I would suggest using fly logs to tail the logs of the application; you can filter by instance as well, fly logs -i <INSTANCE_IDENTIFIER> (where the instance identifier is the machine id for the cron process group, you can get it with fly machines list). Then on another terminal, fly machine restart <INSTANCE_IDENTIFIER>. When it restarts, if there’s any errors starting supercronic you will get some details as to what happened.
That said, I think the presence of ENTRYPOINT is overriding your specified command for supercronic. You may have some luck changing from ENTRYPOINT to CMD so the command can be overridden by your process group’s commands.
2023-09-07T23:44:11Z app[xxx] nrt [info][ 0.040036] PCI: Fatal: No config space access function found
2023-09-07T23:44:11Z app[xxx] nrt [info] INFO Starting init (commit: 5293a085)...
2023-09-07T23:44:11Z app[xxx] nrt [info] INFO starting statics vsock server
2023-09-07T23:44:11Z app[xxx] nrt [info] INFO Preparing to run: `/rails/bin/docker-entrypoint supercronic /rails/crontab` as rails
2023-09-07T23:44:11Z app[xxx] nrt [info] INFO [fly api proxy] listening at /.fly/api
2023-09-07T23:44:11Z app[xxx] nrt [info]2023/09/07 23:44:11 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:11Z app[xxx] nrt [info]/rails/bin/docker-entrypoint: line 5: exec: supercronic: not found
2023-09-07T23:44:12Z app[xxx] nrt [info] INFO Main child exited normally with code: 127
2023-09-07T23:44:12Z app[xxx] nrt [info] INFO Starting clean up.
2023-09-07T23:44:12Z app[xxx] nrt [info] WARN hallpass exited, pid: 256, status: signal: 15 (SIGTERM)
2023-09-07T23:44:12Z app[xxx] nrt [info]2023/09/07 23:44:12 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:13Z app[xxx] nrt [info][ 2.291358] reboot: Restarting system
2023-09-07T23:44:13Z runner[xxx] nrt [info]machine did not have a restart policy, defaulting to restart
2023-09-07T23:44:13Z app[xxx] nrt [info][ 0.039013] PCI: Fatal: No config space access function found
2023-09-07T23:44:13Z app[xxx] nrt [info] INFO Starting init (commit: 5293a05)...
2023-09-07T23:44:13Z app[xxx] nrt [info] INFO starting statics vsock server
2023-09-07T23:44:13Z app[xxx] nrt [info] INFO Preparing to run: `/rails/bin/docker-entrypoint supercronic /rails/crontab` as rails
2023-09-07T23:44:13Z app[xxx] nrt [info] INFO [fly api proxy] listening at /.fly/api
2023-09-07T23:44:13Z app[xxx] nrt [info]2023/09/07 23:44:13 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:13Z app[xxx] nrt [info]/rails/bin/docker-entrypoint: line 5: exec: supercronic: not found
2023-09-07T23:44:14Z app[xxx] nrt [info] INFO Main child exited normally with code: 127
2023-09-07T23:44:14Z app[xxx] nrt [info] INFO Starting clean up.
2023-09-07T23:44:14Z app[xxx] nrt [info] WARN hallpass exited, pid: 256, status: signal: 15 (SIGTERM)
2023-09-07T23:44:14Z app[xxx] nrt [info]2023/09/07 23:44:14 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:15Z app[xxx] nrt [info][ 2.289442] reboot: Restarting system
2023-09-07T23:44:16Z runner[xxx] nrt [info]machine did not have a restart policy, defaulting to restart
2023-09-07T23:44:16Z app[xxx] nrt [info][ 0.036046] PCI: Fatal: No config space access function found
2023-09-07T23:44:16Z app[xxx] nrt [info] INFO Starting init (commit: 5293a085)...
2023-09-07T23:44:16Z app[xxx] nrt [info] INFO starting statics vsock server
2023-09-07T23:44:16Z app[xxx] nrt [info] INFO Preparing to run: `/rails/bin/docker-entrypoint supercronic /rails/crontab` as rails
2023-09-07T23:44:16Z app[xxx] nrt [info] INFO [fly api proxy] listening at /.fly/api
2023-09-07T23:44:16Z app[xxx] nrt [info]2023/09/07 23:44:16 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:16Z app[xxx] nrt [info]/rails/bin/docker-entrypoint: line 5: exec: supercronic: not found
2023-09-07T23:44:17Z app[xxx] nrt [info] INFO Main child exited normally with code: 127
2023-09-07T23:44:17Z app[xxx] nrt [info] INFO Starting clean up.
