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Troubleshooting
If you run into an error, check the following list of errors and remedies first:
This probably means that Let's Encrypt cannot get to the validation file. The client is creating a folder called .well-known in the directory specified by public with a series of subdirectories and a file. The file should be accessible on each domain you are trying to create (redirects appear to be allowed). For example, if the file on disk is /home/myuser/webapps/myapp/htdocs/.well-known/1234/1234, and the domain you are verifying is test.example.com, then http://test.example.com/.well-known/1234/1234 should be accessible from the internet. In this example, you would have added public = "/home/myuser/webapps/myapp/htdocs/" to the config.
This probably means that for some reason Ruby is using an odd certificate authority file. You can usually override this by running SSL_CERT_FILE=/etc/ssl/certs/ca-bundle.crt letsencrypt_webfaction run.
If this still doesn't work, try running:
cd ~
wget http://curl.haxx.se/ca/cacert.pem
SSL_CERT_FILE=~/cacert.pem letsencrypt_webfaction runjson-jwt-1.5.2/lib/json/jwk/jwkizable.rb:69:in '<top (required)>': uninitialized constant OpenSSL::PKey::EC (NameError)
You are probably using a CentOS 5 box, which has an older version of OpenSSL and doesn't support the Elliptic Curve algorithm that json-jwt depends on.
You can try to compile your own OpenSSL and then use it as the basis for setting up RBenv and compiling your own Ruby.
Here are the instructions for setting this up on an older WebFaction box.
If you see something like:
sendmail: authentication failed (method CRAM-MD5)
sendmail: server message: 535 5.7.0 Error: authentication failed: authentication failure
sendmail: could not send mail (account default from dummy)
sendmail: authentication failed (method CRAM-MD5)
sendmail: server message: 535 5.7.0 Error: authentication failed: authentication failure
sendmail: could not send mail (account default from dummy)
Run echo "Subject: Test Email" | sendmail youremail@example.com on your server, substituting your email address for the example. If this doesn't work, open a ticket with Webfaction support to get this much working, then try Letsencrypt Webfaction again.