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Any suggestions for good guides for setting up LetsEncrypt with something like, say, a DigitalOcean droplet with a default Wordpress install?

certbot[1] is a tool for automating the Lets Encrypt process on something like a DO droplet. there's some info about SSL in the wordpress docs[2]

1. https://certbot.eff.org/

2. https://make.wordpress.org/support/user-manual/web-publishin...

If you're using apache, mod_md will automatically setup LE for you: https://httpd.apache.org/docs/trunk/mod/mod_md.html

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