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Delay the start of your containers with the tailscale dependency. Are you using required or depends_on in your docker-compose.yml
https://hatchjs.com/docker-compose-conditionally-start-service/
If you're using kubernetes you can make the requirements at the pod level
https://stackoverflow.com/questions/69423932/container-initialization-order-in-pod-on-k8s
Edit: If using docker-compose.yml you can set a condition on a healthcheck
You can also specify a condition that must be met before the service is started. For example, the following configuration will start the
web
service only if thedb
service is healthy:The
service_healthy
condition checks the health of thedb
service using thedocker-compose ps
command. If thedb
service is healthy, theweb
service will be started.