I struggled very much with the almost identical problem of installing SSL Certs in a Heroku application with DNSimple and RapidSSL and want to post my solution here if someone with a similar problem encounters this answer.
I followed the directions throughout SO and Heroku dev center to install certificates through DNSimple and RapidSSL, but every time I tried to add certificates using the command:
$ heroku certs:add server.crt bundle.pem server.key
no matter what i did, i got this error:
$ Adding SSL Endpoint to mysite... failed ! Key could not be read since it protected by a passphrase. ! Read instructions on how to remove the passphrase on: ! http:
I knew that the key did not have a key phrase (because I went through this process several times), but he still did not want to add them. I did two things that eventually made her work, although I'm not sure which one was the key.
First, Iβve definitely downloaded the proper PEM file into the Apache, Plesk and CPA fields from the RapidSSL email link to the middle tier certificates.
Secondly, to verify the installation of the Herobu toolbelt tool, follow these steps: https://devcenter.heroku.com/articles/heroku-command#installing-the-heroku-cli
It turns out that I was still using the gem, and I had to remove it until I got to the hero-tool, after which I again tried to add certificates and voila.
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