diff --git a/.release-please-manifest.json b/.release-please-manifest.json
index 5d9bde2..0bb2e42 100644
--- a/.release-please-manifest.json
+++ b/.release-please-manifest.json
@@ -1,3 +1,3 @@
 {
-  ".": "3.37.0"
+  ".": "3.38.0"
 }
\ No newline at end of file
diff --git a/.stats.yml b/.stats.yml
index 561f9fe..485cf29 100644
--- a/.stats.yml
+++ b/.stats.yml
@@ -1,4 +1,4 @@
 configured_endpoints: 26
-openapi_spec_url: https://storage.googleapis.com/stainless-sdk-openapi-specs/supermemory--inc%2Fsupermemory-new-f979eba02e9720ab41111944b4f4441caf9b3f0c56e1d85ac4ddd4a2b0fa7ede.yml
-openapi_spec_hash: aacf6838b9ec2431611e87fab118d913
+openapi_spec_url: https://storage.googleapis.com/stainless-sdk-openapi-specs/supermemory--inc/supermemory-new-5e1ac142b427e15ca46d0920c4d65c6e1f464e46ce014e42cd5a716f97b820ab.yml
+openapi_spec_hash: f0d9f62796cf1fb5dd79dad7b1c692fd
 config_hash: cde97ef3188581c5f4924c633ec33ddb
diff --git a/CHANGELOG.md b/CHANGELOG.md
index ad5c9f8..bad0e98 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,18 @@
 # Changelog
 
+## 3.38.0 (2026-05-08)
+
+Full Changelog: [v3.37.0...v3.38.0](https://github.com/supermemoryai/python-sdk/compare/v3.37.0...v3.38.0)
+
+### Features
+
+* **api:** api update ([25be280](https://github.com/supermemoryai/python-sdk/commit/25be280240889b7ecadc3727aabdf85d614f38ec))
+
+
+### Chores
+
+* **internal:** reformat pyproject.toml ([1d58848](https://github.com/supermemoryai/python-sdk/commit/1d58848385ad806699a3c4ef6d40dd606e27f8b1))
+
 ## 3.37.0 (2026-04-28)
 
 Full Changelog: [v3.36.0...v3.37.0](https://github.com/supermemoryai/python-sdk/compare/v3.36.0...v3.37.0)
diff --git a/pyproject.toml b/pyproject.toml
index 478e8bf..3de4295 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -1,6 +1,6 @@
 [project]
 name = "supermemory"
-version = "3.37.0"
+version = "3.38.0"
 description = "The official Python library for the supermemory API"
 dynamic = ["readme"]
 license = "Apache-2.0"
@@ -168,7 +168,7 @@ show_error_codes = true
 #
 # We also exclude our `tests` as mypy doesn't always infer
 # types correctly and Pyright will still catch any type errors.
-exclude = ['src/supermemory/_files.py', '_dev/.*.py', 'tests/.*']
+exclude = ["src/supermemory/_files.py", "_dev/.*.py", "tests/.*"]
 
 strict_equality = true
 implicit_reexport = true
diff --git a/src/supermemory/_version.py b/src/supermemory/_version.py
index ce33f78..15c5a2a 100644
--- a/src/supermemory/_version.py
+++ b/src/supermemory/_version.py
@@ -1,4 +1,4 @@
 # File generated from our OpenAPI spec by Stainless. See CONTRIBUTING.md for details.
 
 __title__ = "supermemory"
-__version__ = "3.37.0"  # x-release-please-version
+__version__ = "3.38.0"  # x-release-please-version
diff --git a/src/supermemory/resources/documents.py b/src/supermemory/resources/documents.py
index c193aaf..74ba6a4 100644
--- a/src/supermemory/resources/documents.py
+++ b/src/supermemory/resources/documents.py
@@ -496,6 +496,8 @@ def upload_file(
         file: FileTypes,
         container_tag: str | Omit = omit,
         container_tags: str | Omit = omit,
+        custom_id: str | Omit = omit,
+        entity_context: str | Omit = omit,
         filepath: str | Omit = omit,
         file_type: str | Omit = omit,
         metadata: str | Omit = omit,
@@ -521,6 +523,12 @@ def upload_file(
               '["user_123", "project_123"]') or a single string (e.g., 'user_123'). Single
               strings will be automatically converted to an array.
 
