Hacklog Volume 1 Anonymity: it security & Ethical Hacking Handbook



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Hacklog Volume 1 Anonymity IT Security Ethical Hacking Handbook

Workstation.


Figure 49: Whonix operation diagram
As we can see in Figure 49, the Workstation is an environment that allows us
to  work  within  an  isolated  area  from  the  Gateway,  a  Virtual  Machine  already
designed  to  connect  via  Tor.  Nonetheless,  keep  in  mind  that  Whonix  has  the
same  security  limitations  as  we  mentioned  in  the  “Tor”  chapter;  additionally,
unlike  Tails,  it  is  not  a  ready-made  operating  system,  since  you  need  to  be
familiar with the GNU/Linux environment in order to use it.
The downside of such difference is the lack of some features that make Tails
more beneficial, like the following:
-
The lack of pre-configured Mac Spoofing
-
     
The lack of software “amnesia”, namely all the features aiming to remove
any information in the computer
-
The lack of metadata flushing
-
     
The lack of a complete encryption at the mail level, due to the backwards
compatibility with the SMTP protocol
-
and more
[148]
.
Some  of  these  gaps  can  be  filled  through  Qubes  virtualization,  others  by
applying  certain  techniques  we  already  mentioned  in  this  document.  However,
Whonix  and  Qubes  are  designed  to  be  used  from  a  fixed  machine,  the  price  to
pay when you want usability rather than safety (I can assure you such balance is
quite common in IT Security)
[149]
.
10.2.4 Subgraph OS
We can define Subgraph OS as the latest addition to Operating Systems for
privacy and anonymity. It’s still in Alpha, therefore just consider it as the draft of
what it will become in the future.
Developers  ensure  that  Subgraph  OS  will  be  a  groundbreaking  Operating
System, and they be right to some extent: it has been designed to be a fast OS
that  can  be  also  used  in  older  computers,  a  safe  system  for  users  who  are
concerned  about  their  privacy.  The  following  Figure  50  is  a  diagram  about  the


Subgraph OS structure.
Figure 50: Subgraph OS working diagram


10.2.4.1 Hardened like few others
Subgraph  OS  is  deployed  by  default  with  a  ready-compiled  kernel  of
Grsecurity, a set of patches ensuring a high level of security within the system.
Grsecurity  includes  PaX,  a  component  that  detects  many  different  OS  attacks,
like  buffer  overflows,  using  the  ASLR  technology  to  randomize  memory
allocations and obstruct any memory-level attack.
Subgraph  OS  also  implies  the  same  virtualization  concept  we  already  saw
with  Qubes  OS:  the  purpose  is  to  create  isolated  Sandboxes  that  cannot  inter-
communicate.  In  case  of  software  exploits,  the  Operating  System  won’t  be
impacted,  making  them  ineffective.  Such  process  in  ensured  by  OZ,  a  sandbox
framework  specifically  designed  for  Subgraph  OS.  If  you  wonder  if  Subgraph
OS supports file system encryption, the answer is: sure it does! Furthermore, it is
mandatory.
Most  of  the  tools  specifically  written  for  Subgraph  OS  are  high-level
(probably  interpreted  and  not  compiled)  so  they  can  resist  to  memory  attacks;
additionally,  the  majority  of  the  tools  considered  unnecessary  have  been
removed,  while  the  crucial  ones  have  been  integrated  with  security  measures
and, in some cases, even rewritten from scratch (like the default email client).
10.2.4.2 Network and Anonymity
Just like Qubes, we can find a networking domain: here it’s called Subgraph
Metaproxy and is accompanied by a Software Firewall. While the Firewall only
allows  the  applications  to  connect  to  the  Metaproxy,  the  latter  is  configured  to
connect  each  program  to  a  single  TOR  relay,  routing  the  connections  across
multiple  channels  and  minimizing  shared  information  in  the  network.  In  short,
navigating  the  web  and  writing  a  mail  will  imply  using  two  different  TOR
networks, and such prerogative will always be ensured by the Metaproxy. Back
to the firewall, users can temporarily or permanently grant the network access to
any software, removing any chance of System infection by a backdoor (unless it
is already residing in a whitelisted process). App whitelisting is performed both
by application name and target address; if an non-whitelisted application tries to
connect, the Firewall will just kill the connection.
As  you  understood,  Subgraph  OS  uses  the  TOR  network  to  communicate
with the external world: to be precise, it exclusively leverages the TOR network,


except  for  some  scenarios  where,  for  example,  a  direct  communication  to  the
visited portal is required (as a captive portal on a public WiFi network). Last but
not  least,  Subgraph  OS  provides  two  custom  software  for  communications
security.
-
     
Icedove,  a  Thunderbird-based  client,  powered  by  Enigmail  (GPG)  and
TorBirdy (Anonymity via Tor)
-
     
CoyIM,  a  XMPP  client  which  was  rewritten  from  scratch  to  avoid
memory-level exploits, also exclusively designed for the sole TOR network

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