tls

Fixing Safari's 'can't establish a secure connection' when updating a self-signed certificate

I do a lot of local development, and since almost everything web-related is supposed to use SSL these days, and since I like to make local match production as closely as possible, I generate a lot of self-signed certificates using OpenSSL (usually using Ansible's openssl_* modules).

This presents a problem, though, since I use Safari. Every time I rebuild an environment using my automation, and generate a new certificate for a domain that's protected with HSTS, I end up getting this fun error page:

Safari Can't Open the Page - Safari can't open the page because Safari can't establish a secure connection to the server servername.

Safari Can't Open the Page – Safari can't open the page because Safari can't establish a secure connection to the server 'servername'.

Self-signed certificates via Ansible for local testing with Nginx

Most of my servers are using TLS certificates to encrypt all traffic over HTTPS. Since Let's Encrypt (and certbot) have taken the world of hosting HTTPS sites by storm (free is awesome!), I've been trying to make sure all my servers use the best settings possible to ensure private connections stay private. This often means setting up things like HSTS, which can make local / non-production test environments harder to manage.

Consider the following:

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