diff --git a/CHANGELOG.md b/CHANGELOG.md
index 11064e709b..4444d79d1a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -190,6 +190,8 @@ These changes are available on the `master` branch, but have not yet been releas
   ([#2113](https://github.com/Pycord-Development/pycord/issues/2113))
 - Fixed `Option` not working on bridge commands because `ext.commands.Command` doesn't
   recognize them. ([#2256](https://github.com/Pycord-Development/pycord/pull/2256))
+- Fixed offset-aware tasks causing `TypeError` when being prepared.
+  ([#2271](https://github.com/Pycord-Development/pycord/pull/2271))
 - Fixed `AttributeError` when serializing commands with `Annotated` type hints.
   ([#2243](https://github.com/Pycord-Development/pycord/pull/2243))
 
diff --git a/discord/ext/tasks/__init__.py b/discord/ext/tasks/__init__.py
index 81d39ab8d1..638bd831c6 100644
--- a/discord/ext/tasks/__init__.py
+++ b/discord/ext/tasks/__init__.py
@@ -619,9 +619,9 @@ def _prepare_time_index(self, now: datetime.datetime = MISSING) -> None:
             now
             if now is not MISSING
             else datetime.datetime.now(datetime.timezone.utc).replace(microsecond=0)
-        ).timetz()
+        )
         for idx, time in enumerate(self._time):
-            if time >= time_now:
+            if time >= time_now.astimezone(time.tzinfo).timetz():
                 self._time_index = idx
                 break
         else:
diff --git a/requirements/dev.txt b/requirements/dev.txt
index 525873d774..f77e9309c2 100644
--- a/requirements/dev.txt
+++ b/requirements/dev.txt
@@ -1,5 +1,5 @@
 -r _.txt
-pylint~=2.17.5
+pylint~=3.0.2
 pytest~=7.4.3
 pytest-asyncio~=0.21.1
 # pytest-order~=1.0.1