diff --git a/scripts/lib/upgrade-zulip-stage-2 b/scripts/lib/upgrade-zulip-stage-2
index cb33b222f1..0039ef8be7 100755
--- a/scripts/lib/upgrade-zulip-stage-2
+++ b/scripts/lib/upgrade-zulip-stage-2
@@ -215,7 +215,15 @@ elif args.from_git:
     # update-prod-static with the Git upgrade process.  But it'll fail
     # safely; this seems like a worthwhile tradeoff to minimize downtime.
     logging.info("Building static assets...")
-    subprocess.check_call(["./tools/update-prod-static"], preexec_fn=su_to_zulip)
+    try:
+        subprocess.check_call(["./tools/update-prod-static"], preexec_fn=su_to_zulip)
+    except subprocess.CalledProcessError:
+        logging.error("Failed to build static assets.")
+        if IS_SERVER_UP:
+            logging.error("Usually the cause is insufficient free RAM to run webpack.")
+            logging.error("Try stopping the Zulip server (scripts/stop-server) and trying again.")
+        sys.exit(1)
+
     logging.info("Caching Zulip Git version...")
     subprocess.check_call(["./tools/cache-zulip-git-version"], preexec_fn=su_to_zulip)
 else: