diff --git a/agent/prompt_builder.py b/agent/prompt_builder.py
index 3a6ec2441..1a0ee14bd 100644
--- a/agent/prompt_builder.py
+++ b/agent/prompt_builder.py
@@ -176,6 +176,20 @@ SKILLS_GUIDANCE = (
     "Skills that aren't maintained become liabilities."
 )
 
+CHECKPOINT_GUIDANCE = (
+    "When a CHECKPOINT block appears at session start, read it and resume from "
+    "where the previous session left off. Do not start over — pick up at the "
+    "first in_progress step.\n"
+    "Write a checkpoint (action=\"write\") at these moments:\n"
+    "- Before a risky command that could break state\n"
+    "- After completing a major step in a multi-step task (then action=\"update\" "
+    "for subsequent steps)\n"
+    "- When you have important \"why\" decisions that won't be obvious later\n"
+    "Clear the checkpoint (action=\"clear\") when the task is fully done.\n"
+    "Pre-compression checkpoints are auto-written — you do not need to worry "
+    "about losing progress when the context window fills."
+)
+
 TOOL_USE_ENFORCEMENT_GUIDANCE = (
     "# Tool-use enforcement\n"
     "You MUST use your tools to take action — do not describe what you would do "
diff --git a/run_agent.py b/run_agent.py
index a2a477200..0ba8ad5de 100644
--- a/run_agent.py
+++ b/run_agent.py
@@ -85,6 +85,7 @@ from agent.error_classifier import classify_api_error, FailoverReason
 from agent.prompt_builder import (
     DEFAULT_AGENT_IDENTITY, PLATFORM_HINTS,
     MEMORY_GUIDANCE, SESSION_SEARCH_GUIDANCE, SKILLS_GUIDANCE,
+    CHECKPOINT_GUIDANCE,
     build_nous_subscription_prompt,
 )
 from agent.model_metadata import (
@@ -4396,6 +4397,8 @@ class AIAgent:
             tool_guidance.append(SESSION_SEARCH_GUIDANCE)
         if "skill_manage" in self.valid_tool_names:
             tool_guidance.append(SKILLS_GUIDANCE)
+        if "checkpoint" in self.valid_tool_names:
+            tool_guidance.append(CHECKPOINT_GUIDANCE)
         if tool_guidance:
             prompt_parts.append(" ".join(tool_guidance))