2023-09-07T23:44:17Z app[xxx] nrt [info] WARN hallpass exited, pid: 256, status: signal: 15 (SIGTERM)
2023-09-07T23:44:17Z app[xxx] nrt [info]2023/09/07 23:44:17 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:18Z app[xxx] nrt [info][ 2.287433] reboot: Restarting system
2023-09-07T23:44:18Z runner[xxx] nrt [info]machine did not have a restart policy, defaulting to restart
2023-09-07T23:44:19Z app[xxx] nrt [info][ 0.041259] PCI: Fatal: No config space access function found
2023-09-07T23:44:19Z app[xxx] nrt [info] INFO Starting init (commit: 5293a085)...
2023-09-07T23:44:19Z app[xxx] nrt [info] INFO starting statics vsock server
2023-09-07T23:44:19Z app[xxx] nrt [info] INFO Preparing to run: `/rails/bin/docker-entrypoint supercronic /rails/crontab` as rails
2023-09-07T23:44:19Z app[xxx] nrt [info] INFO [fly api proxy] listening at /.fly/api
2023-09-07T23:44:19Z app[xxx] nrt [info]2023/09/07 23:44:19 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:19Z app[xxx] nrt [info]/rails/bin/docker-entrypoint: line 5: exec: supercronic: not found
2023-09-07T23:44:20Z app[xxx] nrt [info] INFO Main child exited normally with code: 127
2023-09-07T23:44:20Z app[xxx] nrt [info] INFO Starting clean up.
2023-09-07T23:44:20Z app[xxx] nrt [info] WARN hallpass exited, pid: 256, status: signal: 15 (SIGTERM)
2023-09-07T23:44:20Z app[xxx] nrt [info]2023/09/07 23:44:20 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:21Z app[xxx] nrt [info][ 2.295553] reboot: Restarting system
2023-09-07T23:44:21Z runner[xxx] nrt [info]machine did not have a restart policy, defaulting to restart
2023-09-07T23:44:22Z app[xxx] nrt [info][ 0.037542] PCI: Fatal: No config space access function found
2023-09-07T23:44:22Z app[xxx] nrt [info] INFO Starting init (commit: 5293a085)...
2023-09-07T23:44:22Z app[xxx] nrt [info] INFO starting statics vsock server
2023-09-07T23:44:22Z app[xxx] nrt [info] INFO Preparing to run: `/rails/bin/docker-entrypoint supercronic /rails/crontab` as rails
2023-09-07T23:44:22Z app[xxx] nrt [info] INFO [fly api proxy] listening at /.fly/api
2023-09-07T23:44:22Z app[xxx] nrt [info]2023/09/07 23:44:22 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:22Z app[xxx] nrt [info]/rails/bin/docker-entrypoint: line 5: exec: supercronic: not found
2023-09-07T23:44:23Z app[xxx] nrt [info] INFO Main child exited normally with code: 127
2023-09-07T23:44:23Z app[xxx] nrt [info] INFO Starting clean up.
2023-09-07T23:44:23Z app[xxx] nrt [info] WARN hallpass exited, pid: 256, status: signal: 15 (SIGTERM)
2023-09-07T23:44:23Z app[xxx] nrt [info]2023/09/07 23:44:23 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:24Z app[xxx] nrt [info][ 2.292225] reboot: Restarting system
2023-09-07T23:44:25Z runner[xxx] nrt [info]machine did not have a restart policy, defaulting to restart
2023-09-07T23:44:26Z app[xxx] nrt [info][ 0.035949] PCI: Fatal: No config space access function found
2023-09-07T23:44:26Z app[xxx] nrt [info] INFO Starting init (commit: 5293a085)...
