diff --git a/src/bridge/bridge.cpp b/src/bridge/bridge.cpp
index b123f63..003288d 100644
--- a/src/bridge/bridge.cpp
+++ b/src/bridge/bridge.cpp
@@ -225,6 +225,7 @@ void Bridge::send_channel_message(const Iid& iid, const std::string& body, std::
     return ;
 
   if (irc->has_capability("draft/multiline")
+      && lines.size() > 1
       // /me and /mode cannot be multi lined
       && lines[0].substr(0, 5) != "/mode"
       && lines[0].substr(0, 4) != "/me ")
@@ -241,13 +242,6 @@ void Bridge::send_channel_message(const Iid& iid, const std::string& body, std::
       if (id.empty())
         id = utils::gen_uuid();
 
-      IrcChannel* channel = irc->get_channel(iid.get_local());
-      if (!channel->joined)
-        {
-          log_warning("Cannot send message to channel ", iid.get_local(), ", it is not joined");
-          return;
-        }
-
       std::vector<IrcMessage> messages;
       for (const std::string& line: lines)
         {
@@ -467,6 +461,41 @@ void Bridge::send_private_message(const Iid& iid, const std::string& body, const
   std::vector<std::string> lines = utils::split(body, '\n', true);
   if (lines.empty())
     return ;
+
+  if (irc->has_capability("draft/multiline")
+      && lines.size() > 1
+      // /me and /mode cannot be multi lined
+      && lines[0].substr(0, 5) != "/mode"
+      && lines[0].substr(0, 4) != "/me ")
+  {
+    std::basic_string<char> uuid = utils::gen_uuid();
+    std::vector<IrcMessage> messages;
+    for (const std::string &line : lines) {
+      constexpr auto max_username_size = 10;
+      constexpr auto max_hostname_size = 63;
+      const auto line_size = 512 - 1 - ::strlen("batch=") - uuid.length() - 1 -
+                             ::strlen("draft/multiline-concat") - 1 -
+                             irc->get_own_nick().size() - max_username_size -
+                             max_hostname_size - ::strlen(":!@ PRIVMSG ") -
+                             iid.get_local().length() - ::strlen(" :\r\n");
+      const auto privmsgs = cut(line, line_size);
+      bool first = true;
+      for (const auto &privmsg : privmsgs) {
+        if (first) {
+          messages.push_back(IrcMessage({}, std::string(), "PRIVMSG",
+                                        {iid.get_local(), privmsg}));
+          first = false;
+        } else
+          messages.push_back(IrcMessage({{"draft/multiline-concat", {}}},
+                                        std::string(), "PRIVMSG",
+                                        {iid.get_local(), privmsg}));
+      }
+    }
+    irc->send_batch(uuid, "draft/multiline", {iid.get_local()}, messages,
+                    [](const IrcClient *, const IrcMessage &) {});
+    return;
+  }
+
   for (const std::string& line: lines)
     {
       if (line.substr(0, 4) == "/me ")
diff --git a/tests/end_to_end/scenarios/multiline_message.py b/tests/end_to_end/scenarios/multiline_message.py
index e26bc90..1e8ab1a 100644
--- a/tests/end_to_end/scenarios/multiline_message.py
+++ b/tests/end_to_end/scenarios/multiline_message.py
@@ -52,5 +52,15 @@ scenario = (
         ["/message[@from='#foo%{irc_server_one}/{nick_one}'][@id='the-message-id'][@to='{jid_one}/{resource_one}'][@type='groupchat']/body[text()='a\nb\nc']"],
 
         ["/message[@from='#foo%{irc_server_one}/{nick_one}'][@id][@to='{jid_two}/{resource_one}'][@type='groupchat']/body[text()='a\nb\nc']"],
-    )
+    ),
+
+    # Send a multi-line private message, to a in-room JID
+    send_stanza("<message from='{jid_one}/{resource_one}' to='#foo%{irc_server_one}/{nick_two}' type='chat'><body>a\nb\nc</body></message>"),
+    # Message is received with a server-wide JID
+    expect_stanza("/message[@from='{lower_nick_one}%{irc_server_one}'][@to='{jid_two}'][@type='chat']/body[text()='a\nb\nc']"),
+
+    # Send a multi-line private message, to a server-wide JID
+    send_stanza("<message from='{jid_one}/{resource_one}' to='{lower_nick_two}%{irc_server_one}' type='chat'><body>a\nb\nc</body></message>"),
+    # Message is received with a server-wide JID
+    expect_stanza("/message[@from='{lower_nick_one}%{irc_server_one}'][@to='{jid_two}'][@type='chat']/body[text()='a\nb\nc']"),
 )