diff --git a/src/cai/cli.py b/src/cai/cli.py
index c1694c7c..fde1c5be 100644
--- a/src/cai/cli.py
+++ b/src/cai/cli.py
@@ -1613,7 +1613,16 @@ def run_cai_cli(
                         asyncio.run(process_streamed_response(agent, conversation_input))
                     except ContextCompactedError:
                         # Auto-compact fired mid-runner; restart with fresh context.
-                        _post_compact_input = _last_user_input or "Continue the current task."
+                        _base = _last_user_input or "Continue the current task."
+                        _post_compact_input = (
+                            f"{_base}\n\n"
+                            "IMPORTANT: Your context window was just compacted. "
+                            "Your session memory is already loaded above. "
+                            "Review the 'Exhausted Approaches' section in your memory and "
+                            "DO NOT repeat any technique, command, URL, port scan, or login "
+                            "attempt already listed there. "
+                            "Pick up exactly where you left off using only NEW approaches."
+                        )
                         from cai.sdk.agents.simple_agent_manager import AGENT_MANAGER as _AM
                         _reloaded = _AM.get_active_agent()
                         if _reloaded is not None:
@@ -1683,7 +1692,16 @@ def run_cai_cli(
                         response = asyncio.run(Runner.run(agent, conversation_input))
                     except ContextCompactedError:
                         # Auto-compact fired mid-runner; restart with fresh context.
-                        _post_compact_input = _last_user_input or "Continue the current task."
+                        _base = _last_user_input or "Continue the current task."
+                        _post_compact_input = (
+                            f"{_base}\n\n"
+                            "IMPORTANT: Your context window was just compacted. "
+                            "Your session memory is already loaded above. "
+                            "Review the 'Exhausted Approaches' section in your memory and "
+                            "DO NOT repeat any technique, command, URL, port scan, or login "
+                            "attempt already listed there. "
+                            "Pick up exactly where you left off using only NEW approaches."
+                        )
                         from cai.sdk.agents.simple_agent_manager import AGENT_MANAGER as _AM
                         _reloaded = _AM.get_active_agent()
                         if _reloaded is not None:
diff --git a/src/cai/repl/commands/memory.py b/src/cai/repl/commands/memory.py
index f2e283c8..0e1af02b 100644
--- a/src/cai/repl/commands/memory.py
+++ b/src/cai/repl/commands/memory.py
@@ -1267,39 +1267,60 @@ This session is being continued from a previous conversation that ran out of con
             return None
     
     def _format_history_for_summary(self, history: List[Dict[str, Any]]) -> str:
-        """Format message history for summarization."""
+        """Format message history for summarization.
+
+        Critical design goals:
+        - Include EVERY tool call with its exact arguments (commands run, URLs visited,
+          ports scanned) so the summary model can produce an "Exhausted Approaches" list.
+        - Include enough of each tool result to convey success/failure and key findings.
+        - Avoid blowing out the summary model's context by capping large outputs.
+        """
+        TOOL_OUTPUT_KEEP = 2000   # chars to preserve from each tool result
+        MAX_PARTS       = 200     # maximum formatted blocks to pass (covers ~100 turns)
+
         formatted_parts = []
-        
+
         for msg in history:
             role = msg.get("role", "unknown")
             content = msg.get("content", "")
-            
-            # Skip empty messages
-            if not content:
-                continue
-                
-            # Format based on role
+
             if role == "user":
-                formatted_parts.append(f"USER: {content}")
+                if content:
+                    formatted_parts.append(f"USER: {content}")
+
             elif role == "assistant":
-                # Check for tool calls
-                if "tool_calls" in msg and msg["tool_calls"]:
+                # -- tool calls: extract args from both dict-style and object-style entries --
+                tool_calls = msg.get("tool_calls") or []
+                if tool_calls:
                     tool_info = []
-                    for tc in msg["tool_calls"]:
-                        if hasattr(tc, "function"):
-                            tool_info.append(f"{tc.function.name}({tc.function.arguments})")
+                    for tc in tool_calls:
+                        if isinstance(tc, dict):
+                            fn = tc.get("function", {})
+                            name = fn.get("name", "?")
+                            args = fn.get("arguments", "")
+                            tool_info.append(f"{name}({args})")
+                        elif hasattr(tc, "function"):
+                            tool_info.append(
+                                f"{tc.function.name}({tc.function.arguments})"
+                            )
                     if tool_info:
-                        formatted_parts.append(f"ASSISTANT (tools): {', '.join(tool_info)}")
+                        formatted_parts.append(
+                            f"ASSISTANT called tools: {', '.join(tool_info)}"
+                        )
                 if content:
                     formatted_parts.append(f"ASSISTANT: {content}")
+
             elif role == "tool":
-                # Include important tool outputs
-                if len(str(content)) < 500:  # Only include short outputs
-                    formatted_parts.append(f"TOOL OUTPUT: {content}")
+                raw = str(content) if content else ""
+                if len(raw) <= TOOL_OUTPUT_KEEP:
+                    formatted_parts.append(f"TOOL OUTPUT:\n{raw}")
                 else:
-                    formatted_parts.append(f"TOOL OUTPUT: [Long output truncated]")
-                    
-        return "\n\n".join(formatted_parts[-50:])  # Limit to last 50 exchanges
+                    head = raw[:TOOL_OUTPUT_KEEP]
+                    formatted_parts.append(
+                        f"TOOL OUTPUT (truncated to {TOOL_OUTPUT_KEEP} chars):\n{head}\n[...truncated]"
+                    )
+
+        return "\n\n".join(formatted_parts[-MAX_PARTS:])
     
     def _get_current_agent_name(self) -> Optional[str]:
         """Get the name of the current active agent."""