diff --git a/discord/app_commands/checks.py b/discord/app_commands/checks.py
index 7b7d45041..fcc97260a 100644
--- a/discord/app_commands/checks.py
+++ b/discord/app_commands/checks.py
@@ -112,7 +112,8 @@ class Cooldown:
         if not current:
             current = time.time()
 
-        tokens = self._tokens
+        # the calculated tokens should be non-negative
+        tokens = max(self._tokens, 0)
 
         if current > self._window + self.per:
             tokens = self.rate
@@ -140,7 +141,7 @@ class Cooldown:
 
         return 0.0
 
-    def update_rate_limit(self, current: Optional[float] = None) -> Optional[float]:
+    def update_rate_limit(self, current: Optional[float] = None, *, tokens: int = 1) -> Optional[float]:
         """Updates the cooldown rate limit.
 
         Parameters
@@ -148,6 +149,8 @@ class Cooldown:
         current: Optional[:class:`float`]
             The time in seconds since Unix epoch to update the rate limit at.
             If not supplied, then :func:`time.time()` is used.
+        tokens: :class:`int`
+            The amount of tokens to deduct from the rate limit.
 
         Returns
         -------
@@ -163,12 +166,12 @@ class Cooldown:
         if self._tokens == self.rate:
             self._window = current
 
-        # check if we are rate limited
-        if self._tokens == 0:
-            return self.per - (current - self._window)
+        # decrement tokens by specified number
+        self._tokens -= tokens
 
-        # we're not so decrement our tokens
-        self._tokens -= 1
+        # check if we are rate limited and return retry-after
+        if self._tokens < 0:
+            return self.per - (current - self._window)
 
     def reset(self) -> None:
         """Reset the cooldown to its initial state."""
diff --git a/discord/ext/commands/cooldowns.py b/discord/ext/commands/cooldowns.py
index 534658728..fc57e22e0 100644
--- a/discord/ext/commands/cooldowns.py
+++ b/discord/ext/commands/cooldowns.py
@@ -140,9 +140,9 @@ class CooldownMapping:
 
         return bucket
 
-    def update_rate_limit(self, message: Message, current: Optional[float] = None) -> Optional[float]:
+    def update_rate_limit(self, message: Message, current: Optional[float] = None, tokens: int = 1) -> Optional[float]:
         bucket = self.get_bucket(message, current)
-        return bucket.update_rate_limit(current)
+        return bucket.update_rate_limit(current, tokens=tokens)
 
 
 class DynamicCooldownMapping(CooldownMapping):