diff --git a/CHANGES/10099.bugfix.rst b/CHANGES/10099.bugfix.rst
new file mode 100644
index 00000000000..718420a6ad5
--- /dev/null
+++ b/CHANGES/10099.bugfix.rst
@@ -0,0 +1 @@
+Fixed type of ``SSLContext`` for some static type checkers (e.g. pyright).
diff --git a/CONTRIBUTORS.txt b/CONTRIBUTORS.txt
index 6adb3b97fb1..ded6c463e40 100644
--- a/CONTRIBUTORS.txt
+++ b/CONTRIBUTORS.txt
@@ -9,6 +9,7 @@ Adam Mills
 Adrian Krupa
 Adrián Chaves
 Ahmed Tahri
+Alan Bogarin
 Alan Tse
 Alec Hanefeld
 Alejandro Gómez
diff --git a/aiohttp/client_exceptions.py b/aiohttp/client_exceptions.py
index 667da8d5084..1d298e9a8cf 100644
--- a/aiohttp/client_exceptions.py
+++ b/aiohttp/client_exceptions.py
@@ -8,13 +8,17 @@
 
 from .typedefs import StrOrURL
 
-try:
+if TYPE_CHECKING:
     import ssl
 
     SSLContext = ssl.SSLContext
-except ImportError:  # pragma: no cover
-    ssl = SSLContext = None  # type: ignore[assignment]
+else:
+    try:
+        import ssl
 
+        SSLContext = ssl.SSLContext
+    except ImportError:  # pragma: no cover
+        ssl = SSLContext = None  # type: ignore[assignment]
 
 if TYPE_CHECKING:
     from .client_reqrep import ClientResponse, ConnectionKey, Fingerprint, RequestInfo
diff --git a/aiohttp/client_reqrep.py b/aiohttp/client_reqrep.py
index e97c40ce0e5..43b48063c6e 100644
--- a/aiohttp/client_reqrep.py
+++ b/aiohttp/client_reqrep.py
@@ -72,12 +72,16 @@
     RawHeaders,
 )
 
-try:
+if TYPE_CHECKING:
     import ssl
     from ssl import SSLContext
-except ImportError:  # pragma: no cover
-    ssl = None  # type: ignore[assignment]
-    SSLContext = object  # type: ignore[misc,assignment]
+else:
+    try:
+        import ssl
+        from ssl import SSLContext
+    except ImportError:  # pragma: no cover
+        ssl = None  # type: ignore[assignment]
+        SSLContext = object  # type: ignore[misc,assignment]
 
 
 __all__ = ("ClientRequest", "ClientResponse", "RequestInfo", "Fingerprint")
diff --git a/aiohttp/connector.py b/aiohttp/connector.py
index 93bc2513b20..a9123f82bc0 100644
--- a/aiohttp/connector.py
+++ b/aiohttp/connector.py
@@ -60,14 +60,18 @@
 )
 from .resolver import DefaultResolver
 
-try:
+if TYPE_CHECKING:
     import ssl
 
     SSLContext = ssl.SSLContext
-except ImportError:  # pragma: no cover
-    ssl = None  # type: ignore[assignment]
-    SSLContext = object  # type: ignore[misc,assignment]
-
+else:
+    try:
+        import ssl
+
+        SSLContext = ssl.SSLContext
+    except ImportError:  # pragma: no cover
+        ssl = None  # type: ignore[assignment]
+        SSLContext = object  # type: ignore[misc,assignment]
 
 EMPTY_SCHEMA_SET = frozenset({""})
 HTTP_SCHEMA_SET = frozenset({"http", "https"})
diff --git a/aiohttp/web.py b/aiohttp/web.py
index f975b665331..d6ab6f6fad4 100644
--- a/aiohttp/web.py
+++ b/aiohttp/web.py
@@ -9,6 +9,7 @@
 from contextlib import suppress
 from importlib import import_module
 from typing import (
+    TYPE_CHECKING,
     Any,
     Awaitable,
     Callable,
@@ -287,10 +288,13 @@
 )
 
 
-try:
+if TYPE_CHECKING:
     from ssl import SSLContext
-except ImportError:  # pragma: no cover
-    SSLContext = Any  # type: ignore[misc,assignment]
+else:
+    try:
+        from ssl import SSLContext
+    except ImportError:  # pragma: no cover
+        SSLContext = object  # type: ignore[misc,assignment]
 
 # Only display warning when using -Wdefault, -We, -X dev or similar.
 warnings.filterwarnings("ignore", category=NotAppKeyWarning, append=True)
diff --git a/aiohttp/web_runner.py b/aiohttp/web_runner.py
index f8933383435..bcfec727c84 100644
--- a/aiohttp/web_runner.py
+++ b/aiohttp/web_runner.py
@@ -3,7 +3,7 @@
 import socket
 import warnings
 from abc import ABC, abstractmethod
-from typing import Any, List, Optional, Set
+from typing import TYPE_CHECKING, Any, List, Optional, Set
 
 from yarl import URL
 
@@ -11,11 +11,13 @@
 from .web_app import Application
 from .web_server import Server
 
-try:
+if TYPE_CHECKING:
     from ssl import SSLContext
-except ImportError:
-    SSLContext = object  # type: ignore[misc,assignment]
-
+else:
+    try:
+        from ssl import SSLContext
+    except ImportError:  # pragma: no cover
+        SSLContext = object  # type: ignore[misc,assignment]
 
 __all__ = (
     "BaseSite",
diff --git a/aiohttp/worker.py b/aiohttp/worker.py
index 9b307697336..8ed121ac955 100644
--- a/aiohttp/worker.py
+++ b/aiohttp/worker.py
@@ -6,7 +6,7 @@
 import signal
 import sys
 from types import FrameType
-from typing import Any, Awaitable, Callable, Optional, Union  # noqa
+from typing import TYPE_CHECKING, Any, Optional
 
 from gunicorn.config import AccessLogFormat as GunicornAccessLogFormat
 from gunicorn.workers import base
@@ -17,13 +17,18 @@
 from .web_app import Application
 from .web_log import AccessLogger
 
-try:
+if TYPE_CHECKING:
     import ssl
 
     SSLContext = ssl.SSLContext
-except ImportError:  # pragma: no cover
-    ssl = None  # type: ignore[assignment]
-    SSLContext = object  # type: ignore[misc,assignment]
+else:
+    try:
+        import ssl
+
+        SSLContext = ssl.SSLContext
+    except ImportError:  # pragma: no cover
+        ssl = None  # type: ignore[assignment]
+        SSLContext = object  # type: ignore[misc,assignment]
 
 
 __all__ = ("GunicornWebWorker", "GunicornUVLoopWebWorker")
diff --git a/docs/spelling_wordlist.txt b/docs/spelling_wordlist.txt
index a1f3d944584..c4e10b44987 100644
--- a/docs/spelling_wordlist.txt
+++ b/docs/spelling_wordlist.txt
@@ -245,6 +245,7 @@ py
 pydantic
 pyenv
 pyflakes
+pyright
 pytest
 Pytest
 Quickstart