diff --git a/src/obelisk/asynchronous/base.py b/src/obelisk/asynchronous/base.py
index bb1856f..a291b57 100644
--- a/src/obelisk/asynchronous/base.py
+++ b/src/obelisk/asynchronous/base.py
@@ -99,7 +99,7 @@ async def _verify_token(self) -> None:
         if (
             self._token is None
             or self._token_expires is None
-            or self._token_expires < (datetime.now() - self.grace_period)
+            or self._token_expires >= (datetime.now() - self.grace_period)
         ):
             retry = self.retry_strategy.make()
             first = True