diff --git a/nanobot/providers/litellm_provider.py b/nanobot/providers/litellm_provider.py
index d14e4c0..20c3d25 100644
--- a/nanobot/providers/litellm_provider.py
+++ b/nanobot/providers/litellm_provider.py
@@ -129,24 +129,40 @@ class LiteLLMProvider(LLMProvider):
         messages: list[dict[str, Any]],
         tools: list[dict[str, Any]] | None,
     ) -> tuple[list[dict[str, Any]], list[dict[str, Any]] | None]:
-        """Return copies of messages and tools with cache_control injected."""
-        new_messages = []
-        for msg in messages:
-            if msg.get("role") == "system":
-                content = msg["content"]
-                if isinstance(content, str):
-                    new_content = [{"type": "text", "text": content, "cache_control": {"type": "ephemeral"}}]
-                else:
-                    new_content = list(content)
-                    new_content[-1] = {**new_content[-1], "cache_control": {"type": "ephemeral"}}
-                new_messages.append({**msg, "content": new_content})
-            else:
-                new_messages.append(msg)
+        """Return copies of messages and tools with cache_control injected.
+
+        Two breakpoints are placed:
+        1. System message — caches the static system prompt
+        2. Second-to-last message — caches the conversation history prefix
+        This maximises cache hits across multi-turn conversations.
+        """
+        cache_marker = {"type": "ephemeral"}
+        new_messages = list(messages)
+
+        def _mark(msg: dict[str, Any]) -> dict[str, Any]:
+            content = msg.get("content")
+            if isinstance(content, str):
+                return {**msg, "content": [
+                    {"type": "text", "text": content, "cache_control": cache_marker}
+                ]}
+            elif isinstance(content, list) and content:
+                new_content = list(content)
+                new_content[-1] = {**new_content[-1], "cache_control": cache_marker}
+                return {**msg, "content": new_content}
+            return msg
+
+        # Breakpoint 1: system message
+        if new_messages and new_messages[0].get("role") == "system":
+            new_messages[0] = _mark(new_messages[0])
+
+        # Breakpoint 2: second-to-last message (caches conversation history prefix)
+        if len(new_messages) >= 3:
+            new_messages[-2] = _mark(new_messages[-2])
 
         new_tools = tools
         if tools:
             new_tools = list(tools)
-            new_tools[-1] = {**new_tools[-1], "cache_control": {"type": "ephemeral"}}
+            new_tools[-1] = {**new_tools[-1], "cache_control": cache_marker}
 
         return new_messages, new_tools