diff --git a/src/callbacks.py b/src/callbacks.py
index e198b54a6..4a109f3bf 100644
--- a/src/callbacks.py
+++ b/src/callbacks.py
@@ -906,7 +906,9 @@ class NestedCommandsIrcProxy(ReplyIrcProxy):
                         log.warning('Truncating to %s bytes from %s bytes.',
                                     maximumLength, len(s))
                         s = s[:maximumLength]
-                    if len(s) < allowedLength or \
+                    s_too_long = len(s.encode()) < allowedLength \
+                            if minisix.PY3 else len(s) < allowedLength
+                    if s_too_long or \
                        not conf.get(conf.supybot.reply.mores, target):
                         # In case we're truncating, we add 20 to allowedLength,
                         # because our allowedLength is shortened for the