My domain is properly setup with Let’s Encrypt SSL certificate

example.com + www.example.com

Now I want to add multi-language version of my websites on a subdomain like

en.example.com

If I create a new droplet with subdomain can I just run the same Let’s Encrypt auto installer and have SSL certificate for

en.example.com + www.en.example.com

Would this work without conflicts or would I need a wildcard-certificate?

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This will just work and you can use the autoinstall script to make this certificate. Let’s Encrypt actually doesn’t support Wildcards yet so its the only way:

Will Let’s Encrypt issue wildcard certificates?
We currently have no plans to do so, but it is a possibility in the future. Hopefully wildcards aren’t necessary for the vast majority of our potential subscribers because it should be easy to get and manage certificates for all subdomains.