diff --git a/astrbot/core/conversation_mgr.py b/astrbot/core/conversation_mgr.py
index c506fa8f1..b0f5c136d 100644
--- a/astrbot/core/conversation_mgr.py
+++ b/astrbot/core/conversation_mgr.py
@@ -175,7 +175,15 @@ class ConversationManager:
             if record["role"] == "user":
                 temp_contexts.append(f"User: {record['content']}")
             elif record["role"] == "assistant":
-                temp_contexts.append(f"Assistant: {record['content']}")
+                if "content" in record and record["content"]:
+                    temp_contexts.append(f"Assistant: {record['content']}")
+                elif "tool_calls" in record:
+                    tool_calls_str = json.dumps(
+                        record["tool_calls"], ensure_ascii=False
+                    )
+                    temp_contexts.append(f"Assistant: [函数调用] {tool_calls_str}")
+                else:
+                    temp_contexts.append("Assistant: [未知的内容]")
                 contexts.insert(0, temp_contexts)
                 temp_contexts = []
 
diff --git a/astrbot/core/pipeline/process_stage/method/llm_request.py b/astrbot/core/pipeline/process_stage/method/llm_request.py
index a7ddd9607..617e458c8 100644
--- a/astrbot/core/pipeline/process_stage/method/llm_request.py
+++ b/astrbot/core/pipeline/process_stage/method/llm_request.py
@@ -66,12 +66,16 @@ class LLMRequestSubStage(Stage):
 
         if event.get_extra("provider_request"):
             req = event.get_extra("provider_request")
-            assert isinstance(req, ProviderRequest), (
-                "provider_request 必须是 ProviderRequest 类型。"
-            )
+            assert isinstance(
+                req, ProviderRequest
+            ), "provider_request 必须是 ProviderRequest 类型。"
 
             if req.conversation:
-                req.contexts = json.loads(req.conversation.history)
+                all_contexts = json.loads(req.conversation.history)
+                req.contexts = self._process_tool_message_pairs(
+                    all_contexts, remove_tags=True
+                )
+
         else:
             req = ProviderRequest(prompt="", image_urls=[])
             if self.provider_wake_prefix:
@@ -447,12 +451,22 @@ class LLMRequestSubStage(Stage):
 
         if llm_response.role == "assistant":
             # 文本回复
-            contexts = req.contexts
+            contexts = req.contexts.copy()
             contexts.append(await req.assemble_context())
 
-            # tool calls result
+            # 记录并标记函数调用结果
             if req.tool_calls_result:
-                contexts.extend(req.tool_calls_result.to_openai_messages())
+                tool_calls_messages = req.tool_calls_result.to_openai_messages()
+
+                # 添加标记
+                for message in tool_calls_messages:
+                    message["_tool_call_history"] = True
+
+                processed_tool_messages = self._process_tool_message_pairs(
+                    tool_calls_messages, remove_tags=False
+                )
+
+                contexts.extend(processed_tool_messages)
 
             contexts.append(
                 {"role": "assistant", "content": llm_response.completion_text}
@@ -463,3 +477,59 @@ class LLMRequestSubStage(Stage):
             await self.conv_manager.update_conversation(
                 event.unified_msg_origin, req.conversation.cid, history=contexts_to_save
             )
+
+    def _process_tool_message_pairs(self, messages, remove_tags=True):
+        """处理工具调用消息，确保assistant和tool消息成对出现
+
+        Args:
+            messages (list): 消息列表
+            remove_tags (bool): 是否移除_tool_call_history标记
+
+        Returns:
+            list: 处理后的消息列表，保证了assistant和对应tool消息的成对出现
+        """
+        result = []
+        i = 0
+
+        while i < len(messages):
+            current_msg = messages[i]
+
+            # 普通消息直接添加
+            if "_tool_call_history" not in current_msg:
+                result.append(current_msg.copy() if remove_tags else current_msg)
+                i += 1
+                continue
+
+            # 工具调用消息成对处理
+            if current_msg.get("role") == "assistant" and "tool_calls" in current_msg:
+                assistant_msg = current_msg.copy()
+
+                if remove_tags and "_tool_call_history" in assistant_msg:
+                    del assistant_msg["_tool_call_history"]
+
+                related_tools = []
+                j = i + 1
+                while (
+                    j < len(messages)
+                    and messages[j].get("role") == "tool"
+                    and "_tool_call_history" in messages[j]
+                ):
+                    tool_msg = messages[j].copy()
+
+                    if remove_tags:
+                        del tool_msg["_tool_call_history"]
+
+                    related_tools.append(tool_msg)
+                    j += 1
+
+                # 成对的时候添加到结果
+                if related_tools:
+                    result.append(assistant_msg)
+                    result.extend(related_tools)
+
+                i = j  # 跳过已处理
+            else:
+                # 单独的tool消息
+                i += 1
+
+        return result
diff --git a/astrbot/core/provider/sources/gemini_source.py b/astrbot/core/provider/sources/gemini_source.py
index 7def203db..a3ca8c8f2 100644
--- a/astrbot/core/provider/sources/gemini_source.py
+++ b/astrbot/core/provider/sources/gemini_source.py
@@ -180,7 +180,7 @@ class ProviderGoogleGenAI(Provider):
             if message["role"] == "user":
                 if isinstance(message["content"], str):
                     if not message["content"]:
-                        message["content"] = ""
+                        message["content"] = " "
 
                     google_genai_conversation.append(
                         {"role": "user", "parts": [{"text": message["content"]}]}
@@ -209,7 +209,7 @@ class ProviderGoogleGenAI(Provider):
             elif message["role"] == "assistant":
                 if "content" in message:
                     if not message["content"]:
-                        message["content"] = ""
+                        message["content"] = " "
                     google_genai_conversation.append(
                         {"role": "model", "parts": [{"text": message["content"]}]}
                     )