diff --git a/cron/scheduler.py b/cron/scheduler.py
index 876000a89..2041411b5 100644
--- a/cron/scheduler.py
+++ b/cron/scheduler.py
@@ -12,6 +12,7 @@ import asyncio
 import concurrent.futures
 import json
 import logging
+import re
 import os
 import subprocess
 import sys
@@ -544,6 +545,55 @@ def _run_job_script(script_path: str) -> tuple[bool, str]:
     except Exception as exc:
         return False, f"Script execution failed: {exc}"
 
+# ---------------------------------------------------------------------------
+# Cloud-context warning for local-service references (#378, #456)
+# ---------------------------------------------------------------------------
+
+_LOCAL_SERVICE_PATTERNS = [
+    re.compile(r'localhost:\d+', re.IGNORECASE),
+    re.compile(r'127\.0\.0\.1:\d+'),
+    re.compile(r'check\s+ollama', re.IGNORECASE),
+    re.compile(r'ollama\s+(is\s+)?respond', re.IGNORECASE),
+    re.compile(r'curl\s+localhost', re.IGNORECASE),
+    re.compile(r'curl\s+127\.', re.IGNORECASE),
+    re.compile(r'curl\s+local', re.IGNORECASE),
+    re.compile(r'ping\s+localhost', re.IGNORECASE),
+    re.compile(r'poll(ing)?\s+local', re.IGNORECASE),
+    re.compile(r'check\s+service\s+respond', re.IGNORECASE),
+    re.compile(r'11434'),  # Ollama default port
+    re.compile(r'11435'),  # common alt Ollama port
+]
+
+
+def _detect_local_service_refs(prompt: str) -> list[str]:
+    """Return list of local-service reference descriptions found in prompt."""
+    refs = []
+    for pat in _LOCAL_SERVICE_PATTERNS:
+        m = pat.search(prompt)
+        if m:
+            refs.append(m.group(0))
+    return refs
+
+
+def _inject_cloud_context(prompt: str, refs: list[str], provider: str) -> str:
+    """Prepend a SYSTEM NOTE so the agent knows it cannot reach localhost."""
+    refs_str = ", ".join(f'"{r}"' for r in refs)
+    warning = (
+        "[SYSTEM NOTE — cloud endpoint]
+"
+        f"You are running on a cloud inference endpoint ({provider}). "
+        f"Your prompt references local services: {refs_str}. "
+        "You CANNOT reach localhost or any local network address from this endpoint. "
+        "Do NOT attempt curl, ping, SSH, or any network calls to localhost. "
+        "Instead, report to the user that this job requires a local model endpoint "
+        "to check local services, and suggest they re-run with a local provider.
+
+"
+    )
+    return warning + prompt
+
+
+
 
 def _build_job_prompt(job: dict) -> str:
     """Build the effective prompt for a cron job, optionally loading one or more skills first."""
@@ -817,6 +867,18 @@ def run_job(job: dict) -> tuple[bool, str, str, Optional[str]]:
                 job_name,
             )
 
+        # Inject cloud-context warning when prompt references local services (#378)
+        if _is_cloud:
+            _local_refs = _detect_local_service_refs(prompt)
+            if _local_refs:
+                _provider_name = turn_route["runtime"].get("provider", "cloud")
+                prompt = _inject_cloud_context(prompt, _local_refs, _provider_name)
+                logger.info(
+                    "Job '%s': injected cloud-context warning for local refs: %s",
+                    job_name,
+                    _local_refs,
+                )
+
         _agent_kwargs = _safe_agent_kwargs({
             "model": turn_route["model"],
             "api_key": turn_route["runtime"].get("api_key"),