diff --git a/skills/flight-finder/SKILL.md b/skills/flight-finder/SKILL.md
index 53490c0..0b86bb1 100644
--- a/skills/flight-finder/SKILL.md
+++ b/skills/flight-finder/SKILL.md
@@ -66,6 +66,8 @@ Completion rule:
 - A partial source result is not completion.
 - A partial helper result is not completion.
 - The workflow is complete only when the final report payload exists, the PDF is rendered, the email was sent, and any VPN cleanup required by the run has been attempted.
+- An interim commentary/status line is not completion.
+- For isolated cron-style runs, do not leave the run with only a phase-update summary. If PDF render or email send did not happen, the terminal result must say so explicitly as a failed or incomplete outcome.
 
 ## WhatsApp-safe behavior
 
@@ -80,6 +82,23 @@ Follow the same operational style as `property-assessor`:
 - if PDF render fails, return the completed report summary in chat and report delivery failure separately
 - if email send fails after render, say so clearly and keep the rendered PDF path
 
+## Long-running command rule
+
+- Do not fire a long-running local command and then abandon it.
+- If an `exec` call returns a running session/process handle instead of a completed result, immediately follow it with the relevant process polling/log calls until the command finishes, fails, or times out.
+- Treat VPN connect, fresh search sweeps, PDF render, and Gmail send as critical-path commands. They must be observed to completion; do not assume they succeeded just because the process started.
+- If a critical-path command cannot be observed to completion, stop claiming progress and report the run as incomplete.
+
+## Isolated cron rule
+
+- In isolated cron runs, success means all of the following are true:
+  - fresh search artifacts exist for the current run
+  - final `report-payload.json` exists for the current run
+  - PDF render completed
+  - Gmail send completed to the requested recipient
+- If the model/provider times out, the VPN step flakes, or the run ends before those artifacts exist, report a failure/incomplete outcome rather than an `ok`-sounding completion summary.
+- Do not end an isolated cron run on the VPN/connect phase alone.
+
 ## Search-source contract
 
 Use the proven travel-source order from the local viability findings: