diff --git a/redbot/cogs/audio/core/commands/audioset.py b/redbot/cogs/audio/core/commands/audioset.py
index 2ad0e0bbf61..57194fd649e 100644
--- a/redbot/cogs/audio/core/commands/audioset.py
+++ b/redbot/cogs/audio/core/commands/audioset.py
@@ -758,9 +758,17 @@ async def command_audioset_jukebox(self, ctx: commands.Context, price: int):
         """Set a price for queueing tracks for non-mods, 0 to disable."""
         if price < 0:
             return await self.send_embed_msg(
-                ctx, title=_("Invalid Price"), description=_("Price can't be less than zero.")
+                ctx,
+                title=_("Invalid Price"),
+                description=_("Price can't be less than zero."),
+            )
+        elif price > 2**63 - 1:
+            return await self.send_embed_msg(
+                ctx,
+                title=_("Invalid Price"),
+                description=_("Price can't be greater than 2^63 - 1."),
             )
-        if price == 0:
+        elif price == 0:
             jukebox = False
             await self.send_embed_msg(
                 ctx, title=_("Setting Changed"), description=_("Jukebox mode disabled.")
diff --git a/redbot/cogs/cleanup/cleanup.py b/redbot/cogs/cleanup/cleanup.py
index bd3095f2487..27bd4398fcd 100644
--- a/redbot/cogs/cleanup/cleanup.py
+++ b/redbot/cogs/cleanup/cleanup.py
@@ -54,6 +54,9 @@ async def check_100_plus(ctx: commands.Context, number: int) -> bool:
         if ctx.assume_yes:
             return True
 
+        if number > 2**63 - 1:
+            return await ctx.send(_("Try a smaller number instead."))
+
         prompt = await ctx.send(
             _("Are you sure you want to delete {number} messages?").format(
                 number=humanize_number(number)
diff --git a/redbot/cogs/general/general.py b/redbot/cogs/general/general.py
index 1ffb1b97162..8e251fee594 100644
--- a/redbot/cogs/general/general.py
+++ b/redbot/cogs/general/general.py
@@ -40,7 +40,7 @@ def __init__(self, argument):
             self.choice = None
 
 
-MAX_ROLL: Final[int] = 2**64 - 1
+MAX_ROLL: Final[int] = 2**63 - 1
 
 
 @cog_i18n(_)
diff --git a/redbot/cogs/trivia/converters.py b/redbot/cogs/trivia/converters.py
index 211ed5d4bbe..a5b7a41eedc 100644
--- a/redbot/cogs/trivia/converters.py
+++ b/redbot/cogs/trivia/converters.py
@@ -8,6 +8,9 @@
 _ = Translator("Trivia", __file__)
 
 
+MAX_VALUE = 2**63 - 1
+
+
 def finite_float(arg: str) -> float:
     try:
         ret = float(arg)
diff --git a/redbot/cogs/trivia/session.py b/redbot/cogs/trivia/session.py
index 824d75e5f00..abe31e0aa00 100644
--- a/redbot/cogs/trivia/session.py
+++ b/redbot/cogs/trivia/session.py
@@ -8,6 +8,7 @@
 from redbot.core.i18n import Translator
 from redbot.core.utils.chat_formatting import box, bold, humanize_list, humanize_number
 from redbot.core.utils.common_filters import normalize_smartquotes
+from .converters import MAX_VALUE
 from .log import LOG
 
 __all__ = ["TriviaSession"]
@@ -320,6 +321,7 @@ async def pay_winners(self, multiplier: float):
         if not winners or num_humans < 3:
             return
         payout = int(top_score * multiplier / len(winners))
+        payout = MAX_VALUE if payout > MAX_VALUE else payout
         if payout <= 0:
             return
         for winner in winners:
diff --git a/redbot/core/utils/chat_formatting.py b/redbot/core/utils/chat_formatting.py
index 8cf37e8a267..afcfc2d126d 100644
--- a/redbot/core/utils/chat_formatting.py
+++ b/redbot/core/utils/chat_formatting.py
@@ -576,7 +576,7 @@ def humanize_timedelta(
 
 def humanize_number(val: Union[int, float], override_locale=None) -> str:
     """
-    Convert an int or float to a str with digit separators based on bot locale
+    Convert an int or float to a str with digit separators based on bot locale.
 
     Parameters
     ----------
@@ -585,10 +585,15 @@ def humanize_number(val: Union[int, float], override_locale=None) -> str:
     override_locale: Optional[str]
         A value to override bot's regional format.
 
+    Raises
+    ------
+    decimals.InvalidOperation
+        If val is greater than 10 x 10^21 for some locales, 10 x 10^24 in others.
+
     Returns
     -------
     str
-        locale aware formatted number.
+        Locale-aware formatted number.
     """
     return format_decimal(val, locale=get_babel_regional_format(override_locale))