diff --git a/nanobot/agent/loop.py b/nanobot/agent/loop.py
index 6fe37e9..6cd8e56 100644
--- a/nanobot/agent/loop.py
+++ b/nanobot/agent/loop.py
@@ -224,6 +224,12 @@ class AgentLoop:
                     )
             else:
                 clean = self._strip_think(response.content)
+                # Don't persist error responses to session history — they can
+                # poison the context and cause permanent 400 loops (#1303).
+                if response.finish_reason == "error":
+                    logger.error("LLM returned error: {}", (clean or "")[:200])
+                    final_content = clean or "Sorry, I encountered an error calling the AI model."
+                    break
                 messages = self.context.add_assistant_message(
                     messages, clean, reasoning_content=response.reasoning_content,
                 )
diff --git a/nanobot/providers/base.py b/nanobot/providers/base.py
index eb1599a..f52a951 100644
--- a/nanobot/providers/base.py
+++ b/nanobot/providers/base.py
@@ -51,6 +51,14 @@ class LLMProvider(ABC):
         for msg in messages:
             content = msg.get("content")
 
+            # None content on a plain assistant message (no tool_calls) crashes
+            # providers with "invalid message content type: <nil>".
+            if content is None and msg.get("role") == "assistant" and not msg.get("tool_calls"):
+                clean = dict(msg)
+                clean["content"] = "(empty)"
+                result.append(clean)
+                continue
+
             if isinstance(content, str) and not content:
                 clean = dict(msg)
                 clean["content"] = None if (msg.get("role") == "assistant" and msg.get("tool_calls")) else "(empty)"