diff --git a/dev-requirements.txt b/dev-requirements.txt
index 39c25f980..0224d4df2 100644
--- a/dev-requirements.txt
+++ b/dev-requirements.txt
@@ -22,7 +22,9 @@ sphinx-rfcsection~=0.1.1
 vcrpy @ git+https://github.com/sopel-irc/vcrpy@uncap-urllib3
 # type check
 mypy>=1.3,<2
+# for `pkg_resources`; first version in which it's typed
+# we don't use `pkg_resources` directly, but mypy still cares
+setuptools>=71.1
 sqlalchemy[mypy]>=1.4,<1.5
-types-pkg-resources~=0.1.3
 types-pytz
 types-requests>=2,<3
diff --git a/pyproject.toml b/pyproject.toml
index bc7dc8e49..2e1ccbce6 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -52,6 +52,7 @@ dependencies = [
     "importlib_metadata>=3.6",
     "packaging>=23.2",
     "sopel-help>=0.4.0",
+    "typing_extensions>=4.4",  # for @typing.override, added in py3.12
 ]
 
 [project.urls]
diff --git a/sopel/tools/__init__.py b/sopel/tools/__init__.py
index f391f0005..8fcd13c6a 100644
--- a/sopel/tools/__init__.py
+++ b/sopel/tools/__init__.py
@@ -160,7 +160,7 @@ def write(self, string):
 
         :param str string: the string to write
         """
-        if not self.quiet:
+        if not self.quiet and sys.__stderr__ and sys.__stdout__:
             try:
                 if self.stderr:
                     sys.__stderr__.write(string)
@@ -179,9 +179,9 @@ def write(self, string):
 
     def flush(self):
         """Flush the file writing buffer."""
-        if self.stderr:
+        if self.stderr and sys.__stderr__:
             sys.__stderr__.flush()
-        else:
+        elif sys.__stdout__:
             sys.__stdout__.flush()
 
 
diff --git a/sopel/tools/memories.py b/sopel/tools/memories.py
index f38c51864..1fb2b0b2a 100644
--- a/sopel/tools/memories.py
+++ b/sopel/tools/memories.py
@@ -10,6 +10,8 @@
 import threading
 from typing import Any, Optional, TYPE_CHECKING, Union
 
+from typing_extensions import override
+
 from .identifiers import Identifier, IdentifierFactory
 
 if TYPE_CHECKING:
@@ -259,6 +261,7 @@ def pop(self, key: str, default=_NO_DEFAULT):
             return super().pop(self._make_key(key))
         return super().pop(self._make_key(key), default)
 
+    @override
     def update(self, maybe_mapping=tuple()):
         """Update this ``SopelIdentifierMemory`` with key-value pairs.