option 1) disable the ssl and raise all the errors so we can see them in the environment.rb or an initializer somewhere it can't be done in the config
ActionMailer::Base::raise_delivery_errors = true ActionMailer::Base::smtp_settings[:enable_starttls_auto] = false
option 2) rebuild your snake oil cert ..
before you do this check that its going to work
hostname openssl x509 -in /etc/ssl/certs/ssl-cert-snakeoil.pem -noout -text
if the hostnames already match then forget it.. otherwise execute these commands to fix it and check..
make-ssl-cert generate-default-snakeoil --force-overwrite openssl x509 -in /etc/ssl/certs/ssl-cert-snakeoil.pem -noout -text
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