diff --git a/corporate/lib/stripe.py b/corporate/lib/stripe.py
index b1ddce9314..97be717043 100644
--- a/corporate/lib/stripe.py
+++ b/corporate/lib/stripe.py
@@ -500,7 +500,7 @@ def catch_stripe_errors(func: Callable[ParamT, ReturnT]) -> Callable[ParamT, Ret
                 err.get("code"),
                 err.get("param"),
             )
-            if isinstance(e, (stripe.RateLimitError, stripe.APIConnectionError)):  # nocoverage TODO
+            if isinstance(e, stripe.RateLimitError | stripe.APIConnectionError):  # nocoverage TODO
                 raise StripeConnectionError(
                     "stripe connection error",
                     _("Something went wrong. Please wait a few seconds and try again."),
@@ -3252,7 +3252,7 @@ class BillingSession(ABC):
     def get_sponsorship_request_context(self) -> dict[str, Any] | None:
         customer = self.get_customer()
         is_remotely_hosted = isinstance(
-            self, (RemoteRealmBillingSession, RemoteServerBillingSession)
+            self, RemoteRealmBillingSession | RemoteServerBillingSession
         )
 
         plan_name = "Zulip Cloud Free"
diff --git a/corporate/tests/test_stripe.py b/corporate/tests/test_stripe.py
index 32d443f43c..3e69ebabce 100644
--- a/corporate/tests/test_stripe.py
+++ b/corporate/tests/test_stripe.py
@@ -6495,7 +6495,7 @@ class TestRemoteBillingWriteAuditLog(StripeTestCase):
             audit_log_model = cast(
                 type[RemoteRealmAuditLog] | type[RemoteZulipServerAuditLog], audit_log_class
             )
-            assert isinstance(remote_user, (RemoteRealmBillingUser, RemoteServerBillingUser))
+            assert isinstance(remote_user, RemoteRealmBillingUser | RemoteServerBillingUser)
             # No acting user:
             session = session_class(remote_object)
             session.write_to_audit_log(
diff --git a/zerver/lib/data_types.py b/zerver/lib/data_types.py
index ffdabe316b..5f23670f5f 100644
--- a/zerver/lib/data_types.py
+++ b/zerver/lib/data_types.py
@@ -113,7 +113,7 @@ class NumberType:
     OpenAPI, because isinstance(4, float) == False"""
 
     def check_data(self, var_name: str, val: Any | None) -> None:
-        if isinstance(val, (int, float)):
+        if isinstance(val, int | float):
             return
         raise AssertionError(f"{var_name} is not a number")
 
@@ -185,7 +185,7 @@ class TupleType:
     sub_types: Sequence[Any]
 
     def check_data(self, var_name: str, val: Any) -> None:
-        if not isinstance(val, (list, tuple)):
+        if not isinstance(val, list | tuple):
             raise AssertionError(f"{var_name} is not a list/tuple")
 
         if len(val) != len(self.sub_types):
diff --git a/zerver/lib/validator.py b/zerver/lib/validator.py
index 948218bce9..80345500b7 100644
--- a/zerver/lib/validator.py
+++ b/zerver/lib/validator.py
@@ -624,7 +624,7 @@ def check_string_or_int_list(var_name: str, val: object) -> str | list[int]:
 
 
 def check_string_or_int(var_name: str, val: object) -> str | int:
-    if isinstance(val, (str, int)):
+    if isinstance(val, str | int):
         return val
 
     raise ValidationError(_("{var_name} is not a string or integer").format(var_name=var_name))
@@ -654,7 +654,7 @@ class WildValue:
         return self.value == other
 
     def __len__(self) -> int:
-        if not isinstance(self.value, (dict, list, str)):
+        if not isinstance(self.value, dict | list | str):
             raise ValidationError(
                 _("{var_name} does not have a length").format(var_name=self.var_name)
             )
diff --git a/zerver/openapi/markdown_extension.py b/zerver/openapi/markdown_extension.py
index fcf8f14065..cb219d9521 100644
--- a/zerver/openapi/markdown_extension.py
+++ b/zerver/openapi/markdown_extension.py
@@ -254,7 +254,7 @@ cURL example."""
 
         # Booleans are effectively JSON-encoded, in that we pass
         # true/false, not the Python str(True) = "True"
-        if parameter.json_encoded or isinstance(example_value, (bool, float, int)):
+        if parameter.json_encoded or isinstance(example_value, bool | float | int):
             example_value = json.dumps(example_value)
         else:
             assert isinstance(example_value, str)
diff --git a/zerver/views/registration.py b/zerver/views/registration.py
index 70fc282650..f478242566 100644
--- a/zerver/views/registration.py
+++ b/zerver/views/registration.py
@@ -175,7 +175,7 @@ def check_prereg_key(
     prereg_object = get_object_from_key(
         confirmation_key, confirmation_types, mark_object_used=False
     )
-    assert isinstance(prereg_object, (PreregistrationRealm, PreregistrationUser))
+    assert isinstance(prereg_object, PreregistrationRealm | PreregistrationUser)
 
     confirmation_obj = prereg_object.confirmation.get()
     realm_creation = confirmation_obj.type == Confirmation.REALM_CREATION
diff --git a/zerver/views/sentry.py b/zerver/views/sentry.py
index f21fb4f219..ead60b929e 100644
--- a/zerver/views/sentry.py
+++ b/zerver/views/sentry.py
@@ -100,7 +100,7 @@ def sentry_tunnel(
 # failing to connect at the TCP level will report as
 # ProxyErrors.
 def open_circuit_for(exc_type: type[Exception], exc_value: Exception) -> bool:
-    if issubclass(exc_type, (ProxyError, Timeout)):
+    if issubclass(exc_type, ProxyError | Timeout):
         return True
     if isinstance(exc_value, HTTPError):
         response = exc_value.response