diff --git a/src/bobbit/protocol/irc.py b/src/bobbit/protocol/irc.py
index dfb5375..9069dd2 100644
--- a/src/bobbit/protocol/irc.py
+++ b/src/bobbit/protocol/irc.py
@@ -25,7 +25,11 @@
 NICK_RE       = re.compile(r':(?P<old_nick>.*?)!\S+\s+?NICK\s+(?P<new_nick>[^\s]+)')
 REGISTERED_RE = re.compile(r':NickServ!.*NOTICE.*:.*(identified|logged in|accepted).*')
 
-MESSAGE_LENGTH_MAX = 512 - len(CRNL)
+# NOTE: IRC message length limit is 512 bytes, but that includes the sender's hostmask
+# since the hostmask can change during a session, the simplest way to ensure messages are under 512 bytes
+# is to set a conservative maximum like 400
+# so few bobbit messages are that long that it shouldn't cost too many extra messages being sent
+MESSAGE_LENGTH_MAX = 400
 
 # IRC Client
 
@@ -149,9 +153,10 @@ async def send_message(self, message):
         if isinstance(message, Message):
             message = self.format_message(message)
 
-        if len(message) > MESSAGE_LENGTH_MAX:
+        # NOTE: use str.encode() to determine length of message/command since IRC only cares about number of bytes
+        if len(message.encode()) > MESSAGE_LENGTH_MAX:
             command, message = message.split(' :', 1)
-            messages = [f'{command} :{m}' for m in textwrap.wrap(message, MESSAGE_LENGTH_MAX - len(command) - 2)]
+            messages = [f'{command} :{m}' for m in textwrap.wrap(message, MESSAGE_LENGTH_MAX - len(command.encode()) - 2)]
         else:
             messages = [message]