I'm looking for information on how to configure an HTTP load balancer or proxy server (squid, nginx, HAProxy, etc.) to handle the SSL for my domain as an alternative to adding Heroku's SSL Endpoint add-on for $20/month.
The load balancer or proxy server would terminate the SSL connection and the last leg to the heroku server would be over http.
SSL is now included on all paid dynos. Thus, you pay only the certificate price.
https://blog.heroku.com/ssl-is-now-included-on-all-paid-dynos
A new add-on was added a few short months ago called Expedited SSL. This add-on provides you with both the registration of an SSL certificate along with the endpoint for serving it, whereas SSL Endpoint is only the endpoint used to serve the SSL certificate you've already purchased from an SSL provider.
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