I’ll show how to obtain a certificate with letsencrypt and how to add it Postfix and Dovecot. As a side effect it fixes mail-sending in Wordpress.

Dammit. An apt-get upgrade broke mail sending from Wordpress. The setup is similar to the one covered in Tutorial: Use personal gmail with @yourdomain.com, but basically, it’s like this: mails are sent using a local Postfix instance and Dovecot is used for SMTP authentication.

Investigating the mail log shed a little light on the cause:

Apr  4 14:51:32 garagehaven postfix/smtpd[6856]: SSL_accept error from localhost[]: 0
Apr  4 14:51:32 garagehaven postfix/smtpd[6856]: warning: TLS library problem: error:14094418:SSL routines:SSL3_READ_BYTES:tlsv1 alert unknown ca:s3_pkt.c:1262:SSL alert number 48:

Clearly the problem was related to SSL. To dig further, I created the following Wordpress mail sending test.


  require( dirname( __FILE__ ) . '/wp-blog-header.php' );

  $message = 'test'; 
  wp_mail( 'jakob@example.com', 'subject', 'message');

And ran it with hhvm.

$ hhvm mail-test.php
Warning: SSL operation failed with code 1. OpenSSL Error messages:
error:14090086:SSL routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify failed in /srv/www/garagehaven/wp-includes/class-smtp.php on line 344

The certificate can’t be verified, and some PHP code chokes. This is no surprise, because, shame on me, I used a self-signed certificate. Luckily, with letsencrypt.org we can now obtain a certificate. This is how to install it.

Obtaining a certificate with letsencrypt

Check out the letsencrypt tool from github

sudo git clone https://github.com/letsencrypt/letsencrypt /opt/letsencrypt

Create certificate

/opt/letsencrypt/letsencrypt-auto certonly -a webroot --webroot-path=/srv/www/garagehaven -d garagehaven.dk

Wait. Was that it? How did letsencrypt know that we are indeed on that domain. Easy, it added a file to the webroot. Fetched it and voila – a once so painful process eliminated.

Add certificate to Postfix and Dovecot

Update Postfix

postconf 'smtpd_tls_key_file = /etc/letsencrypt/live/garagehaven.dk/privkey.pem'  
postconf 'smtpd_tls_cert_file = /etc/letsencrypt/live/garagehaven.dk/cert.pem'  
postconf 'smtpd_tls_CAfile = /etc/letsencrypt/live/garagehaven.dk/chain.pem'  

Update Dovecot


ssl_cert = </etc/letsencrypt/live/garagehaven.dk/cert.pem  
ssl_key = </etc/letsencrypt/live/garagehaven.dk/privkey.pem  

And reload the services

$ postfix reload
$ dovecot reload

And Wordpress can now send mails again.

Update certificate automatically with CRON

The certificate times out after 90 days. Thus, it’s essential to automate updates. But, that’s easy with cron and letsencrypt.

$ crontab -e
1 3 * * 1 /opt/letsencrypt/letsencrypt-auto renew >> /var/log/le-renew.log  
5 3 * * 1 /etc/init.d/postfix reload  
10 3 * * 1 /usr/sbin/dovecot reload  

Every monday at 3am, certificates are checked and renewed if stale.


No fiddling with openssl. No pasting signatures into a CA. No frustration. Just one simple command to rule them all. Letsencrypt people – you rock!