Darren Mothersele

Software Developer

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How to Be a Cloud Survivalist (part 3)

Dec 16, 2013


This is the third post in a series where I document the process of implementing your own suite of cloud services. I covered the requirements in the previous post, and in this instalment I take a deeper look at what it takes to run your own email service.

Email server overview

Setting up an email server has a reputation for being incredibly complicated, and needing a lot of work to keep safe and secure. The reasons for this are two fold: There are a lot of bits of technology involved in sending and delivering email, and secondly, there are a lot of criminals out there looking for vulnerable servers to exploit in order to send spam.

The main components of a mail system are

You will also need:

While researching the various options, and looking at how to configure them to work together I came across iRedMail, a fully-fledged email solution. It doesn’t re-implement any existing technology and instead builds on top of popular and robust open-source projects, it uses your OS package manager to install the requirements, and then configures each bit to work together. It can be configured to use LDAP or MySQL as a back-end for storing user accounts.

Getting started

I’m going to demonstrate the process of setting up an email server using a VPS server at Digital Ocean, and I’m going to use Ubuntu 12.04 because that is the OS I’m most familiar with. The process should be pretty similar for your own choice of host and OS.


In How to Be a Cloud Survivalist (part 1), I mentioned that when you run your own mail server there is a higher chance that receiving servers will flag your email as spam. There are various mechanisms that have been developed for identifying bogus email, and we have to configure various things to get around this and prevent our email being flagged as spam.

The first of these measures is to ensure you have a valid PTR record setup for your server in the DNS. A PTR record does the opposite of what an A record does. With a A record you are telling the DNS system what IP address to go to for a given domain name. A PTR record registers a domain name for a given IP address so it is also called a reverse DNS record.

A PTR record is used to check that the sending server name is actually associated with the IP address from which the connection was initiated. So, in email sending, the receiving server can find the server name using a reverse DNS lookup, then check this matches against the mail server settings for the email domain of the sender.

If you control the authoritative DNS for the IP address of the server you are using then you will need to configure the reverse DNS records yourself, otherwise you’ll have to contact your ISP or hosting company. I’m using Digital Ocean, and they automatically configure the PTR record to match the hostname you use when you provision your server.

STEP 1: Provision server

As discussed above, in order to get the correct PTR record for the server, enter a name for the server that matches the name you will be using when you assign the server as a mail server in your email domain’s DNS records.

You can’t actually create the DNS settings for the domain until you’ve provisioned the server and know it’s IP address. I’ll assume you’re going to be using example.com as your main domain, and so we’ll use mx.example.com for the server name.

Screenshot of provisioning server

I’ve selected a 1GB instance as the iRedMail requirements suggest this much memory if you are going to enable spam filtering of incoming email.

STEP 2: Register domain, DNS settings

After you have registered your name (I’ll stick to convention and use example.com in the examples), you should set up some DNS settings. The process for doing this will depend on where where you registered your domain.

I don’t have any recommendations for domain registrars. This time I used 123-reg, but I’m not going to recommend them because they have told me they are NOT implementing 2-factor authentication and they have no plans to do so.

I’m using a separate domain for setting up email services, so I’ve registered a cheap £9 SSL cert for that domain just to get rid of browser security warnings. This only certifies one domain so be sure to use the domain name you want to be using for your mail server settings, and not the same as your website (if you have one) as you don’t want to tie your website to the same domain as your email as you probably want to run them on separate servers.

So, if you’re using mail.example.com or example.com (depending on your SSL cert) create A records that point at the IP address of the server you configured in the last step.

Also, create an A record for mx.example.com and point this at the IP address of the server. Then create an MX record for your domain and point it at mx.example.com.

You should check the certification process for registering your SSL certificate, as the site I used required sending an email to the domain as part of the ownership verification process. Obviously, you will need to have email setup in order to do this so you may have to come back to SSL setup once you have email up and running with a self-signed certificate.

