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What	
  will	
  we	
  
                                                do	
  today? 	
  	
  

•  Penetra1on	
  Tes1ng	
  
   discussion	
             •  Non-­‐tech	
  view	
  
   –  Types	
  of	
  services	
        –  Dark	
  side?	
  
•  Social	
  Engineering	
          •  Interac1ve	
  
   –  Real-­‐life	
  examples	
        	
  
Penetra1on	
  
                                          Tes1ng 	
   	
  	
  

•  What?	
  
   –  Rude	
  word……	
  
   –  What	
  do	
  you	
  think?	
  
Breakdown 	
  
                                                          	
  

•    Build	
  Review	
                      •  WLAN	
  
•    Infrastructure	
                       •  Database	
  
•    Applica1on	
                           •  AD	
  
•    Code	
  Review	
  
•    Reverse	
  Engineering	
  
•    MVS	
  (PCI,	
  Int,	
  Ext	
  etc)	
  
Ops	
  J	
  	
  

•  Client	
  discussions	
        •  Report	
  
•  Proposal	
                     •  Invoice	
  
•  Acceptance	
  /	
  PO	
  
•  Rest	
  of	
  paperwork	
  
   (SOW	
  et	
  al)	
  
•  Resources	
  /	
  Schedule	
  
•  Delivery	
  
Oops	
  	
  L 	
  	
  

•  What	
  can	
  go	
  wrong?	
  
    –  DoS	
  
    –  Wrong	
  scope	
  
    –  Mis-­‐match	
  resources	
  
    –  Dissa1sfied	
  clients	
  
    –  Non-­‐payment	
  
Social	
  
                                               Engineering	
  
                                                   (SE)	
  	
  
•  Art	
  of	
  decep1on?	
  
    –  Manipula1on	
  
    –  Disclosure	
  
•  What	
  do	
  you	
  see	
  as	
  SE?	
  
    –  Examples	
  
SE:	
  Anatomy	
  	
  

•  Agree	
  scope	
  
   –  What	
  is	
  in?	
  
   –  What	
  is	
  out?	
  MAKE	
  THIS	
  VERY	
  CLEAR	
  
•  Reconnaissance	
  
   –  Onsite	
  
   –  Web	
  
   –  News	
  
SE:	
  Anatomy	
  
                                                       Cont’d	
  	
  

•  Plan	
  based	
  on	
  reconnaissance	
  
   –  Approximate	
  idea	
  of	
  execu1on	
  
   –  Poten1al	
  back-­‐up	
  plans	
  of	
  delivery	
  failure	
  
   –  Changing	
  course	
  based	
  on	
  scenario	
  
SE:	
  
                                                      Characteris1cs	
  
                       	
  
                                                         &	
  Tools	
  
                                                         	
  
         CHARACTERISTICS	
                                TOOLS	
  
•      Guts	
                            •      Internet	
  
•      Keep	
  calm	
                    •      Google	
  Earth	
  
•      Think	
  on	
  your	
  feet	
     •      Charm	
  
•      Change	
  tac1cs	
  whilst	
      •      Manners	
  
       keeping	
  your	
  wits	
         •      Gadgets	
  (phone,	
  
       about	
  you	
                           camera)	
  
	
                                       	
  
                                         	
  
SE:	
  
                                         Outcome	
  /	
  
                                          Results	
  
•  Report	
  
•  Evidence	
  (MOST	
  IMPORTANT)	
  
	
  
	
  
SE:	
  Example	
  


•  Crea1ng	
  a	
  fake	
  email	
  account	
  with	
  a	
  real	
  
   person’s	
  name.	
  	
  
•  Ellen	
  belongs	
  to	
  a	
  company	
  loosely	
  
   affiliated	
  with	
  the	
  target.	
  
SE:	
  Example	
  
                                                             Cont’d	
  

•  Sending	
  an	
  email	
  from	
  “Ellen”	
  to	
  many	
  
   hundreds	
  of	
  employees	
  of	
  the	
  target	
  
   company.	
  	
  
•  The	
  email	
  contents	
  is	
  based	
  on	
  a	
  real	
  event	
  
   that	
  the	
  target	
  company	
  held	
  (gleaned	
  from	
  
   their	
  news	
  website).	
  	
  
•  The	
  email	
  encourages	
  people	
  to	
  visit	
  a	
  
   website,	
  which	
  appears	
  to	
  be	
  legi1mate.	
  	
