diff --git a/extensions/openai/completions.py b/extensions/openai/completions.py
index 10cdbf42..37e9568a 100644
--- a/extensions/openai/completions.py
+++ b/extensions/openai/completions.py
@@ -239,12 +239,14 @@ def convert_history(history):
     user_input = ""
     user_input_last = True
     system_message = ""
+    seen_non_system = False
 
     for entry in history:
         content = entry["content"]
         role = entry["role"]
 
         if role == "user":
+            seen_non_system = True
             # Extract text content (images handled by model-specific code)
             content = process_multimodal_content(content)
             user_input = content
@@ -256,6 +258,7 @@ def convert_history(history):
 
             current_message = content
         elif role == "assistant":
+            seen_non_system = True
             meta = {}
             tool_calls = entry.get("tool_calls")
             if tool_calls and isinstance(tool_calls, list) and len(tool_calls) > 0:
@@ -272,13 +275,22 @@ def convert_history(history):
             else:
                 chat_dialogue.append(['', current_reply, '', meta])
         elif role == "tool":
+            seen_non_system = True
             user_input_last = False
             meta = {}
             if "tool_call_id" in entry:
                 meta["tool_call_id"] = entry["tool_call_id"]
             chat_dialogue.append(['', '', content, meta])
         elif role in ("system", "developer"):
-            system_message += f"\n{content}" if system_message else content
+            if not seen_non_system:
+                # Leading system messages go to custom_system_message (placed at top)
+                system_message += f"\n{content}" if system_message else content
+            else:
+                # Mid-conversation system messages: preserve position in history
+                if current_message:
+                    chat_dialogue.append([current_message, '', '', {}])
+                    current_message = ""
+                chat_dialogue.append([content, '', '', {"role": "system"}])
 
     if not user_input_last:
         user_input = ""
diff --git a/modules/chat.py b/modules/chat.py
index 5cf550d6..8af92273 100644
--- a/modules/chat.py
+++ b/modules/chat.py
@@ -315,7 +315,10 @@ def generate_chat_prompt(user_input, state, **kwargs):
                         "tool_call_id": item.get('tool_call_id', '')
                     })
 
-        if user_msg not in ['', '<|BEGIN-VISIBLE-CHAT|>']:
+        if entry_meta.get('role') == 'system':
+            if user_msg:
+                messages.insert(insert_pos, {"role": "system", "content": user_msg})
+        elif user_msg not in ['', '<|BEGIN-VISIBLE-CHAT|>']:
             # Check for user message attachments in metadata
             user_key = f"user_{row_idx}"
             enhanced_user_msg = user_msg