Hello,
Based on the timeout error where the notification never reached the Wazuh Server, you should check the logs directly on the device that is agent id 185. Please look at /var/ossec/logs/ossec.log (on Linux) or C:\Program Files (x86)\ossec-agent\ossec.log (on Windows) for any entries containing "upgrade" or "WPK" to see if the process failed locally.
You should also run /var/ossec/bin/agent_control -i 185 on your manager to verify if the version number actually changed on the device that is agent id 185. It is possible the agent upgraded successfully but simply failed to report back before the timeout. If the version hasn't changed, please confirm the agent is currently in an "Active" state and that no firewalls are blocking port 1514 (agent connection) or port 1515 (enrollment).
If you post the relevant log entries, I can help investigate the issue further.