diff --git a/src/headless.ts b/src/headless.ts
index 77d1c3521..83cb013db 100644
--- a/src/headless.ts
+++ b/src/headless.ts
@@ -1901,9 +1901,10 @@ async function runHeadlessOnce(
 	try {
 		await client.init({ clientId: "sf-headless" });
 		_v2Enabled = true;
-	} catch {
+	} catch (initErr) {
+		const reason = initErr instanceof Error ? initErr.message : String(initErr);
 		process.stderr.write(
-			"[headless] Warning: v2 init failed, falling back to v1 string-matching\n",
+			`[headless] Warning: v2 init failed (${reason}), falling back to v1 string-matching\n`,
 		);
 	}