diff --git a/scripts/run.ts b/scripts/run.ts
index f1572fc..45e5bf2 100644
--- a/scripts/run.ts
+++ b/scripts/run.ts
@@ -93,6 +93,17 @@ async function main(): Promise<void> {
   if (positionals.length < 1) { printUsage(); process.exit(1); }
 
   const command = positionals[0] as Command;
+
+  // Resolve session ID: explicit CLI arg > env > auto-generate structured ID
+  const sessionId = process.env.SKILL_SESSION_ID || (() => {
+    const ts = new Date();
+    const pad = (n: number) => String(n).padStart(2, '0');
+    const tsPart = `${ts.getFullYear()}${pad(ts.getMonth()+1)}${pad(ts.getDate())}-${pad(ts.getHours())}${pad(ts.getMinutes())}${pad(ts.getSeconds())}`;
+    const rand = Math.random().toString(36).slice(2, 6);
+    return `vps-${tsPart}-${rand}`;
+  })();
+  process.env.SKILL_SESSION_ID = sessionId;
+
   const startMs = Date.now();
   let result: Awaited<ReturnType<typeof run>>;
 
@@ -100,13 +111,14 @@ async function main(): Promise<void> {
     result = await run(command, positionals.slice(1), dryRun);
   } catch (err) {
     const error = err instanceof Error ? err.message : String(err);
-    console.log(JSON.stringify({ status: 'failed', command, dryRun, error }, null, 2));
-    if (!dryRun) reportTelemetry({ skill: SKILL_NAME, command, status: 'failed', durationMs: Date.now() - startMs, error });
+    console.log(JSON.stringify({ status: 'failed', command, dryRun, sessionId, error }, null, 2));
+    if (!dryRun) reportTelemetry({ skill: SKILL_NAME, command, sessionId, status: 'failed', durationMs: Date.now() - startMs, error });
     process.exit(1);
   }
 
-  console.log(JSON.stringify(result, null, 2));
-  if (!dryRun) reportTelemetry({ skill: SKILL_NAME, command, status: result.status, durationMs: Date.now() - startMs, error: (result as any).error });
+  const output = { ...result, sessionId } as Record<string, unknown>;
+  console.log(JSON.stringify(output, null, 2));
+  if (!dryRun) reportTelemetry({ skill: SKILL_NAME, command, sessionId, status: result.status, durationMs: Date.now() - startMs, error: (result as any).error });
 }
 
 main().catch((err) => {