Chaining Anonymizing Gateways
Only experts should attempt these configurations!
By default, all Whonix-Workstation traffic is forced through Whonix-Gateway. Alternatively, a chain of anonymizing gateways can be built, with sample tunnel configurations outlined below.
Before attempting complex tunnel configurations, the following basic knowledge is required:
This Inspiration resource may also be useful.
## chain: Whonix-Workstation -> VPN-Gateway -> Whonix-Gateway -> clearnet ## connection scheme: user -> VPN -> Tor -> Internet
## chain: Whonix-Workstation -> Whonix-Gateway -> VPN-Gateway -> clearnet ## connection scheme: user -> Tor -> VPN -> Internet
Pre- and Post-Tor-VPN
## chain: Whonix-Workstation -> VPN-Gateway -> Whonix-Gateway -> VPN-Gateway -> Internet ## connection scheme: user -> VPN -> Tor -> VPN -> Internet
Whonix is not limited to VPN-Gateways; the VPN can be replaced with a Proxy-Gateway.
## chain: Whonix-Workstation -> Proxy-Gateway -> Whonix-Gateway -> clearnet ## connection scheme: user -> Tor -> Proxy -> Internet
Other Connection Schemes
Virtually any combination is possible: a Post-Tor-Proxy; a Pre/Post-Tor-SSH; or the proxy being replaced with JonDo or perhaps I2P.
Always remember that the connection will be created in reverse order; see the example below. 
## chain: Whonix-Workstation -> Proxy-Gateway -> Whonix-Gateway -> VPN-Gateway -> clearnet ## connection scheme: user -> VPN -> Tor -> Proxy -> Internet
Upon reflection, it becomes clear why the connection happens in reverse order:
- Whonix-Workstation has no option but to pass through the Proxy-Gateway.
- The Proxy-Gateway has no option but to pass through Whonix-Gateway.
- In this case, the last element in the chain is the VPN-Gateway, which must obviously connect through clearnet.
Thus, the VPN-Gateway uses clearnet, the Whonix-Gateway uses the VPN-Gateway to connect, the Proxy-Gateway uses Whonix-Gateway to connect, and Whonix-Workstation uses the Proxy-Gateway to connect. Since the Proxy-Gateway can only pass through Whonix-Gateway followed by the VPN-Gateway, it is clear why it will be the last hop in front of the destination server.
Whether these combinations make sense in terms of security and anonymity is hotly debated and depends on the user's personal threat model, see Tor plus VPN or Proxy.
Users must also understand and be capable of editing /etc/network/interfaces on Whonix-Gateway and/or on Whonix-Workstation. In the case of Non-Qubes-Whonix, this refers to the virtual internal network name in VirtualBox settings.
This process is generally difficult because there are no other anonymizing gateways (VPN / JonDo / I2P / Proxy / SSH / VPN) available for download in Whonix, just the Whonix-Gateway which uses Tor to anonymize traffic. Users often have to look for instructions and/or build an anonymizing gateway themselves. 
For a VPN-Gateway, see also:
- "Internet" below refers to the destination server (a website for example).
- There are some instructions for a pfSense based VPN-Gateway which can be found with search engines, but it is untested for leaks.
Whonix Chaining Anonymizing Gateways wiki page Copyright (C) Amnesia <amnesia at boum dot org>
Whonix Chaining Anonymizing Gateways wiki page Copyright (C) 2012 - 2018 ENCRYPTED SUPPORT LP <email@example.com>
This program comes with ABSOLUTELY NO WARRANTY; for details see the wiki source code.
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