diff --git a/strix/agents/base_agent.py b/strix/agents/base_agent.py
index ed793db..72f51a5 100644
--- a/strix/agents/base_agent.py
+++ b/strix/agents/base_agent.py
@@ -173,6 +173,33 @@ class BaseAgent(metaclass=AgentMeta):
 
             self.state.increment_iteration()
 
+            if (
+                self.state.is_approaching_max_iterations()
+                and not self.state.max_iterations_warning_sent
+            ):
+                self.state.max_iterations_warning_sent = True
+                remaining = self.state.max_iterations - self.state.iteration
+                warning_msg = (
+                    f"URGENT: You are approaching the maximum iteration limit. "
+                    f"Current: {self.state.iteration}/{self.state.max_iterations} "
+                    f"({remaining} iterations remaining). "
+                    f"Please prioritize completing your required task(s) and calling "
+                    f"the appropriate finish tool (finish_scan for root agent, "
+                    f"agent_finish for sub-agents) as soon as possible."
+                )
+                self.state.add_message("user", warning_msg)
+
+            if self.state.iteration == self.state.max_iterations - 3:
+                final_warning_msg = (
+                    "CRITICAL: You have only 3 iterations left! "
+                    "Your next message MUST be the tool call to the appropriate "
+                    "finish tool: finish_scan if you are the root agent, or "
+                    "agent_finish if you are a sub-agent. "
+                    "No other actions should be taken except finishing your work "
+                    "immediately."
+                )
+                self.state.add_message("user", final_warning_msg)
+
             try:
                 should_finish = await self._process_iteration(tracer)
                 if should_finish:
diff --git a/strix/agents/state.py b/strix/agents/state.py
index 304c2ee..6273757 100644
--- a/strix/agents/state.py
+++ b/strix/agents/state.py
@@ -26,6 +26,7 @@ class AgentState(BaseModel):
     llm_failed: bool = False
     waiting_start_time: datetime | None = None
     final_result: dict[str, Any] | None = None
+    max_iterations_warning_sent: bool = False
 
     messages: list[dict[str, Any]] = Field(default_factory=list)
     context: dict[str, Any] = Field(default_factory=dict)
@@ -106,6 +107,9 @@ class AgentState(BaseModel):
     def has_reached_max_iterations(self) -> bool:
         return self.iteration >= self.max_iterations
 
+    def is_approaching_max_iterations(self, threshold: float = 0.85) -> bool:
+        return self.iteration >= int(self.max_iterations * threshold)
+
     def has_waiting_timeout(self) -> bool:
         if not self.waiting_for_input or not self.waiting_start_time:
             return False