diff --git a/CHANGELOG.md b/CHANGELOG.md
index 7e5419fdac..64fa2d8362 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -49,6 +49,7 @@ No changes to highlight.
 ## Testing and Infrastructure Changes:
 
 - CI: Simplified Python CI workflow by [@akx](https://github.com/akx) in [PR 3982](https://github.com/gradio-app/gradio/pull/3982)
+- Upgrade pyright to 1.1.305 by [@akx](https://github.com/akx) in [PR 4042](https://github.com/gradio-app/gradio/pull/4042)
 
 ## Breaking Changes:
 
diff --git a/client/python/test/requirements.txt b/client/python/test/requirements.txt
index f7429a7d86..0a0e97bcb9 100644
--- a/client/python/test/requirements.txt
+++ b/client/python/test/requirements.txt
@@ -2,5 +2,5 @@ black==22.6.0
 pytest-asyncio
 pytest==7.1.2
 ruff==0.0.263
-pyright==1.1.298
+pyright==1.1.305
 gradio
diff --git a/gradio/flagging.py b/gradio/flagging.py
index 5f2a81969a..89b65f888d 100644
--- a/gradio/flagging.py
+++ b/gradio/flagging.py
@@ -418,7 +418,7 @@ class HuggingFaceDatasetSaver(FlaggingCallback):
             row.append(Path(deserialized).name)
 
             # If component is eligible for a preview, add the URL of the file
-            if isinstance(component, tuple(FILE_PREVIEW_TYPES)):
+            if isinstance(component, tuple(FILE_PREVIEW_TYPES)):  # type: ignore
                 for _component, _type in FILE_PREVIEW_TYPES.items():
                     if isinstance(component, _component):
                         features[label + " file"] = {"_type": _type}
diff --git a/test/requirements-37.txt b/test/requirements-37.txt
index 841e0e9982..0967672ed3 100644
--- a/test/requirements-37.txt
+++ b/test/requirements-37.txt
@@ -163,7 +163,7 @@ pygments==2.12.0
     # via ipython
 pyparsing==3.0.9
     # via packaging
-pyright==1.1.298
+pyright==1.1.305
 pyrsistent==0.18.1
     # via jsonschema
 pytest==7.1.2
diff --git a/test/requirements.txt b/test/requirements.txt
index eb8b77b344..2ddc10dcd1 100644
--- a/test/requirements.txt
+++ b/test/requirements.txt
@@ -168,7 +168,7 @@ python-dateutil==2.8.2
     # via
     #   botocore
     #   pandas
-pyright==1.1.298
+pyright==1.1.305
 pytz==2022.1
     # via pandas
 pywavelets==1.3.0