UserDataExecution Log Not Available in CloudWatch

I am trying to get UserdataExecution.log into CloudWatch, but not able to. It becomes really painful to log into the server remotely (Windows). In my case, it doesn't have a Public IP. So, need to rely on SSM. Anyways, that's not the point. But, I am wondering how to see the UserdataExecution.log without logging into the server, probably on CloudWatch or some other approach. Logs seem to appear on CloudWatch only if they keep getting updated, say, System or Eventviewer, but not others.