diff --git a/CHANGELOG.md b/CHANGELOG.md
index bdbe3927..70ac198b 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -16,6 +16,9 @@ Types of changes
 
 # Latch SDK Changelog
 
+## 2.76.5 - 2026-06-22
+
+* Fix LatchFilePathTransformer for Annotated types
 
 ## 2.76.3 - 2026-06-19
 
diff --git a/pyproject.toml b/pyproject.toml
index 52592617..2acc7ee7 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -12,7 +12,7 @@ include = ["src/**/*.py", "src/**/*.graphql", "src/**/py.typed", "src/latch_cli/
 
 [project]
 name = "latch"
-version = "2.76.4"
+version = "2.76.5"
 description = "The Latch SDK"
 authors = [{ name = "Kenny Workman", email = "kenny@latch.bio" }]
 maintainers = [{ name = "Kenny Workman", email = "kenny@latch.bio" }]
diff --git a/src/latch/types/file.py b/src/latch/types/file.py
index 25d2de6a..5b248993 100644
--- a/src/latch/types/file.py
+++ b/src/latch/types/file.py
@@ -1,7 +1,7 @@
 import os
 from os import PathLike
 from pathlib import Path
-from typing import Annotated, Optional, Union
+from typing import Annotated, Optional, Union, get_args, get_origin
 from urllib.parse import urlparse
 
 import gql
@@ -249,6 +249,9 @@ def to_python_value(
                 "Casting from Pathlike to LatchFile is currently not supported."
             )
 
+        while get_origin(expected_python_type) == Annotated:
+            expected_python_type = get_args(expected_python_type)[0]
+
         if not issubclass(expected_python_type, LatchFile):
             raise TypeError(
                 f"Neither os.PathLike nor LatchFile specified {expected_python_type}"
diff --git a/uv.lock b/uv.lock
index 0de0cb5d..186c9216 100644
--- a/uv.lock
+++ b/uv.lock
@@ -1255,7 +1255,7 @@ wheels = [
 
 [[package]]
 name = "latch"
-version = "2.76.3"
+version = "2.76.5"
 source = { editable = "." }
 dependencies = [
     { name = "apscheduler" },