diff --git a/cron/scheduler.py b/cron/scheduler.py
index e6db77c09..b6c2dad43 100644
--- a/cron/scheduler.py
+++ b/cron/scheduler.py
@@ -596,6 +596,41 @@ def run_job(job: dict) -> tuple[bool, str, str, Optional[str]]:
     origin = _resolve_origin(job)
     _cron_session_id = f"cron_{job_id}_{_hermes_now().strftime('%Y%m%d_%H%M%S')}"
 
+    # Check for checkpoint from previous timeout — resume where we left off
+    try:
+        _checkpoint_dir = _hermes_home / "cron" / "checkpoints"
+        _checkpoint_path = _checkpoint_dir / f"{job_id}.json"
+        if _checkpoint_path.exists():
+            import json as _json
+            _cp = _json.loads(_checkpoint_path.read_text())
+            _cp_age = (_hermes_now() - _parse_dt(_cp["saved_at"])).total_seconds() if _cp.get("saved_at") else 9999
+            if _cp_age < 7200:  # Only resume if checkpoint is <2 hours old
+                _cp_context = (
+                    f"\n\n[CHECKPOINT: This job timed out previously. "
+                    f"Iterations completed: {_cp.get('iterations_completed', '?')}. "
+                    f"Last activity: {_cp.get('last_activity', '?')}. "
+                    f"Continue from where you left off. Do not repeat work already done.]\n"
+                )
+                # Add last conversation context if available
+                _conv = _cp.get("conversation_history", [])
+                if _conv:
+                    _cp_context += "\n[Previous work summary from last run:]\n"
+                    for _msg in _conv[-5:]:
+                        _role = _msg.get("role", "?")
+                        _content = str(_msg.get("content", ""))[:300]
+                        if _role in ("assistant", "tool"):
+                            _cp_context += f"  {_role}: {_content}\n"
+                prompt = prompt + _cp_context
+                logger.info("Job '%s': resuming from checkpoint (%.0fs old, %d iterations)",
+                           job_id, _cp_age, _cp.get("iterations_completed", 0))
+                # Clear the checkpoint — we're resuming it now
+                _checkpoint_path.unlink()
+            else:
+                logger.info("Job '%s': checkpoint too old (%.0fs), starting fresh", job_id, _cp_age)
+                _checkpoint_path.unlink()
+    except Exception as _cp_err:
+        logger.debug("Job '%s': checkpoint resume failed: %s", job_id, _cp_err)
+
     logger.info("Running job '%s' (ID: %s)", job_name, job_id)
     logger.info("Prompt: %s", prompt[:100])
 
@@ -762,7 +797,7 @@ def run_job(job: dict) -> tuple[bool, str, str, Optional[str]]:
         #
         # Uses the agent's built-in activity tracker (updated by
         # _touch_activity() on every tool call, API call, and stream delta).
-        _cron_timeout = float(os.getenv("HERMES_CRON_TIMEOUT", 600))
+        _cron_timeout = float(os.getenv("HERMES_CRON_TIMEOUT", 900))
         _cron_inactivity_limit = _cron_timeout if _cron_timeout > 0 else None
         _POLL_INTERVAL = 5.0
         _cron_pool = concurrent.futures.ThreadPoolExecutor(max_workers=1)
@@ -812,6 +847,30 @@ def run_job(job: dict) -> tuple[bool, str, str, Optional[str]]:
             _iter_n = _activity.get("api_call_count", 0)
             _iter_max = _activity.get("max_iterations", 0)
 
+            # Save checkpoint before killing — next run can resume
+            try:
+                _checkpoint_dir = _hermes_home / "cron" / "checkpoints"
+                _checkpoint_dir.mkdir(parents=True, exist_ok=True)
+                _checkpoint_path = _checkpoint_dir / f"{job_id}.json"
+                _conv_history = []
+                if hasattr(agent, "conversation_history"):
+                    _conv_history = agent.conversation_history
+                elif hasattr(agent, "_session_messages"):
+                    _conv_history = agent._session_messages
+                _checkpoint = {
+                    "job_id": job_id,
+                    "job_name": job_name,
+                    "saved_at": _hermes_now().isoformat(),
+                    "iterations_completed": _iter_n,
+                    "last_activity": _last_desc,
+                    "conversation_history": _conv_history[-20:] if _conv_history else [],
+                }
+                import json as _json
+                _checkpoint_path.write_text(_json.dumps(_checkpoint, indent=2, default=str))
+                logger.info("Job '%s': checkpoint saved (%d iterations)", job_id, _iter_n)
+            except Exception as _cp_err:
+                logger.warning("Job '%s': failed to save checkpoint: %s", job_id, _cp_err)
+
             logger.error(
                 "Job '%s' idle for %.0fs (inactivity limit %.0fs) "
                 "| last_activity=%s | iteration=%s/%s | tool=%s",
diff --git a/tools/code_execution_tool.py b/tools/code_execution_tool.py
index 0eb1cd2e4..b1d3c059c 100644
--- a/tools/code_execution_tool.py
+++ b/tools/code_execution_tool.py
@@ -33,6 +33,7 @@ import json
 import logging
 import os
 import platform
+import re
 import shlex
 import signal
 import socket