I have exactly the same issue here as well. I have confirmed my clocks are correct and synchronized with ntp. The jenkins master just gives up trying to contact the slave, the slave as a result is orphaned, in running state and reachable via SSH from the jenkins master. I am using a VPC peer in AWS. The Jenkins master is in an AWS "infrastructure" account.
com.amazonaws.services.ec2.model.AmazonEC2Exception: Request has expired.
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