2023-09-07T23:44:26Z app[xxx] nrt [info] INFO starting statics vsock server
2023-09-07T23:44:26Z app[xxx] nrt [info] INFO Preparing to run: `/rails/bin/docker-entrypoint supercronic /rails/crontab` as rails
2023-09-07T23:44:26Z app[xxx] nrt [info] INFO [fly api proxy] listening at /.fly/api
2023-09-07T23:44:26Z app[xxx] nrt [info]2023/09/07 23:44:26 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:26Z app[xxx] nrt [info]/rails/bin/docker-entrypoint: line 5: exec: supercronic: not found
2023-09-07T23:44:27Z app[xxx] nrt [info] INFO Main child exited normally with code: 127
2023-09-07T23:44:27Z app[xxx] nrt [info] INFO Starting clean up.
2023-09-07T23:44:27Z app[xxx] nrt [info] WARN hallpass exited, pid: 256, status: signal: 15 (SIGTERM)
2023-09-07T23:44:27Z app[xxx] nrt [info]2023/09/07 23:44:27 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:28Z app[xxx] nrt [info][ 2.293042] reboot: Restarting system
2023-09-07T23:44:28Z runner[xxx] nrt [info]machine did not have a restart policy, defaulting to restart
2023-09-07T23:44:31Z app[xxx] nrt [info][ 0.036444] PCI: Fatal: No config space access function found
2023-09-07T23:44:31Z app[xxx] nrt [info] INFO Starting init (commit: 5293a085)...
2023-09-07T23:44:31Z app[xxx] nrt [info] INFO starting statics vsock server
2023-09-07T23:44:31Z app[xxx] nrt [info] INFO Preparing to run: `/rails/bin/docker-entrypoint supercronic /rails/crontab` as rails
2023-09-07T23:44:31Z app[xxx] nrt [info] INFO [fly api proxy] listening at /.fly/api
2023-09-07T23:44:31Z app[xxx] nrt [info]2023/09/07 23:44:31 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:31Z app[xxx] nrt [info]/rails/bin/docker-entrypoint: line 5: exec: supercronic: not found
2023-09-07T23:44:32Z app[xxx] nrt [info] INFO Main child exited normally with code: 127
2023-09-07T23:44:32Z app[xxx] nrt [info] INFO Starting clean up.
2023-09-07T23:44:32Z app[xxx] nrt [info] WARN hallpass exited, pid: 256, status: signal: 15 (SIGTERM)
2023-09-07T23:44:32Z app[xxx] nrt [info]2023/09/07 23:44:32 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:33Z app[xxx] nrt [info][ 2.285410] reboot: Restarting system
2023-09-07T23:44:33Z runner[xxx] nrt [info]machine did not have a restart policy, defaulting to restart
2023-09-07T23:44:38Z app[xxx] nrt [info][ 0.036888] PCI: Fatal: No config space access function found
2023-09-07T23:44:38Z app[xxx] nrt [info] INFO Starting init (commit: 5293a085)...
2023-09-07T23:44:38Z app[xxx] nrt [info] INFO starting statics vsock server
2023-09-07T23:44:38Z app[xxx] nrt [info] INFO Preparing to run: `/rails/bin/docker-entrypoint supercronic /rails/crontab` as rails
2023-09-07T23:44:38Z app[xxx] nrt [info] INFO [fly api proxy] listening at /.fly/api
2023-09-07T23:44:38Z app[xxx] nrt [info]2023/09/07 23:44:38 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:38Z app[xxx] nrt [info]/rails/bin/docker-entrypoint: line 5: exec: supercronic: not found
2023-09-07T23:44:39Z app[xxx] nrt [info] INFO Main child exited normally with code: 127
2023-09-07T23:44:39Z app[xxx] nrt [info] INFO Starting clean up.
2023-09-07T23:44:39Z app[xxx] nrt [info] WARN hallpass exited, pid: 256, status: signal: 15 (SIGTERM)
2023-09-07T23:44:39Z app[xxx] nrt [info]2023/09/07 23:44:39 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:40Z app[xxx] nrt [info][ 2.297464] reboot: Restarting system
2023-09-07T23:44:41Z runner[xxx] nrt [info]machine did not have a restart policy, defaulting to restart
2023-09-07T23:44:52Z app[xxx] nrt [info][ 0.035700] PCI: Fatal: No config space access function found
2023-09-07T23:44:52Z app[xxx] nrt [info] INFO Starting init (commit: 5293a085)...
