Hacklog Volume 1 Anonymity: it security & Ethical Hacking Handbook

part and come back when you’re ready to continue.
Speaking  of  virtualization,  you  may  perform  this  process  with  a  Host
computer which is completely connected to the TOR network (in this case, any
Operating  System  will  work  fine)  and  connect  to  the  VPN  network  on  the
virtualized machine.
As  an  interesting  alternative,  you  may  also  use  a  hardware  router  like
P.O.R.T.A.L.
[56]
, allowing to directly connect a router to the TOR network, just
like the connection we mentioned with the VPN. However, this method is only
for the bravest.
5.2 VPN via TOR
This configuration follows this pattern:
Computer -> TOR -> VPN -> Internet
The user connects to the TOR network creating their secure network. From
here, they connect to the VPN hiding the TOR exit node IP, making it appear just
as a VPN user. If you perform a VPN network tunneling after you connected to
TOR,  you  will  let  your  ISP  know  you’re  using  the  TOR  network.  The  latter
creates  a  network  apart,  and  won’t  make  a  direct  tunneling  to  the  VPN,  which
instead  will  be  performed  separately,  thus  informing  the  ISP  that  you  are
connecting both to TOR and to a VPN.
Pro
-
You hide your identity from the VPN provider
-
You can access websites that block TOR exit-nodes
-
If you VPN is lost you will be protected by TOR nevertheless. You should
always prefer a VPN with the Kill Switch feature anyway.
Contro

---

-
You will tell your ISP you’re using both a VPN and TOR
-
You won’t access the deep web (.onion addresses et similia)
-
You will be in the NSA watch list spotlight
5.2.1 How to perform VPN via TOR
You  can  perform  this  type  of  connection  semi-permanently  with  a  router
compatible  with  the  OpenWRT
[57]
 or  dd-wrt
[58]
 firmware,  supporting  VPN
connections.  For  more  information  and  a  list  of  routers  compatible  with  those
firmware, visit the relevant official websites. Once you connected to the router,
you may navigate with ease using your preferred Tor client. Once again, you can
try  some  alternatives:  you  may  want  to  use  pre-configured  (or  self-configured)
distros, allowing to use the TOR network only to make external connections; the
correct procedure, i.e. on Tails, is described on the official page
[59]
.
5.3 TOR over TOR
On the TOR network chapter, we mentioned there is a very little chance that
the exit node, namely the final “layer” of the network going to the clearnet, may
track  our  actions.  Although  I  may  appear  as  paranoid,  I  want  to  introduce  a
method allowing to perform a TOR tunneling within another TOR network.
Even  if  this  operation  won’t  solve  the  exit  node  monitoring  problem,  it
allows  to  change  the  game  in  the  routing,  drastically  reducing  the  chances  of
identifying the request origin from the router itself.

---

5.3.1 Tortilla
Tortilla  is  a  program  which  reroutes  all  TCP  and  DNS  requests  within  the
TOR  node.  The  tool  is  deployed  with  pre-configured  and  independent  binaries
than the official ones, allowing to avoid any conflict. Using it with Tor Browser
or a TOR standalone version, you can perform a double tunneling, exactly as we
saw  between  VPN  an  TOR.  The  only  “limit”  is  that  it’s  only  available  for
Windows.
That  won’t  be  a  problem,  however,  since  you  can  use  Windows  as  a  Host
computer  and  run  a  Virtual  Machine  for  your  operations  (we  will  discuss  it  a
couple  of  chapters  later).  Tortilla  is  available  in  open  source  version  through
Github official channels
[60]
and pre-compiled from the official website
[61]
.
It’s very easy to use: get the TOR Expert Bundle from the official site first,
then  install  it  on  your  Operating  System  (even  better  on  a  USB  drive).  Launch
the  tor.exe  file  and  you’ll  get  to  the  command  prompt;  when  the  logs  show
Bootstrapped  100%  Done,  the  connection  to  TOR  circuit  is  complete,  so  you
will  be  ready  to  launch  the  tortilla.exe  client.  Remember  to  run  both  programs
with  admin  privileges;  some  Windows  versions  also  require  to  enable
unauthorized certificates – please refer to the Microsoft official guide
[62]
.
All  the  application  methods  for  VPN  over  TOR  circuits  also  apply  to  this
type of configuration.
5.3.2 Is TOR over TOR helpful?
Personally,  I  think  that  connecting  two  cascading  TOR  networks  won’t
ensure  any  benefit  in  terms  of  privacy,  compared  to  what  you  get  from  a  good
VPN. Using such configuration has to be considered as merely experimental and
not in line with the anonymity quality standards ensured by other types of combo
networks,  therefore  you  should  use  it  only  for  test  environments  and  for
educational purposes.

---

6. Local Resources
In this part of the document, we will cover the Local Resources, namely the
pool  of  software  and  virtual  objects  on  a  computer  that  may  somehow
compromise  the  anonymity  of  a  given  web  browser,  a  client  and  so  on.  When
you use a browser to navigate the web, you may unknowingly leave thousands of
data.  Now  we  are  going  to  provide  you  with  a  overview  for  each  resource  that
may expose the final user to the digital unblinding.
6.1 Private browsing
Built-in in any next generation browser,  the  Private  or  Incognito  mode  is  a
special  feature  allowing  you  to  temporarily  disable  all  the  data  which  may
compromise your anonymity, such as cookies, history, temporary files, sessions
and saved passwords.
6.1.1 How to enable the Private or Incognito mode
Each browser allow to enable the Private or Incognito mode using the proper
combination  of  keys.  For  your  convenience,  the  following  list  includes  all  the
keyboard shortcuts for the most popular online browsers: