This guide covers how to create the box and add it to your list of boxes, for use in specifying within a Vagrantfile. It doesn’t cover Vagrant fundementals, so I assume that you’ll have some basic knowledge in how it works before embarking on this magical quest.

1. Open VMware Fusion

2. Select “Install from disc or image” and click “Continue”

3. Locate the ISO for the distribution you want to install, then select “Open”, and click “Continue”.

4. Unselect the checkbox for “Use Easy Install”

5. Choose “Customize Settings”, and enter a name for the VMware file (name/OSarch, i.e. wegotoeleven/trusty64) and select “Save"

6. Customise the VM’s settings

   1. Turn on Shared Folders
   2. Set memory to desired size, at least 1024MB
   3. Change the Networking to “Share with my Mac” (aka NAT)
   4. Change the disk size to 40 GB and deselect “Split into 2GB files”
   5. Turn off the sound card
   6. Expand “Advanced USB options” and select “Remove USB Controller”
   7. Untick “Share Mac printers with Linux”

7. Boot the VM, install the Guest OS and customise the following settings when prompted:

8. Host Name: Same as the second part of the name of the VMware file (i.e. trusty64)

9. Full Name: vagrant

10. User: vagrant

11. Password: vagrant

12. Once setup and at the command prompt, login and change the Root Password. When asked, set to vagrant

    $ sudo passwd root
    

13. Update the OS because updates

    $ sudo apt update && sudo apt upgrade -y
    

14. Update the Sudoers file with the following to allow the vagrant user sudo rights without having to authenticate with a password

    #Defaults !visiblepw
    Defaults env_keep="SSH_AUTH_SOCK"
    

15. Test. Is the following command outputs the current directory instead of an error, all is good

    $ sudo pwd
    

16. Restart VM

    $ sudo shutdown -r now
    

17. Make ssh folder

    $ mkdir ~/.ssh
    

18. Set permissions

    $ chmod 700 ~/.ssh
    

19. Download Vagrant authorised keys

    $ wget --no-check-certificate https://raw.github.com/mitchellh/vagrant/master/keys/vagrant.pub -O ~/.ssh/authorized_keys
    

20. Set permissions on authorised keys file

    $ chmod 600 ~/.ssh/authorized_keys && chown -R vagrant ~/.ssh
    

21. Install OpenSSH

    $ sudo apt install openssh-server -y
    

22. Edit the SSH config file

    $ sudo nano /etc/ssh/sshd_config
    

23. Restart SSH service

    $ sudo service ssh restart
    

24. Install VMware Tools. Begin by mounting the VMware Tools by selecting Virtual Machines > Install VMware Tools from the menu bar menu

    $ sudo mkdir -p /mnt/cdrom
    $ sudo mount /dev/cdrom /mnt/cdrom
    $ tar xzvf /mnt/cdrom/VMwareTools-9.2.2-893683.tar.gz -C /tmp
    $ cd /tmp/vmware-tools-distrib/
    $ sudo ./vmware-install.pl\
    

25. Wipe the free space on the VM to stop fragmentation

    $ sudo dd if=/dev/zero of=/EMPTY bs=1M
    $ sudo rm -f /EMPTY
    

26. Shutdown the VM

    $ sudo shutdown -h now
    

27. Navigate to the location of your vmwarevm. By default this location is ~/Virtual Machines/.

    $ cd ~/Virtual Machines/wegotoeleven:xenial64.vmwarevm
    

    Note: Any forward slashes (/) will be translated into colons if the name of the VMware file contains a forward slash

28. Create a file named metadata.json and enter the following contents:

    {
      "provider": "vmware_fusion"
    }
    

29. Create a file named Vagrantfile and enter the following contents.

    # -*- mode: ruby -*-
    # vi: set ft=ruby
    
    Vagrant.configure("2") do |config|
      config.vm.provider :vmware_fusion do |v, override|
        v.gui = false
      end
    end
    

30. We next want to optimize the box to reduce it’s size:

    $ /Applications/VMware\ Fusion.app/Contents/Library/vmware-vdiskmanager -d Virtual\ Disk.vmdk
    $ /Applications/VMware\ Fusion.app/Contents/Library/vmware-vdiskmanager -k Virtual\ Disk.vmdk
    

31. Finally compress the box:

    $ tar cvzf package.box ./
    

32. Add the box to Vagrant

    $ vagrant box add wegotoeleven/xenial64 package.box
    

I couldn’t have done this without the following blog posts:

• creating-a-custom-box-from-scratch
• building-a-vagrant-box

And yeah. I know I said 30.

For context, this issue:

• Persisted between inventory updates
• Would only ever be present when connecting to WiFi (i.e. the issue abated when disabling WiFi and connecting to Ethernet)
• Would not be resolved by forgetting the SSID and/or deleting and re-adding the network interface
• Would not be affected by renewing the DHCP lease.

Doing some digging, the documentation for the “Reported IP Address” field in Jamf Pro notes that:

The reported IP address is collected by the jamf binary during a check-in and can be received by executing the following command:

ifconfig

While this is technically correct, the documentation doesn’t explicitly state where this information is collected from during an inventory; it’s actually parsed from a file on disk, /Library/Preferences/SystemConfiguration/preferences.plist. Searching though this file for the incorrect IP address highlighted that the user had many, many interfaces (typically caused when moving between desks that have hubs or monitors with build in Ethernet interfaces), and one of these used a Static IP address assignment:

IPV4 = {
	Addresses = (
		"10.14.28.1"
	);
	ConfigMethod = Manual;
	...
}

Finding and removing the static IP from the above interface immediately fixed the issue the next time that the Mac checked into Jamf Pro.

It does beg the question however, whether the “Reported IP Address” collection process in Jamf Pro could be improved to validate whether the interface is connected before logging it.