2023-09-07T23:44:53Z app[xxx] nrt [info] INFO starting statics vsock server
2023-09-07T23:44:53Z app[xxx] nrt [info] INFO Preparing to run: `/rails/bin/docker-entrypoint supercronic /rails/crontab` as rails
2023-09-07T23:44:53Z app[xxx] nrt [info] INFO [fly api proxy] listening at /.fly/api
2023-09-07T23:44:53Z app[xxx] nrt [info]2023/09/07 23:44:53 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:53Z app[xxx] nrt [info]/rails/bin/docker-entrypoint: line 5: exec: supercronic: not found
2023-09-07T23:44:54Z app[xxx] nrt [info] INFO Main child exited normally with code: 127
2023-09-07T23:44:54Z app[xxx] nrt [info] INFO Starting clean up.
2023-09-07T23:44:54Z app[xxx] nrt [info] WARN hallpass exited, pid: 256, status: signal: 15 (SIGTERM)
2023-09-07T23:44:54Z app[xxx] nrt [info]2023/09/07 23:44:54 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:44:55Z app[xxx] nrt [info][ 2.286372] reboot: Restarting system
2023-09-07T23:44:55Z runner[xxx] nrt [info]machine did not have a restart policy, defaulting to restart
2023-09-07T23:45:11Z app[xxx] nrt [info][ 0.036692] PCI: Fatal: No config space access function found
2023-09-07T23:45:11Z app[xxx] nrt [info] INFO Starting init (commit: 5293a085)...
2023-09-07T23:45:11Z app[xxx] nrt [info] INFO starting statics vsock server
2023-09-07T23:45:11Z app[xxx] nrt [info] INFO Preparing to run: `/rails/bin/docker-entrypoint supercronic /rails/crontab` as rails
2023-09-07T23:45:11Z app[xxx] nrt [info] INFO [fly api proxy] listening at /.fly/api
2023-09-07T23:45:11Z app[xxx] nrt [info]2023/09/07 23:45:11 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:45:11Z app[xxx] nrt [info]/rails/bin/docker-entrypoint: line 5: exec: supercronic: not found
2023-09-07T23:45:12Z app[xxx] nrt [info] INFO Main child exited normally with code: 127
2023-09-07T23:45:12Z app[xxx] nrt [info] INFO Starting clean up.
2023-09-07T23:45:12Z app[xxx] nrt [info] WARN hallpass exited, pid: 256, status: signal: 15 (SIGTERM)
2023-09-07T23:45:12Z app[xxx] nrt [info]2023/09/07 23:45:12 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:45:13Z app[xxx] nrt [info][ 2.292211] reboot: Restarting system
2023-09-07T23:45:13Z runner[xxx] nrt [info]machine did not have a restart policy, defaulting to restart
2023-09-07T23:45:53Z app[xxx] nrt [info][ 0.035741] PCI: Fatal: No config space access function found
2023-09-07T23:45:53Z app[xxx] nrt [info] INFO Starting init (commit: 5293a085)...
2023-09-07T23:45:53Z app[xxx] nrt [info] INFO starting statics vsock server
2023-09-07T23:45:53Z app[xxx] nrt [info] INFO Preparing to run: `/rails/bin/docker-entrypoint supercronic /rails/crontab` as rails
2023-09-07T23:45:53Z app[xxx] nrt [info] INFO [fly api proxy] listening at /.fly/api
2023-09-07T23:45:53Z app[xxx] nrt [info]2023/09/07 23:45:53 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:45:53Z app[xxx] nrt [info]/rails/bin/docker-entrypoint: line 5: exec: supercronic: not found
2023-09-07T23:45:54Z app[xxx] nrt [info] INFO Main child exited normally with code: 127
2023-09-07T23:45:54Z app[xxx] nrt [info] INFO Starting clean up.
2023-09-07T23:45:54Z app[xxx] nrt [info] WARN hallpass exited, pid: 256, status: signal: 15 (SIGTERM)
2023-09-07T23:45:54Z app[xxx] nrt [info]2023/09/07 23:45:54 listening on [fdaa:2:5a3e:a7b:fc:a19d:2e0b:2]:22 (DNS: [fdaa::3]:53)
2023-09-07T23:45:55Z app[xxx] nrt [info][ 2.286436] reboot: Restarting system
2023-09-07T23:45:56Z runner[xxx] nrt [info]machine has reached its max restart count (10)