  
SE:	
  Example	
  
                                                                  Cont’d	
  

	
  
       •  The	
  website	
  is	
  a	
  duplicate	
  of	
  the	
  target	
  
          company	
  website,	
  with	
  a	
  few	
  minor	
  
          modifica1ons	
  to	
  go	
  along	
  with	
  the	
  farcical	
  
          story	
  from	
  the	
  email.	
  	
  
       •  The	
  page	
  a]empts	
  to	
  run	
  a	
  Java	
  applet	
  
          (next	
  slide).	
  
SE:	
  Example	
  
                                                                    Cont’d	
  

	
  
       •  Should	
  the	
  user	
  click	
  yes	
  to	
  running	
  the	
  
          applet	
  from	
  the	
  site,	
  some	
  hos1le	
  Java	
  will	
  
          execute	
  which	
  will	
  compromise	
  the	
  
          machine,	
  and	
  give	
  the	
  a]acker	
  full	
  control	
  
          (as	
  in	
  next	
  slide)	
  
SE:	
  Example	
  
                                                              Cont’d	
  

	
  

       •  Pwnd	
  ;)	
  	
  
       •  Logs	
  of	
  people	
  visi1ng	
  the	
  site	
  
SE:	
  Example	
  
                                                              Cont’d	
  

•  Oddly	
  enough,	
  a	
  real	
  employee	
  (Fred)	
  
   replied	
  to	
  the	
  a]acker	
  with	
  real	
  comments	
  
   about	
  the	
  site.	
  	
  
•  This	
  was	
  useful	
  as	
  it	
  gave	
  us	
  his	
  name	
  /	
  
   email	
  signature	
  etc.	
  which	
  could	
  be	
  used	
  to	
  
   create	
  another	
  fake	
  email	
  account	
  abusing	
  
   his	
  informa1on.	
  
SE:	
  Example	
  
                                                                Cont’d	
  

	
  
       Crea1ng	
  a	
  fake	
  account	
  for	
  target	
  company	
  
       employee	
  Fred	
  
SE:	
  Example	
  
                                                                 Cont’d	
  

•  The	
  en1re	
  email	
  is	
  forged	
  from	
  Fred,	
  but	
  it	
  
   appears	
  as	
  though	
  he	
  is	
  forwarding	
  on	
  an	
  
   email	
  –	
  which	
  is	
  made	
  to	
  look	
  like	
  it	
  came	
  
   from	
  a	
  real	
  employee.	
  	
  
•  Here	
  we	
  abuse	
  the	
  chain	
  of	
  trust.	
  	
  
•  The	
  email	
  encourages	
  users	
  to	
  go	
  to	
  a	
  
   Microsob	
  website	
  to	
  download	
  an	
  urgent	
  
   update	
  
SE:	
  Example	
  
                                                                     Cont’d	
  
	
  
	
  
       •  The	
  a]acker	
  has	
  downloaded	
  a	
  real	
  MS	
  
          update,	
  but	
  sneakily	
  inserted	
  some	
  hos1le	
  
          code	
  (The	
  “hot”	
  file).	
  	
  
       •  This	
  is	
  hosted	
  on	
  a	
  fake	
  MS	
  website	
  (next	
  
          slide)	
  
SE:	
  Example	
  
                                                                 Cont’d	
  

	
  

       Looks	
  legit?	
  Almost	
  too	
  good	
  to	
  be	
  true.	
  
SE:	
  Example	
  
                                                                       Cont’d	
  

	
     •  Here	
  we	
  see	
  a	
  user	
  downloading	
  and	
  
          running	
  the	
  file-­‐	
  the	
  result	
  of	
  which	
  his	
  AV	
  
          being	
  killed,	
  a	
  screenshot	
  of	
  his	
  desktop	
  
          being	
  taken,	
  and	
  full	
  control	
  of	
  his	
  machine	
  
          given	
  to	
  the	
  a]acker.	
  
       •  Game	
  over.	
  
  	
  

   	
  
   	
  
Ques1ons	
  
Contact	
  
                                        Details	
  


Name:	
  Yve]e	
  du	
  Toit	
  
Email:	
  	
  yve]e@sensepost.com	
  

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Penetration Testing and Social Engineering Overview

  • 1. What  will  we   do  today?     •  Penetra1on  Tes1ng   discussion   •  Non-­‐tech  view   –  Types  of  services   –  Dark  side?   •  Social  Engineering   •  Interac1ve   –  Real-­‐life  examples    
  • 2. Penetra1on   Tes1ng       •  What?   –  Rude  word……   –  What  do  you  think?  
  • 3. Breakdown     •  Build  Review   •  WLAN   •  Infrastructure   •  Database   •  Applica1on   •  AD   •  Code  Review   •  Reverse  Engineering   •  MVS  (PCI,  Int,  Ext  etc)  
  • 4. Ops  J     •  Client  discussions   •  Report   •  Proposal   •  Invoice   •  Acceptance  /  PO   •  Rest  of  paperwork   (SOW  et  al)   •  Resources  /  Schedule   •  Delivery  
  • 5. Oops    L     •  What  can  go  wrong?   –  DoS   –  Wrong  scope   –  Mis-­‐match  resources   –  Dissa1sfied  clients   –  Non-­‐payment  
  • 6. Social   Engineering   (SE)     •  Art  of  decep1on?   –  Manipula1on   –  Disclosure   •  What  do  you  see  as  SE?   –  Examples  
  • 7. SE:  Anatomy     •  Agree  scope   –  What  is  in?   –  What  is  out?  MAKE  THIS  VERY  CLEAR   •  Reconnaissance   –  Onsite   –  Web   –  News  
  • 8. SE:  Anatomy   Cont’d     •  Plan  based  on  reconnaissance   –  Approximate  idea  of  execu1on   –  Poten1al  back-­‐up  plans  of  delivery  failure   –  Changing  course  based  on  scenario  
  • 9. SE:   Characteris1cs     &  Tools     CHARACTERISTICS   TOOLS   •  Guts   •  Internet   •  Keep  calm   •  Google  Earth   •  Think  on  your  feet   •  Charm   •  Change  tac1cs  whilst   •  Manners   keeping  your  wits   •  Gadgets  (phone,   about  you   camera)        
  • 10. SE:   Outcome  /   Results   •  Report   •  Evidence  (MOST  IMPORTANT)      
  • 11. SE:  Example   •  Crea1ng  a  fake  email  account  with  a  real   person’s  name.     •  Ellen  belongs  to  a  company  loosely   affiliated  with  the  target.  
  • 12. SE:  Example   Cont’d   •  Sending  an  email  from  “Ellen”  to  many   hundreds  of  employees  of  the  target   company.     •  The  email  contents  is  based  on  a  real  event   that  the  target  company  held  (gleaned  from   their  news  website).     •  The  email  encourages  people  to  visit  a   website,  which  appears  to  be  legi1mate.    
  • 13. SE:  Example   Cont’d     •  The  website  is  a  duplicate  of  the  target   company  website,  with  a  few  minor   modifica1ons  to  go  along  with  the  farcical   story  from  the  email.     •  The  page  a]empts  to  run  a  Java  applet   (next  slide).  
  • 14. SE:  Example   Cont’d     •  Should  the  user  click  yes  to  running  the   applet  from  the  site,  some  hos1le  Java  will   execute  which  will  compromise  the   machine,  and  give  the  a]acker  full  control   (as  in  next  slide)  
  • 15. SE:  Example   Cont’d     •  Pwnd  ;)     •  Logs  of  people  visi1ng  the  site  
  • 16. SE:  Example   Cont’d   •  Oddly  enough,  a  real  employee  (Fred)   replied  to  the  a]acker  with  real  comments   about  the  site.     •  This  was  useful  as  it  gave  us  his  name  /   email  signature  etc.  which  could  be  used  to   create  another  fake  email  account  abusing   his  informa1on.  
  • 17. SE:  Example   Cont’d     Crea1ng  a  fake  account  for  target  company   employee  Fred  
  • 18. SE:  Example   Cont’d   •  The  en1re  email  is  forged  from  Fred,  but  it   appears  as  though  he  is  forwarding  on  an   email  –  which  is  made  to  look  like  it  came   from  a  real  employee.     •  Here  we  abuse  the  chain  of  trust.     •  The  email  encourages  users  to  go  to  a   Microsob  website  to  download  an  urgent   update  
  • 19. SE:  Example   Cont’d       •  The  a]acker  has  downloaded  a  real  MS   update,  but  sneakily  inserted  some  hos1le   code  (The  “hot”  file).     •  This  is  hosted  on  a  fake  MS  website  (next   slide)  
  • 20. SE:  Example   Cont’d     Looks  legit?  Almost  too  good  to  be  true.  
  • 21. SE:  Example   Cont’d     •  Here  we  see  a  user  downloading  and   running  the  file-­‐  the  result  of  which  his  AV   being  killed,  a  screenshot  of  his  desktop   being  taken,  and  full  control  of  his  machine   given  to  the  a]acker.   •  Game  over.  
  • 22.         Ques1ons  
  • 23. Contact   Details   Name:  Yve]e  du  Toit   Email:    yve]e@sensepost.com