Issues with Lets Encrypt and Deploy

I initially had ssl enabled set to false in the production “wordpress_sites.yml” file and deployed my site to an Azure Ubuntu VM just fine. However, when I change ssl enabled to true (with letsencrypt as the provider), update my git repo and deploy it, I just end up with a failed to connect error. It is redirecting to https, but not loading the site. I do have port 443 open with the protocol as TCP.

I’m not seeing any mention in the terminal logs about lets encrypt either. It doesn’t seem like it was setup.

I’m deploying with:
ansible-playbook deploy.yml -e “ env=production”

For anyone running into this issue, I had to re-provision my local vm using

$ vagrant provision


Then I had to re-provision the remote server using

$ ansible-playbook server.yml -e env=<environment>


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