From 06bd7852c8919a26fc789f0f70f4730b012d8b4d Mon Sep 17 00:00:00 2001
From: 1cbyc <isaacnsisong@gmail.com>
Date: Fri, 25 Sep 2026 20:32:25 +0000
Subject: [PATCH] fix: send long Discord replies in chunks

Co-authored-by: insisong <emmanuelisaacnsisong@gmail.com>
---
 taskuary/outbound.py         |  6 +++++-
 tests/test_reply_channels.py | 24 ++++++++++++++++++++++++
 2 files changed, 29 insertions(+), 1 deletion(-)

diff --git a/taskuary/outbound.py b/taskuary/outbound.py
index 8d0b7821..a4132b26 100644
--- a/taskuary/outbound.py
+++ b/taskuary/outbound.py
@@ -604,11 +604,15 @@ def reply_to_message(store, msg: dict, body: str, to: list = None, cc: list = No
         connector_id = _source_connector_id(store, 'imessage', chat)
         return send_text(store, chat, body, connector_id) if connector_id else send_text(store, chat, body)
     if ch == 'discord':
+        from . import chatformat
         from .devtools import discord_send
         chat = str(msg.get('ConversationId') or '').split(':', 1)[-1]   # 'discord:<channel_id>'
         if not chat: raise RuntimeError('this chat message has no channel id to answer in')
         connector_id = _source_connector_id(store, 'discord', chat)
-        return discord_send(store, chat, body, connector_id) if connector_id else discord_send(store, chat, body)
+        pieces = chatformat.split(body, 1900)
+        sent = [discord_send(store, chat, piece, connector_id) if connector_id else
+                discord_send(store, chat, piece) for piece in pieces]
+        return sent[0]
     if ch in CHAT_SERVERS:
         from . import chatservers
         chat = str(msg.get('ConversationId') or '').split(':', 1)[-1]   # '<type>:<room id>'
diff --git a/tests/test_reply_channels.py b/tests/test_reply_channels.py
index 6a462113..3b9ce21c 100644
--- a/tests/test_reply_channels.py
+++ b/tests/test_reply_channels.py
@@ -48,6 +48,30 @@ def test_case_and_blank_are_handled(self):
         self.assertFalse(outbound.can_reply(s, None))
 
 
+class DiscordReplyTests(unittest.TestCase):
+    def test_long_reply_is_sent_in_order_without_loss(self):
+        s = MemoryStore()
+        body = 'x' * 5000
+        msg = {'Channel': 'discord', 'ConversationId': 'discord:555', 'ExternalId': 'discord:1'}
+
+        with mock.patch('taskuary.devtools.discord_send', return_value={'channel': 'discord'}) as send:
+            outbound.reply_to_message(s, msg, body)
+
+        pieces = [call.args[2] for call in send.call_args_list]
+        self.assertEqual(len(pieces), 3)
+        self.assertTrue(all(len(piece) <= 2000 for piece in pieces))
+        self.assertEqual(''.join(pieces), body)
+
+    def test_short_reply_is_sent_once_unchanged(self):
+        s = MemoryStore()
+        msg = {'Channel': 'discord', 'ConversationId': 'discord:555', 'ExternalId': 'discord:1'}
+
+        with mock.patch('taskuary.devtools.discord_send', return_value={'channel': 'discord'}) as send:
+            outbound.reply_to_message(s, msg, 'On it.')
+
+        send.assert_called_once_with(s, '555', 'On it.')
+
+
 class FinishTests(unittest.TestCase):
     """coder.finish is the truth, and the UI promises exactly what it did: a channel that cannot carry the
     reply still gets its draft (the always-draft rule, PW-237) - Send is hidden and the reason said."""