+          custom_id: Optional custom ID of the document. Max 100 characters, alphanumeric with
+              hyphens, underscores, and colons only.
+
+          entity_context: Optional entity context for this container tag. Max 1500 characters. Used during
+              document processing to guide memory extraction.
+
           filepath: Optional file path for the uploaded file (e.g., '/documents/reports/file.pdf').
               Used by supermemoryfs to map documents to filesystem paths.
 
@@ -556,6 +564,8 @@ def upload_file(
                 "file": file,
                 "container_tag": container_tag,
                 "container_tags": container_tags,
+                "custom_id": custom_id,
+                "entity_context": entity_context,
                 "filepath": filepath,
                 "file_type": file_type,
                 "metadata": metadata,
@@ -1038,6 +1048,8 @@ async def upload_file(
         file: FileTypes,
         container_tag: str | Omit = omit,
         container_tags: str | Omit = omit,
+        custom_id: str | Omit = omit,
+        entity_context: str | Omit = omit,
         filepath: str | Omit = omit,
         file_type: str | Omit = omit,
         metadata: str | Omit = omit,
@@ -1063,6 +1075,12 @@ async def upload_file(
               '["user_123", "project_123"]') or a single string (e.g., 'user_123'). Single
               strings will be automatically converted to an array.
 
+          custom_id: Optional custom ID of the document. Max 100 characters, alphanumeric with
+              hyphens, underscores, and colons only.
+
+          entity_context: Optional entity context for this container tag. Max 1500 characters. Used during
+              document processing to guide memory extraction.
+
           filepath: Optional file path for the uploaded file (e.g., '/documents/reports/file.pdf').
               Used by supermemoryfs to map documents to filesystem paths.
 
@@ -1098,6 +1116,8 @@ async def upload_file(
                 "file": file,
                 "container_tag": container_tag,
                 "container_tags": container_tags,
+                "custom_id": custom_id,
+                "entity_context": entity_context,
                 "filepath": filepath,
                 "file_type": file_type,
                 "metadata": metadata,
diff --git a/src/supermemory/types/document_upload_file_params.py b/src/supermemory/types/document_upload_file_params.py
index 507fc87..c23911f 100644
--- a/src/supermemory/types/document_upload_file_params.py
+++ b/src/supermemory/types/document_upload_file_params.py
@@ -25,6 +25,18 @@ class DocumentUploadFileParams(TypedDict, total=False):
     converted to an array.
     """
 
+    custom_id: Annotated[str, PropertyInfo(alias="customId")]
+    """Optional custom ID of the document.
+
+    Max 100 characters, alphanumeric with hyphens, underscores, and colons only.
+    """
+
+    entity_context: Annotated[str, PropertyInfo(alias="entityContext")]
+    """Optional entity context for this container tag.
+
+    Max 1500 characters. Used during document processing to guide memory extraction.
+    """
+
     filepath: str
     """Optional file path for the uploaded file (e.g., '/documents/reports/file.pdf').
 
diff --git a/tests/api_resources/test_documents.py b/tests/api_resources/test_documents.py
index 684058a..6abdf99 100644
--- a/tests/api_resources/test_documents.py
+++ b/tests/api_resources/test_documents.py
@@ -438,6 +438,8 @@ def test_method_upload_file_with_all_params(self, client: Supermemory) -> None:
             file=b"Example data",
             container_tag="user",
             container_tags='["user_123", "project_123"]',
+            custom_id="mem_abc123",
+            entity_context="This user is a software engineer who prefers concise technical documentation.",
             filepath="/documents/reports/file.pdf",
             file_type="image",
             metadata='{"category": "technology", "isPublic": true, "readingTime": 5}',
@@ -891,6 +893,8 @@ async def test_method_upload_file_with_all_params(self, async_client: AsyncSuper
             file=b"Example data",
             container_tag="user",
             container_tags='["user_123", "project_123"]',
+            custom_id="mem_abc123",
+            entity_context="This user is a software engineer who prefers concise technical documentation.",
             filepath="/documents/reports/file.pdf",
             file_type="image",
             metadata='{"category": "technology", "isPublic": true, "readingTime": 5}',