Flint 2 Router No VPN after reboot

Here, so you don't have to babysit & to zero in on any outage windows a little better. Note I assume you're putting everything thru the VPN. If not add Cloudflare DNS (or whatever other IP/server you want to ping) to an approp. VPN policy:

mkdir -p /root/.bin/ # make a directory to store the shell script/sh
cat <<- '__EOF' > /root/.bin/pinger
	#!/bin/sh
	# shellcheck shell=sh

	[ -n "$1" ] && TARGET="$1"

	ping -4 -w '2' -q -c '2' "${TARGET}
	ping_status="${?}"
	[ "${ping_status}" = '0' ] || logger -t pinger "Ping to ${TARGET} failed [✘]"

	exit 0

__EOF
chmod +x /root/.bin/pinger # make the sh executable
printf "*/5 * * * * /root/.bin/pinger '1.1.1.1' # ping cloudflare dns every five mins\n" >> /etc/crontabs/root
/etc/init.d/cron restart # restart the system timer to process every 5 min

logread -e 'pinger' will output any failed attempts including the timestamp.

Pro Tip

Update your .profile path to include /root/.bin so you can run it right after logging in via SSH by rand-hostname. See related below.