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Hello,
The step "waituntilinstancessmmanaged" is to check if the instance is reporting with an "Online" Status to the SSM service or not. If it does not report online status, then the check will timeout and fail.
Hence please refer to the below document to check if the instance is having necessary IAM role attached, network connectivity to SSM endpoint and SSM agent installed.
https://repost.aws/knowledge-center/systems-manager-ec2-instance-not-appear
I am also facing the same problem. Its windows agent and its taking time to launch and automation service is timeout before even the ec2 comes online with all checks.. and i cant edit the timeout of 240s
I've gone through this over the last day, basically, it boils down to having the instance running on the same subnet as that of the domain controller, which is most probably running on a private subnet. Since I have not setup the private subnet to have a NAT gateway, it's unable to communicate to the external web which SSM is by default set into.
To do the change, I copied the "AWS-CreateDSManagementInstance" run book, and modified the subnet on the "LaunchInstance" and "LaunchInstanceNoKey" actions to have the value of the public subnet I want it to be launched in. Took me a while to realize that there's a different run for the LaunchInstanceNoKey so you need to modify that too.
Oh, and if you don't have auto-assign public IP enabled, you need to assign an elastic IP just as the instance is launching. :)
