Hi Certain
From what you're describing, this doesn't sound like a simple connectivity issue since both machines are online and discoverable. In my experience, when Remote Assistance immediately fails or reports firewall, service, or security-related errors on Windows 11 Enterprise, the most common cause is a Group Policy restriction, disabled Remote Assistance settings, or required Windows services not running consistently on one or both devices.
I'd start by verifying that Remote Assistance is explicitly enabled on both workstations (System Properties > Remote tab), and then check whether a domain GPO is overriding the local configuration. It's also worth confirming that the Windows Defender Firewall Remote Assistance rules are enabled for the active network profile, as domain policies can silently disable these exceptions. Another thing I would check is the status of services such as Remote Procedure Call (RPC) and related networking services, since Remote Assistance relies heavily on them and access errors can occur even when basic network connectivity is working.
If the devices are domain-joined, reviewing the output of gpresult /h report.html can quickly reveal whether a security policy is blocking Remote Assistance, unsolicited connections, or required firewall rules. Event Viewer is also very helpful here. Check Applications and Services Logs > Microsoft > Windows > RemoteAssistance and the System log for any corresponding errors at the time of the connection attempt.
The fact that the issue occurs on both old and newly deployed systems points more toward an environmental factor such as domain policy, security hardening, or firewall configuration rather than a workstation-specific problem. Once those areas are validated, we can narrow down the root cause much more effectively.
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