Your VM will boot and a large amount of scrolling text will be on the screen.  This is normal.  Eventually, the scrolling will stop, and you can type in your username and password.

If you are comfortable using SSH, you can use SSH to connect to your machine at this time.  From Terminal on macOS, you can type ssh youruser@ipaddress to login.  For my example setup, I would type ssh bradkovach@  A message about the authenticity of the host may appear.  It is safe to accept this host.

8. Install the VPN service

  1. Once you are logged in to your new Ubuntu Server installation, you should see a prompt, yourusername@yourbusinessname:~$ .  For my example installation for the United Way, the prompt reads bkovach@uwacwy:~$ .
  2. From here, you can issue commands to the system.  We will issue a few commands that will set up our VPN server.

First, update and install all software updates.  Type the following commands. When you press enter, it may ask for your password.

sudo apt update <enter>
sudo apt upgrade -y <enter>

Once the software updates are finished installing, you will be returned to your command prompt.  At this point, reboot the virtual machine.

sudo reboot <enter>

Login using your username and password again.

You are now ready to install the software for the VPN server. Issue the following command to download and start the installer.

curl -L | bash <enter>

The installer will show a warning.  This is okay.  Select <yes> and press [enter] to continue.

PiVPN: A warning about an Untested OS will appear. Highlight <Yes> and press [Enter] to continue.

Some text will scroll, and the installer will prompt [sudo] password for user: .  Type your user password here and press [enter].

Enter your password and press [enter]

A series of prompts will appear about static IP addresses.  We already assigned a static IP address earlier, so we can safely ignore these messages.

  1. PiVPN Automated Installer screen: select <Ok> and press [enter]
  2. IP Information screen: select <Ok> and press [enter]
  3. Local Users screen: select <Ok> and press [enter].
  4. Choose A User screen: use the arrow keys to select your user and press space to select it if it isn’t already selected.  Select <Ok> and press [enter]
  5. Installation mode screen: Select OpenVPN and press space to select it. Select <Ok> and press [enter]
  6. Installing packages screen: wait for the installation to complete
  7. Protocol screen: leave UDP selected, select <Ok> and press [enter]
  8. Default openvpn Port screen: leave the port set to 1194, unless you know you need to use a different port. Select <Ok> and press [enter].
  9. Confirm Custom Port Number screen: Verify the settings, and select <Yes> to accept the port configuration.
  10. Select the DNS provider screen: pick a DNS provider option.  For most cases, Quad9 or OpenDNS work well.  If you need a different DNS setup for any reason, specify that setting here.  When you’re done, select <Ok> and press [enter]
  11. Custom Search Domain screen
    1. if you are using Omega Consulting dynamic DNS, select <Yes> and press [enter].
    2. For the search domain, type
    3. Select <Ok> and press [enter].
    4. Verify the custom search domain settings, select <Yes> and press [enter]
  12. Public IP or DNS screen: it is recommended that you set up your VPN server to use a DNS entry, which is much easier to remember than an IP address.  You can use Omega Consulting’s dynamic dns service to get a free DNS entry. Select “DNS Entry”, press [space] to select, then highlight <Ok> and press [enter]
    1. PiVPN Setup screen: For the public DNS name of this server, type your computer name specified earlier followed by For the United Way example, this is
  13. Installation mode screen: Use the new 2.4 settings.  Select <Yes> and press [enter].
  14. ECDSA certificate size screen: Select 256, select <Ok> and press [enter].
  15. Server Information screen: press <Ok>
  16. Unattended Upgrades screen
    1. Select <Ok> and press [enter]
    2. Select <Yes> and press [enter]
  17. Reboot screen: it is recommended that you reboot the machine at this time.  Select <Yes> and press [enter]
  18. Rebooting screen: select <Ok> and press [enter].
  19. Wait for the machine to reboot, login and proceed to the user setup process.

NEXT: Add VPN Users