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It looks like this is happening on one instance based on your question so it is most likely a Windows operating system issue. Can you try to connect to the instance via RDP and check for updates manually in the Windows Update GUI either in Settings or Control Panel depending on the version of Windows? If that fails or results in any errors, SSM will not be able to check for updates either because it relies on Windows Update functionality within Windows to do this. If Windows Update is not working, open a support case with Microsoft or search online for troubleshooting steps. Alternatively, it may be faster and simpler to launch a new EC2 instance and migrate any applications and data to it compared to troubleshooting a potentially complex and time-consuming operating system problem.
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