diff --git a/nonebot/matcher.py b/nonebot/matcher.py
index 095d3320..0d552d9f 100644
--- a/nonebot/matcher.py
+++ b/nonebot/matcher.py
@@ -505,7 +505,7 @@ class Matcher(metaclass=MatcherMeta):
         """
         bot = current_bot.get()
         event = current_event.get()
-        if message:
+        if message is not None:
             await bot.send(event=event, message=message, **kwargs)
         raise FinishedException
 
@@ -571,6 +571,7 @@ class Matcher(metaclass=MatcherMeta):
 
             while self.handlers:
                 handler = self.handlers.pop(0)
+                logger.debug(f"Running handler {handler}")
                 await handler(self, bot, event, self.state)
 
         except RejectedException:
diff --git a/packages/nonebot-adapter-ding/nonebot/adapters/ding/bot.py b/packages/nonebot-adapter-ding/nonebot/adapters/ding/bot.py
index 57dac284..2900a8d3 100644
--- a/packages/nonebot-adapter-ding/nonebot/adapters/ding/bot.py
+++ b/packages/nonebot-adapter-ding/nonebot/adapters/ding/bot.py
@@ -114,7 +114,7 @@ class Bot(BaseBot):
                         api: str,
                         event: Optional[MessageEvent] = None,
                         **data) -> Any:
-        if self.connection_type != "http":
+        if not isinstance(self.request, HTTPRequest):
             log("ERROR", "Only support http connection.")
             return
 
diff --git a/packages/nonebot-adapter-ding/nonebot/adapters/ding/message.py b/packages/nonebot-adapter-ding/nonebot/adapters/ding/message.py
index eb7d655d..42012f9e 100644
--- a/packages/nonebot-adapter-ding/nonebot/adapters/ding/message.py
+++ b/packages/nonebot-adapter-ding/nonebot/adapters/ding/message.py
@@ -17,12 +17,21 @@ class MessageSegment(BaseMessageSegment["Message"]):
 
     @overrides(BaseMessageSegment)
     def __str__(self) -> str:
+        """
+        该消息段所代表的 str，在命令匹配部分使用，
+        钉钉目前只支持匹配 text 命令
+        """
         if self.type == "text":
             return str(self.data["content"])
-        elif self.type == "markdown":
-            return str(self.data["text"])
         return ""
 
+    def __bool__(self) -> bool:
+        """
+        因为暂时还不支持 text 和 markdown 之外的其他复杂消息段的 `__str__`（也不太需要），
+        会导致判断非这两种类型的消息段的布尔值为 true 的时候出错
+        """
+        return self.data is not None
+
     @overrides(BaseMessageSegment)
     def is_text(self) -> bool:
         return self.type == "text"