diff --git a/tests/tasks/uipath-maestro-flow/_shared/preflight_connections.py b/tests/tasks/uipath-maestro-flow/_shared/preflight_connections.py
new file mode 100644
index 0000000000..99e5ca7132
--- /dev/null
+++ b/tests/tasks/uipath-maestro-flow/_shared/preflight_connections.py
@@ -0,0 +1,77 @@
+#!/usr/bin/env python3
+"""Fail a task as ERROR, not FAILURE, when the tenant connection it needs is down.
+
+Usage:
+    preflight_connections.py <connector-key> [<connector-key> ...]
+
+A `pre_run` failure lands the run as ``FinalStatus.ERROR``; a criterion failure
+lands it as ``FAILURE``. Without this, a revoked grant or an asleep tenant reads
+as an agent mistake:
+
+  skill-flow-outlook-trigger-inbox   AADSTS50173, grant revoked 2026-08-31
+  skill-flow-generic-dynamic-node    ServiceNow developer instance hibernating
+
+Both were scored FAILURE on 2026-09-04 and root-caused as skill defects before
+anyone read far enough into the checker output to find the 403.
+
+Passes when at least one connection for each key reports Enabled. Connections
+live in several folders, so `--all-folders` is required; without it an empty
+result is a false negative.
+"""
+
+from __future__ import annotations
+
+import json
+import subprocess
+import sys
+
+
+def _connections(key: str) -> list[dict]:
+    proc = subprocess.run(
+        ["uip", "is", "connections", "list", key, "--all-folders", "--output", "json"],
+        capture_output=True,
+        text=True,
+        timeout=90,
+    )
+    if proc.returncode != 0:
+        raise RuntimeError(f"`uip is connections list {key}` exited {proc.returncode}: {proc.stderr.strip()}")
+    payload = json.loads(proc.stdout)
+    if payload.get("Result") != "Success":
+        raise RuntimeError(f"connections list for {key} failed: {payload.get('Message', payload)}")
+    return payload.get("Data") or []
+
+
+def main(keys: list[str]) -> int:
+    broken: list[str] = []
+    for key in keys:
+        try:
+            conns = _connections(key)
+        except Exception as exc:  # noqa: BLE001 — any failure here is a blocked tenant
+            broken.append(f"{key}: {exc}")
+            continue
+        if not conns:
+            broken.append(f"{key}: no connection in any folder")
+            continue
+        enabled = [c for c in conns if c.get("State") == "Enabled"]
+        if not enabled:
+            states = ", ".join(f"{c.get('Name')}={c.get('State')}" for c in conns)
+            broken.append(f"{key}: no Enabled connection ({states})")
+            continue
+        print(f"OK: {key} — {len(enabled)}/{len(conns)} connection(s) Enabled")
+
+    if broken:
+        print(
+            "TENANT NOT READY — this is an environment failure, not an agent failure.\n  "
+            + "\n  ".join(broken)
+            + "\n\nReauthorize the connection, or wake the provider instance, then re-run.",
+            file=sys.stderr,
+        )
+        return 1
+    return 0
+
+
+if __name__ == "__main__":
+    if len(sys.argv) < 2:
+        print(__doc__, file=sys.stderr)
+        sys.exit(2)
+    sys.exit(main(sys.argv[1:]))
diff --git a/tests/tasks/uipath-maestro-flow/connector_features/generic_dynamic_node/generic_dynamic_node.yaml b/tests/tasks/uipath-maestro-flow/connector_features/generic_dynamic_node/generic_dynamic_node.yaml
index 23a701a596..9816a70d59 100644
--- a/tests/tasks/uipath-maestro-flow/connector_features/generic_dynamic_node/generic_dynamic_node.yaml
+++ b/tests/tasks/uipath-maestro-flow/connector_features/generic_dynamic_node/generic_dynamic_node.yaml
@@ -52,6 +52,10 @@ initial_prompt: |
   up; only then stop on that field rather than inventing a value. Record every
   decision, assumption, and blocked step in your final response. Instructions in
   the task take precedence over this paragraph.
+pre_run:
+  - command: 'python3 "$SKILLS_REPO_PATH/tests/tasks/uipath-maestro-flow/_shared/preflight_connections.py" uipath-servicenow-servicenow'
+    timeout: 120
+
 success_criteria:
   # ── Flow file validity ─────────────────────────────────────────────────
   - type: run_command
diff --git a/tests/tasks/uipath-maestro-flow/single_node/outlook_trigger_inbox/outlook_trigger_inbox.yaml b/tests/tasks/uipath-maestro-flow/single_node/outlook_trigger_inbox/outlook_trigger_inbox.yaml
index c9bb6ced57..567936b1b4 100644
--- a/tests/tasks/uipath-maestro-flow/single_node/outlook_trigger_inbox/outlook_trigger_inbox.yaml
+++ b/tests/tasks/uipath-maestro-flow/single_node/outlook_trigger_inbox/outlook_trigger_inbox.yaml
@@ -41,6 +41,10 @@ initial_prompt: |
   up; only then stop on that field rather than inventing a value. Record every
   decision, assumption, and blocked step in your final response. Instructions in
   the task take precedence over this paragraph.
+pre_run:
+  - command: 'python3 "$SKILLS_REPO_PATH/tests/tasks/uipath-maestro-flow/_shared/preflight_connections.py" uipath-microsoft-outlook365'
+    timeout: 120
+
 success_criteria:
   # ── Structural: flow builds and validates ──────────────────────────────
   - type: run_command