diff --git a/redbot/core/bot.py b/redbot/core/bot.py
index d274526fdf7..0e3e0cb2d40 100644
--- a/redbot/core/bot.py
+++ b/redbot/core/bot.py
@@ -2502,6 +2502,7 @@ async def send_interactive(
             n_remaining = len(messages) - idx
             files_perm = (
                 isinstance(channel, discord.abc.User)
+                or channel.guild is None
                 or channel.permissions_for(channel.guild.me).attach_files
             )
             options = ("more", "file") if files_perm else ("more",)