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Hello, here is what I'm doing: I creating AWS macOS instance I then set up a /Library/LaunchDaemon plist file that runs a bash script: 	<?xml version="1.0" encoding="UTF-8"?> 	<!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "XXXXX/DTDs/PropertyList-1.0.dtd"> 	<plist version="1.0"> 	<dict> 		<key>Label</key> 		<string>aws-ec2-mac-amis.cloud-connect</string> 		<key>ProgramArguments</key> 		<array> 			<string>/usr/bin/env</string> 			<string>/Users/ec2-user/aws-ec2-mac-amis/cloud-connect.bash</string> 		</array> 		<key>RunAtLoad</key> 		<true/> 		<key>WorkingDirectory</key> 		<string>/Users/ec2-user</string> 		<key>StandardErrorPath</key> 		<string>/var/log/cloud-connect.log</string> 		<key>StandardOutPath</key> 		<string>/var/log/cloud-connect.log</string> 		<key>EnableTransactions</key> 		<true/> 		<key>ExitTimeOut</key> 		<string>300</string> 	</dict> 	</plist> I've tried this same list without EnableTransactions and there is no difference. This works and my bash script runs just fine: #!/bin/bash set -exo pipefail [[ ! $EUID -eq 0 ]] && echo "RUN AS ROOT!" && exit 1 SCRIPT_DIR="$( cd "$( dirname "${BASH_SOURCE[0]}" )" >/dev/null 2>&1 && pwd )" cd $SCRIPT_DIR echo "Waiting for networking..." while ! ping -c 1 -n github.com &> /dev/null; do sleep 1; done git pull . ./_helpers.bash disjoin() { 	set -x 	/usr/local/bin/ankacluster disjoin & 	CERTS="" 	[[ ! -z "$CLOUD_CONNECT_CERT" ]] && CERTS="--cert $CLOUD_CONNECT_CERT" 	[[ ! -z "$CLOUD_CONNECT_KEY" ]] && CERTS="$CERTS --cert-key $CLOUD_CONNECT_KEY" 	[[ ! -z "$CLOUD_CONNECT_CA" ]] && CERTS="$CERTS --cacert $CLOUD_CONNECT_CA" 	NODE_ID="$(curl -s $CERTS "${ANKA_CONTROLLER_ADDRESS}/api/v1/node" | jq -r ".body | .[] | select(.node_name==\"$(hostname)\") | .node_id")" 	curl -s $CERTS -X DELETE "${ANKA_CONTROLLER_ADDRESS}/api/v1/node" -H "Content-Type: application/json" -d "{\"node_id\": \"$NODE_ID\"}" } Grab the ENVS the user sets in user-data if [[ ! -e $CLOUD_CONNECT_PLIST_PATH ]]; then 	mkdir -p $LAUNCH_LOCATION cat > $CLOUD_CONNECT_PLIST_PATH <<EOD 	<?xml version="1.0" encoding="UTF-8"?> 	<!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd"> 	<plist version="1.0"> 	<dict> 		<key>Label</key> 		<string>aws-ec2-mac-amis.cloud-connect</string> 		<key>ProgramArguments</key> 		<array> 			<string>/usr/bin/env</string> 			<string>/Users/ec2-user/aws-ec2-mac-amis/cloud-connect.bash</string> 		</array> 		<key>RunAtLoad</key> 		<true/> 		<key>WorkingDirectory</key> 		<string>/Users/ec2-user</string> 		<key>StandardErrorPath</key> 		<string>/var/log/cloud-connect.log</string> 		<key>StandardOutPath</key> 		<string>/var/log/cloud-connect.log</string> 		<key>EnableTransactions</key> 		<true/> 		<key>ExitTimeOut</key> 		<string>300</string> 	</dict> 	</plist> EOD 	launchctl load -w $CLOUD_CONNECT_PLIST_PATH else 	echo "$(date) ($(whoami)): Attempting join..." 	Check if user-data exists 	[[ ! -z "$(curl -s XXXX/latest/user-data | grep 404)" ]] && echo "Could not find required ANKA_CONTROLLER_ADDRESS in instance user-data!" && exit 1 	create user ENVs for this session 	$(curl -s XXXX/latest/user-data | sed 's/\"//g') 	IF the user wants to change the IP address for the registry domain name (if they want to use a second EC2 registry for better speed), handle setting the /etc/hosts 	if [[ ! -z "$ANKA_REGISTRY_OVERRIDE_IP" && ! -z "$ANKA_REGISTRY_OVERRIDE_DOMAIN" ]]; then 			modify_hosts $ANKA_REGISTRY_OVERRIDE_DOMAIN $ANKA_REGISTRY_OVERRIDE_IP 	fi 	Ensure that anytime the script stops, we disjoin first 	/usr/local/bin/ankacluster join $ANKA_CONTROLLER_ADDRESS $ANKA_JOIN_ARGS 	trap disjoin 0 Disjoin after we joined properly to avoid unloading prematurely 	set +x 	while true; do 		sleep 1 & 		wait $! 	done fi I see the process running, and the host has connected to the remote server's controller: root						46851	 0.0	0.0	4283172	 1120	 ??	Ss		8:49PM	 0:00.09 /bin/bash /Users/ec2-user/aws-ec2-mac-amis/cloudconnect.bash However, when I terminate the AWS instance, the process stays running and the bash script's trap is never attempted (at least according to the logs). This could very well be an AWS specific issue, however, I wanted to check here and see if I was potentially missing something important. Some things that do work: I can sudo shutdown -r now inside of the host and it disjoins properly before the host shuts down. I can sudo launchctl -w unload inside of the host and it disjoins properly, too.