Hi @Gareth Morrallee
Welcome to Microsoft Q&A, Thanks for asking question here!
The error with the MMA connecting to the Log Analytics Workspace likely a TLS handshake issue caused by a mismatch in encryption protocol please try with below steps:
1.Make sure both the client and server support TLS 1.2 and verify if it's enabled on the server by checking the Windows Registry.
2.The error suggests a cipher suite mismatch, so ensure your server has the necessary TLS 1.2 cipher suites enabled and update the server's configuration if needed.
3.If hardening policies disable lower TLS versions, you may need to adjust registry entries to allow TLS 1.2 connections.
Add or ensure the following registry keys exist:
[HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Client]
"Disabled"=dword:00000000
"Enabled"=dword:00000001
4.Even if port 443 is open, make sure there are no proxy settings blocking SSL/TLS connections, and configure the SSL inspection proxy to bypass traffic for Azure endpoints if needed.
5.Check for issues with the certificates used by MMA, remove any outdated or invalid certificates, and generate a new one by restarting the MMA service.
6.Check the event logs for the MMA service to find specific error messages that may explain the connection issue.
Reference documents: https://stackoverflow.com/questions/67297713/azure-log-analytics-agentmicrosoft-monitoring-agent-installation-error-error
https://learn.microsoft.com/en-us/services-hub/unified/health/troubleshooting-mma-agent
https://learn.microsoft.com/en-us/azure/azure-monitor/agents/agent-windows-troubleshoot?tabs=UpdateMMA
https://learn.microsoft.com/en-us/answers/questions/1141299/azure-migrate-service-mma-installation-issue-on-ano
Please let me know if you required anything!