- 1 Status of Support for Running Whonix ™ in VMware
- 2 Unofficial Supported VMware Products
- 3 About VMware
- 4 HowTo
- 5 Harden VMware products
- 6 VMware upstream bug reports
- 7 Troubleshooting
- 8 Footnotes
Status of Support for Running Whonix ™ in VMware
- Rarely (officially) tested
- It works, but highly experimental
- VMware is closed source, therefore security through obscurity.
- Recommended against
- Recommended to use a supported platform
Whonix ™ needs a contributor, maintainer, to support Whonix ™ in VMware!
What does "maintainer" mean in this context?
- Someone who runs those Test, LeakTests and tests from Protocol-Leak-Protection_and_Fingerprinting-Protection.
- Someone who otherwise looks around if everything is sane.
- User support, answering questions in the forums.
- Someone who creates, signs, uploads .ova images for VMware.
- Future development.
- Describes best security practices
Unofficial Supported VMware Products
VMware Workstation was tested. It is currently in a it works state, but rarely tested.
VMware ESX(i) (up to version 6.0) is tested and it works.
VMware Server or other products are untested, but most likely also in a it works state.
VMware Player is tested by an anonymous user in the old forum  and works as well. This is unconfirmed. Setting up the internal network can sometimes be tricky, this article contains instructions how to setup.
Maybe I am spoiled by Free Software (see  for definition). VMware is not very open, but in my opinion openness is important for security. I haven't found out how to submit a bug report. It looks like only buying customers may submit bug reports and there is only community support for products that are free in price. There is also no list with open bugs. Without a list of known bugs, I am unable to determine if VMware is suitable for Whonix ™, i.e. does not compromise the user's anonymity. Since bug reports remained entirely unanswered, it is also demotivating to investigate, contribute and submit further report bugs.
Do not forget to read the Documentation.
Newer third party video:
How to Install Whonix ™ 13 for Anonymous Web Browsing + Review on VMware Workstation [HD]
Importing the appliances:
- You can either import the Download version or manually build from source.
- Import Whonix-Gateway.ova and Whonix-Workstation.ova.
- Due to a VMware upstream bug, you may have to press retry when importing the .ova images (to relax the importing requirements).
Setting up the network:
- Connect the virtual network adapter to custom. This is important! No host-only, no NAT, no bridging! I used VMnet9 virtual network, as it wasn't used by anything else.
- Adjust the adapters with the following settings:
- Whonix-Gateway ™ set network adapter 2 to custom, /dev/vmnet8 (or on Windows probably: vmnet9).
- Whonix-Workstation ™ set network adapter 1 to custom, /dev/vmnet8 (or on Windows probably: vmnet9).
- Note: if vmnetX, such as for example vmnet8 is already used by the NAT adapter, do not re-use it for the custom adapter. In that case, use something else, such as vmnet9.
- Due to a VMware upstream bug, VM time is not set to UTC. Set VM time to UTC, otherwise Tor might not be able to connect.
Importing the .ova templates will simply not work. ESX(i) will not recognize the hardware family. However, there are workarounds, either extracting the .ova and editing the .ovf files or using VMware Workstation.
Importing virtual disk files
One way Whonix ™ can be made to run on ESXi is by extracting the .vmdk (VM virtual disk) files. An example can be found here.
Importing the appliances:
- Create two virtual machines in ESX(i) with default settings, do not create a virtual disk for them.
- Import both ova templates in VirtualBox, yes, VirtualBox.
- Once they are imported, grab the .vmdk disk files from their physical location on your disk (VirtualBox has extracted them from the .ova)
- Upload both disk files to the datastore that you are using in ESX(i)
- Attach the disk files to the appropriate virtual machines.
Set the networking:
- Make sure the Whonix-Gateway ™ has two network adapters configured as a virtual machine, the Whonix-Workstation ™ only one.
- Attach the first Whonix-Gateway ™ network adapter to your outside network vSwitch (this can be WAN, LAN, DMZ, ...)
- Attach the second Whonix-Gateway ™ network adapter to an isolated vSwitch. Preferably create a new vSwitch, which will be used only by Whonix-Gateway ™ and Whonix-Workstation ™. Attach no physical NICs to this vSwitch! Make sure you create a new vSwitch, not simply a new portgroup. Promiscuous mode within a vSwitch might screw you over.
- Attach the Whonix-Workstation ™ network adapter to the isolated vSwitch from previous step.
Once the machines boot, everything should come online nicely. Double check the vSwitch logic in your setup!
Unfinished: Alternate Workflow
If you prefer building from source, or the previous methods did not work, here is a method that was tested with 220.127.116.11.9, & ESXi 6.7.
Using a 64bit linux machine, build both gw & ws whonix flavors target raw
Example build phrase:
sudo ./build_whonix --flavor whonix-gateway-cli --vmsize 20G --target raw --build etc
Use qemu-img to convert the raw images to vmdk
qemu-img convert image.raw image.vmdk etc etc
Move or copy the .vmdk disks to a data store on ESXi
- From ESXi, create a new virtual switch for internal traffic. IMPORTANT: Delete the uplink by clicking the x! Create a new port group for internal traffic using the virtual switch you just created.
- Create a new virtual machine named Whonix-Workstation ™: Guest linux Debian 9 64bit, one network interface (change network to internal switch/portgroup), delete disk, add existing disk, select vmdk created for workstation, expand dropdown and select IDE controller. Boot the machine.
- Create a new virtual machine named Whonix-Gateway ™: Guest linux Debian 9 64bit, two network interfaces (leave first one default, add second and change to internal switch. Delete disk, add existing disk, select .vmdk created for gateway, expand dropdown and select IDE controller. Boot the machine. Note: This machine will have no WAN access unless one of the following actions is taken: addition of static route or modification of eth0 to DHCP.
Using VMWare Workstation as intermediary
If VMware Workstation is available, another option that works without manual extraction and repacking is to import both VMs to VMware Workstation, check that all settings are properly applied (as per the guide above) and then either export the VMs to ovf and import them on the ESXi server or, if the server is connected to the Workstation instance, migrate via VMware Workstation. This generally works out of the box, although the networking should be reviewed and isolated as per the guide above.
Harden VMware products
- Remove printer
- Disable 3D acceleration
- Remove CD/DVD drive
- Remove Floppy drive
- Remove USB controller (at least disable automatically connect new devices)
- Remove sound card
- Do not install VMware Tools or open-vm-tools (comfort vs. security). VMware Tools leak information towards the Host OS or Hypervisor.
One might wish to access the Whonix-Workstation ™ through SSH. Therefore you could add a second network adapter with Host-Only Networking. Beware about this adapter! This can cause information leakage!
If you install the proper routing or proxy software on your host computer, you can establish a connection between the host virtual Ethernet adapter and a physical network adapter on the host computer. This allows you, for example, to connect the virtual machine to a Token Ring or other non-Ethernet network. On a Windows 2000, Windows XP or Windows Server 2003 host computer, you can use host-only networking in combination with the Internet connection sharing feature in Windows to allow a virtual machine to use the host's dial-up networking adapter or other connection to the Internet. See your Windows documentation for details on configuring Internet connection sharing.
VMware upstream bug reports
- VMware bug report: failed to import .ova image
- VMware bug report: .ova image internal network becomes bridged network
- VirtualBox bug report Ticket #11160: .ova image created with VirtualBox, failed to import in VMware
(Windows 8 specific forum help thread:
No Tor/Internet connection with Windows 8 on VMware - Whonix-Gateway ™.)
(Black screen forum help thread:
No user support in comments. See Support.
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