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Scott Pinkelman

web development, data visualization, digital literacy

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Up and Running With Mail-in-a-Box


I’ve been trying to learn a lot more about data security and internet privacy, which lead to the Mailpile project. I’ve set that up with a Gmail account, but I wanted to try to try to “own my data” a little bit more, so I’ve decided to host my own email with Mail-in-Box. Running a mail server seems only slightly over my head, so it’s time to learn something new!

Mail-in-a-Box has a great setup guide and I’m not going to pretend to duplicate that. I want to write up my experience as additional reading for people who don’t have much experience with the linux command line, or are perhaps on the fence about trying somehting like this. Personally, I find reading multiple accounts of installing software helps me feel confident about starting a project, and prepared for when things go wrong. And lucky for you, gentle reader, several things went wrong in the process!


Mail-in-a-Box recommends a VPS with at least 1G of ram. Importantly, nothing else should be on your machine. I already have an account with Digital Ocean (ref link), so I decided to go with them. If you starting from scratch you can see Digital Ocean’s great documentation on getting started with Ubuntu 14.04.

The first thing I do is login to my Digital Ocean account panel and select a new droplet with Ubuntu 14.04 64 bit on it. It automatically adds my SSH keys, so I don’t need to be sent a root user password over email.

I look through the mail in a box documentation and read that the droplet must be the same name as the hostname. I go to the control panel and rename it, but there’s a message that reads:

This will update the displayed hostname of your droplet and the automatically generated PTR
record. It will not however modify your actual hostname inside of the system.

I consider going through with it, but I have a vague feeling that this is going to be an issue. More importantly, it’s so damned easy to destroy and create DO droplets, so I decide to start over. This time I name it

60 seconds later I’m back on track. I run through the initial server setup and disable root login (after all, what’s the point of hosting your own email if your root login gets compromised. Not so private, huh?)

I login with root and bam, I get this error:

 Someone could be eavesdropping on you right now (man-in-the-middle attack)! 
 It is also possible that a host key has just been changed. The fingerprint
 for the RSA key sent by the remote host is

A little research tells me that since I had already generated an RSA key for this server IP address in my first droplet, I needed to clear the last line of my known_hosts file in order to access the second droplet. I decided to clear it out manually. On my locallymachine I do:

cd ~/.ssh
nano know_hosts

and found my new droplet’s IP in the last line. I deleted the whole line CTRL+K, and closed and saved with CTRL+x.


I’m able to login, where I run Ubuntu updates. At this point, I read through the documentation again and see that I made an error when I registered my domain. When I bought the domain, I had automatically put the Digital Ocean nameservers, thinking I was cleverly saving myself some time. Not so. The Mail-in-a-Box needs to be set up with “glue” records pointing to the IP from the hostnames. The Mail-in-a-Box DNS instructions explain it more clearly than I will.

Installing Mail-in-a-Box

Finally, the big moment comes to install Mail-in-a-Box with the following command

curl -s | sudo bash

I follow the instructions and everything is smooth. Mail-in-a-Box recognizes my domain.

I hit a snag when I set up an admin password with spaces:

Okay. I'm about to set up for you. This account will also
have access to the box's control panel.

I enter my password, but it tells me:

Passwords cannot contain spaces.

FAILED: tools/ user make-admin
That's not a user (
alias added
added alias (=>
added alias (=>
added alias (=>

I run the setup script again, but the password part fails again. I end up finding the forums, where I see that I can access user controls from the command line with the following:

sudo tools/

which returns

  tools/ user  (lists users)
  tools/ user add [password]
  tools/ user password [password]
  tools/ user remove
  tools/ user make-admin
  tools/ user remove-admin
  tools/ user admins (lists admins)
  tools/ alias  (lists aliases)
  tools/ alias add
  tools/ alias add ','
  tools/ alias remove

With these commands, things are straightforward. I add the email address I want:

sudo tools/ user add

And wait for it to ask for a passowrd. I then reset the admin password.

tools/ user password [password here]

I end up not making my email an admin, and leaving what was set up initially (

That’s about it! All of the interface and instructions within Mail-in-a-Box are pretty clear. If you hit a snag that I managed to avoid, or want to learn more about the project, check out the Mail-in-a-Box forums.