diff --git a/stdlib/signal.pyi b/stdlib/signal.pyi
index e0d7364c6..d1bd69306 100644
--- a/stdlib/signal.pyi
+++ b/stdlib/signal.pyi
@@ -113,7 +113,7 @@ else:
     SIGXCPU: Signals
     SIGXFSZ: Signals
 
-    class ItimerError(IOError): ...
+    class ItimerError(OSError): ...
     ITIMER_PROF: int
     ITIMER_REAL: int
     ITIMER_VIRTUAL: int
diff --git a/stdlib/urllib/error.pyi b/stdlib/urllib/error.pyi
index 488e0a9bc..89cec9bf2 100644
--- a/stdlib/urllib/error.pyi
+++ b/stdlib/urllib/error.pyi
@@ -4,7 +4,7 @@ from urllib.response import addinfourl
 
 __all__ = ["URLError", "HTTPError", "ContentTooShortError"]
 
-class URLError(IOError):
+class URLError(OSError):
     reason: str | BaseException
     def __init__(self, reason: str | BaseException, filename: str | None = None) -> None: ...
 
diff --git a/stubs/Pillow/PIL/__init__.pyi b/stubs/Pillow/PIL/__init__.pyi
index 8873f33c3..73d7019df 100644
--- a/stubs/Pillow/PIL/__init__.pyi
+++ b/stubs/Pillow/PIL/__init__.pyi
@@ -1,3 +1,3 @@
 __version__: str
 
-class UnidentifiedImageError(IOError): ...
+class UnidentifiedImageError(OSError): ...
diff --git a/stubs/docutils/docutils/io.pyi b/stubs/docutils/docutils/io.pyi
index 12605312d..cc836380a 100644
--- a/stubs/docutils/docutils/io.pyi
+++ b/stubs/docutils/docutils/io.pyi
@@ -14,8 +14,8 @@ from docutils import TransformSpec
 
 __docformat__: str
 
-class InputError(IOError): ...
-class OutputError(IOError): ...
+class InputError(OSError): ...
+class OutputError(OSError): ...
 
 def check_encoding(stream: Any, encoding: str) -> bool | None: ...
 def error_string(err: BaseException) -> str: ...
diff --git a/stubs/paramiko/paramiko/buffered_pipe.pyi b/stubs/paramiko/paramiko/buffered_pipe.pyi
index 7a6760279..c31584e50 100644
--- a/stubs/paramiko/paramiko/buffered_pipe.pyi
+++ b/stubs/paramiko/paramiko/buffered_pipe.pyi
@@ -1,7 +1,7 @@
 from threading import Event
 from typing import AnyStr, Generic
 
-class PipeTimeout(IOError): ...
+class PipeTimeout(OSError): ...
 
 class BufferedPipe(Generic[AnyStr]):
     def __init__(self) -> None: ...
diff --git a/stubs/requests/requests/exceptions.pyi b/stubs/requests/requests/exceptions.pyi
index 88479bbca..b642d5ad3 100644
--- a/stubs/requests/requests/exceptions.pyi
+++ b/stubs/requests/requests/exceptions.pyi
@@ -2,7 +2,7 @@ from typing import Any
 
 from urllib3.exceptions import HTTPError as BaseHTTPError
 
-class RequestException(IOError):
+class RequestException(OSError):
     response: Any
     request: Any
     def __init__(self, *args, **kwargs) -> None: ...