An SPF record is another measure in the battle against spam. This is a record in the DNS for a domain that specifies which hosts are allowed to send email on behalf of this domain. You will need to create this (as a TXT record) in the DNS for every domain name you will be hosting email for. The SPF record should look like this, but with x.x.x.x replaced with your server IP address:

"v=spf1 ip4:x.x.x.x -all"

There are also DNS records that need to be created for DKIM but I’ll explain what this is all about in a bit, as you need to configure the mail server first.

STEP 3: Install iRedMail

I selected to add my SSH key to the server when I provisioned it, so login is straightforward, and doesn’t need a password. First thing I do is add a Linux account for myself, so I don’t have to login as the root user, give myself sudo privileges, disable root and password logins via SSH, and update all packages with ap-get update ; apt-get upgrade.

Now on to configure iRedMail. You’ll need sudo access for this. So, as the root user, download and extract the iRedMail package:

cd /root
wget https://bitbucket.org/zhb/iredmail/downloads/iRedMail-0.8.6.tar.bz2
tar xjf iRedMail-0.8.6.tar.bz2

Then change into the iRedMail directory and execute the installer:

cd iRedMail-0.8.6/
bash iRedMail.sh

You should then be presented with this welcome screen. Please note that I took these screenshots last week and so they are of v0.8.5.

iRedMail welcome screen

Once you go past the welcome screen you will see a series of screens that prompt you for various bits of information. First select the location on the file system to store the mail boxes. I see no reason not to go with the default:

Select a back-end to use for storage of user accounts. I prefer LDAP for this as I’ll be using it to integrate with some of the other components of my cloud services in addition to email.

When you create your LDAP suffix, work from just the domain name. So, even though the server name is mx.example.com, you should just use example.com to calculate your LDAP suffix. In fact, I’m going to add extra domains later and I’m not really going to use this domain name for user accounts.

Make sure you generate a secure (truly random) password for the LDAP root:

Enter the domain name for this server. This is going to be the domain name you use in email settings later. It should match the domain name that you have (or will) generate the SSL certificate for:

There are some optional extras you can install. I’m going to install all of them except the phpMyAdmin and phpLDAPadmin as I don’t want to maintain these two bits of software. phpMyAdmin in the past has been a source of security vulnerabilities and I’m not going to use it anyway, so no point having it installed.

Once you’ve provided values for all the options the configuration will continue automatically and you will see progress reported. You will see a couple of questions along the way that you can answer y/n to.

iRedMail has now finished installing and configuring the packages, during this process it created some firewall rules. I’m just going check what they are using sudo iptables -L, once I’ve confirmed I’m happy with them I reboot the server.

Once the server has finished rebooting and it back online, I browse to my domain in a web browser and I see this:

Configure iRedMail to use custom SSL certificate

When you install iRedMail it creates it’s own self-signed certificate for SSL communication. In order to get rid of browser warnings I’m going to install my own certificate.

After verifying ownership of the domain name I was given two files. The first is my actual certificate, the second is the chain of certificates that verify my certificate. I also have the private key I used when creating the certificate signing request. I need all three of these files, so I upload them to the server and move them to the appropriate places. Put the private key in /etc/ssl/private, and the other two files in /etc/ssl/certs so you have something that looks like this:


Now in your Apache configuration (/etc/apache2/sites-enabled/default-ssl) find the appropriate place for SSL keys, remove the references to self-signed certificates, and enter location of your SSL certs and keys:

SSLCertificateFile /etc/ssl/certs/example.com.crt
SSLCertificateKeyFile /etc/ssl/private/example.com.key
SSLCertificateChainFile /etc/ssl/certs/example.com.ca.crt

Once you restart Apache that should remove the browser warnings. We also need to update the certificates in use by dovecot and postfix to prevent SSL error messages when sending and receiving email via other apps.

For dovecot and postfix we don’t use separate chain and cert files, so we need to concatenate them into a single file (eg /etc/ssl/certs/example.chain.cert), in this order:

  1. Your public SSL certificate
  2. The provided CA certificate
  3. Any other root CA certificate for signer of your SSL

For incoming email (IMAP/POP) update the dovecot configuration in /etc/dovecot/dovecot.conf and update the following to point at your cert and key files:

ssl_key_file = /etc/ssl/private/example.com.key
ssl_cert_file = /etc/ssl/certs/example.chain.key

For outgoing email (via SMTP), change below lines in /etc/postfix/main.cf:

smtpd_tls_key_file = /etc/ssl/private/example.com.key
ismtpd_tls_cert_file = /etc/ssl/certs/example.chain.key

Now restart the services so the changes take effect.

sudo service apache2 restart
sudo service postfix restart
sudo service dovecot restart

You should now be able to connect to iRedAdmin and Roundcube via the web interface without getting SSL error messages.

DomainKeys Identified Mail

One more bit of configuration that needs setting up is DKIM. This is another change to make to the DNS records that helps ensure deliverability of emails and that you wont get flagged as a spammer or unknown mail server.

DKIM was installed and configured by iRedMail. Logged in as root, run the following command to see a list of the keys.

amavisd-new showkeys

You will see something like the following output:

; key#1, domain example.com, /var/lib/dkim/example.com.pem
dkim._domainkey.example.com. 3600 TXT (

In the DNS settings for your domain, create a new TXT record for dkim._domainkey and enter the whole string that is shown between () in the output of the showkeys command. Once you have created the DNS record, you will need to wait a while for the change to propagate, then you can test your keys are working correctly with the testkeys command:

# amavisd-new testkeys
TESTING#1: dkim._domainkey.example.com    => pass

Once you have verified that the key is working here, you can use a verification service to test deliverability of your email. I found the port25 service useful, all you have to do is send an email to [email protected] and you will get a response with lots of useful information, summarised like this:

Configure mail client

You should now be ready to start using your email server. When you setup your account you will probably have to select “Manual configuration”, or if a list of standard email providers is listed then select “Other”.

The server address is your domain (example.com), you should select IMAP for incoming mail. Note that the mail server is example.com and not imap.example.com which some software defaults to. Make sure you use the full email address as the account name, else you may be prompted for a “prefix”. The outgoing email server is SMTP and again is on example.com and not smtp.example.com as some apps will default to.

Adding an extra domain to iRedMail

I wanted to add accounts for friends and have email hosted for some other domain names. Here’s how to add an extra domain name to iRedMail.

The first, simple, step is to add the domain to iRedAdmin. I wont explain this as it’s very straightforward. Once you’ve done that you need to add the domain to the DKIM configuration.

Login as root to the server, change into the folder where DKIM keys are stored and generate a new key for the domain:

cd /var/lib/dkim
amavisd-new genrsa test.com.pem
chmod 0644 test.com.pem

Now edit the confuration file at /etc/amavis/conf.d/50-user to include the new key. Find the section in the configuration file where keys are declared and add:

dkim_key("test.com", "dkim", "/var/lib/dkim/test.com.pem");

Then find where the local domains are defined (in the same config file) and add your new domain:

@local_domains_maps = ['mx.example.com', 'example.com', 'test.com'];

Restart amavis and show the new list of keys. You should see your new key listed. Copy the TXT record and add it to the DNS for the new domain:

/etc/init.d/amavis restart
amavisd-new showkeys

Also remember to add the SPF record to the new domain, and set the MX records so they point at mx.example.com.

You may want to send an email to [email protected] from the new domain just to check everything is working correctly.

Check logs

Once you start using your new email server you will want to check the logs now and again to check everything is running OK. I looked in /var/log/mail.log and noticed a couple of real emails being rejected. To be fair it was actually due to misconfiguration of the sending mail server, but I still wanted these emails to get through.

I had comment out the following line from /etc/postfix/helo_access.pcre to allow these messages through:

/\.local$/                  REJECT Go away, bad guy (.local).


Now I’ve got email working, and thanks to IMAP, I have my email accessible across all my devices. In the next post in this series I’m going to take a slight detour while I look more at what is possible now I have a working LDAP server for my domain. Then I’m going to quickly move on to implementing other cloud services, in particular the synchronisation of other data across my devices, like calendars and contacts.