diff --git a/redbot/core/core_commands.py b/redbot/core/core_commands.py
index 76f17d5b9..69b5fc601 100644
--- a/redbot/core/core_commands.py
+++ b/redbot/core/core_commands.py
@@ -1142,6 +1142,9 @@ class Core(commands.Cog, CoreLogic):
             await ctx.send(
                 _("A backup has been made of this instance. It is at {}.").format(backup_file)
             )
+            if backup_file.stat().st_size > 8_000_000:
+                await ctx.send(_("This backup is to large to send via DM."))
+                return
             await ctx.send(_("Would you like to receive a copy via DM? (y/n)"))
 
             pred = MessagePredicate.yes_or_no(ctx)
@@ -1152,10 +1155,18 @@ class Core(commands.Cog, CoreLogic):
             else:
                 if pred.result is True:
                     await ctx.send(_("OK, it's on its way!"))
-                    async with ctx.author.typing():
-                        await ctx.author.send(
-                            _("Here's a copy of the backup"), file=discord.File(str(backup_file))
+                    try:
+                        async with ctx.author.typing():
+                            await ctx.author.send(
+                                _("Here's a copy of the backup"),
+                                file=discord.File(str(backup_file)),
+                            )
+                    except discord.Forbidden:
+                        await ctx.send(
+                            _("I don't seem to be able to DM you. Do you have closed DMs?")
                         )
+                    except discord.HTTPException:
+                        await ctx.send(_("I could not send the backup file."))
                 else:
                     await ctx.send(_("OK then."))
         else: