Let's Encrypt with FreeNAS 11.1 and later

With 25.04 I’d probably use a LXC instance instead, but that’s neither here nor there. Is the script executable? What are its permissions?

This is what I get with the stat command.

File: deploy_truenas.py
Size: 10292 Blocks: 17 IO Block: 10752 regular file
Device: 0,169 Inode: 23584 Links: 1
Access: (0644/-rw-r–r–) Uid: ( 0/ root) Gid: ( 0/ root)
Access: 2025-05-28 14:57:39.002131697 -0400
Modify: 2025-05-28 14:57:39.002131697 -0400
Change: 2025-05-28 14:57:39.002131697 -0400
Birth: 2025-05-28 14:57:39.002131697 -0400

There’s your problem. chmod +x deploy_truenas.py.

Thanks I changed the permission, but unfortunately another issue is popping up. If put in the following commands I get no such file or directory error.

acme.sh --install-cert -d thewall.duckdns.org --reloadcmd “~/deploy-freenas/deploy_truenas.py”

/root/.acme.sh/acme.sh: line 5992: /root/deploy-freenas/deploy_truenas.py: No such file or directory

acme.sh --install-cert -d thewall.duckdns.org --reloadcmd “/deploy-freenas/deploy_truenas.py”

/usr/bin/env: ‘python3’: No such file or directory

You’re missing dependencies in your jail. Consult the README for what you need: