metadata", None))
 
 
 def is_basemodel(type_: type) -> bool:
@@ -420,7 +421,7 @@ def construct_type_unchecked(*, value: object, type_: type[_T]) -> _T:
     return cast(_T, construct_type(value=value, type_=type_))
 
 
-def construct_type(*, value: object, type_: object) -> object:
+def construct_type(*, value: object, type_: object, metadata: Optional[List[Any]] = None) -> object:
     """Loose coercion to the expected type with construction of nested values.
 
     If the given value does not match the expected type then it is returned as-is.
@@ -438,8 +439,10 @@ def construct_type(*, value: object, type_: object) -> object:
         type_ = type_.__value__  # type: ignore[unreachable]
 
     # unwrap `Annotated[T, ...]` -> `T`
-    if is_annotated_type(type_):
-        meta: tuple[Any, ...] = get_args(type_)[1:]
+    if metadata is not None:
+        meta: tuple[Any, ...] = tuple(metadata)
+    elif is_annotated_type(type_):
+        meta = get_args(type_)[1:]
         type_ = extract_type_arg(type_, 0)
     else:
         meta = tuple()
diff --git a/src/orb/_version.py b/src/orb/_version.py
index 020943ea..0c52e5ff 100644
--- a/src/orb/_version.py
+++ b/src/orb/_version.py
@@ -1,4 +1,4 @@
 # File generated from our OpenAPI spec by Stainless. See CONTRIBUTING.md for details.
 
 __title__ = "orb"
-__version__ = "4.4.0"  # x-release-please-version
+__version__ = "4.4.1"  # x-release-please-version
diff --git a/tests/test_models.py b/tests/test_models.py
index 682b85ca..6a744074 100644
--- a/tests/test_models.py
+++ b/tests/test_models.py
@@ -889,3 +889,48 @@ class ModelB(BaseModel):
     )
 
     assert isinstance(m, ModelB)
+
+
+def test_nested_discriminated_union() -> None:
+    class InnerType1(BaseModel):
+        type: Literal["type_1"]
+
+    class InnerModel(BaseModel):
+        inner_value: str
+
+    class InnerType2(BaseModel):
+        type: Literal["type_2"]
+        some_inner_model: InnerModel
+
+    class Type1(BaseModel):
+        base_type: Literal["base_type_1"]
+        value: Annotated[
+            Union[
+                InnerType1,
+                InnerType2,
+            ],
+            PropertyInfo(discriminator="type"),
+        ]
+
+    class Type2(BaseModel):
+        base_type: Literal["base_type_2"]
+
+    T = Annotated[
+        Union[
+            Type1,
+            Type2,
+        ],
+        PropertyInfo(discriminator="base_type"),
+    ]
+
+    model = construct_type(
+        type_=T,
+        value={
+            "base_type": "base_type_1",
+            "value": {
+                "type": "type_2",
+            },
+        },
+    )
+    assert isinstance(model, Type1)
+    assert isinstance(model.value, InnerType2)