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Building	
  a	
  Rube	
  Goldberg	
  
Applica3on	
  Security	
  Program	
  
SOURCE	
  Boston	
  2011	
  	
  
Wendy Nather
The 451 Group
The	
  451	
  Group	
  

                          451	
  Research	
  is	
  focused	
  on	
  the	
  business	
  of	
  enterprise	
  IT	
  
                          innova3on.	
  The	
  company’s	
  analysts	
  provide	
  cri3cal	
  and	
  3mely	
  
                          insight	
  into	
  the	
  compe33ve	
  dynamics	
  of	
  innova3on	
  in	
  emerging	
  
                          technology	
  segments.	
  


                          Tier1	
  Research	
  is	
  a	
  single-­‐source	
  research	
  and	
  advisory	
  firm	
  covering	
  
                          the	
  mul3-­‐tenant	
  datacenter,	
  hos3ng,	
  IT	
  and	
  cloud-­‐compu3ng	
  sectors,	
  
                          blending	
  the	
  best	
  of	
  industry	
  and	
  financial	
  research.	
  	
  


                          The	
  Up3me	
  Ins3tute	
  is	
  ‘ The	
  Global	
  Data	
  Center	
  Authority’	
  and	
  a	
  
                          pioneer	
  in	
  the	
  crea3on	
  and	
  facilita3on	
  of	
  end-­‐user	
  knowledge	
  
                          communi3es	
  to	
  improve	
  reliability	
  and	
  uninterrup3ble	
  availability	
  	
  
                          in	
  datacenter	
  facili3es.	
  

                          TheInfoPro	
  is	
  a	
  leading	
  IT	
  advisory	
  and	
  research	
  firm	
  that	
  provides	
  
                          real-­‐world	
  perspec3ves	
  on	
  the	
  customer	
  and	
  market	
  dynamics	
  of	
  the	
  
                          enterprise	
  informa3on	
  technology	
  landscape,	
  harnessing	
  the	
  
                          collec3ve	
  knowledge	
  and	
  insight	
  of	
  leading	
  IT	
  organiza3ons	
  
                          worldwide.	
  

                          ChangeWave	
  Research	
  is	
  a	
  research	
  firm	
  that	
  iden3fies	
  and	
  quan3fies	
  
                          ‘change’	
  in	
  consumer	
  spending	
  behavior,	
  corporate	
  purchasing,	
  and	
  
                          industry,	
  company	
  and	
  technology	
  trends.	
  	
  
The	
  Platonic	
  Ideal	
  of	
  an	
  applica3on	
  security	
  program	
  
The	
  Platonic	
  Ideal	
  of	
  an	
  applica3on	
  security	
  program	
  
The	
  Platonic	
  Ideal	
  of	
  an	
  applica3on	
  security	
  remedia3on	
  project	
  
The	
  Platonic	
  Ideal	
  of	
  an	
  applica3on	
  security	
  remedia3on	
  project	
  
The	
  Platonic	
  Ideal	
  of	
  an	
  applica3on	
  security	
  remedia3on	
  project	
  
How	
  it	
  really	
  happens	
  

  Training	
  
    •  Onsite	
  classes	
  are	
  expensive	
  
    •  Offsite	
  classes	
  are	
  even	
  more	
  expensive	
  
    •  You	
  can’t	
  pay	
  to	
  train	
  contractors	
  
    •  The	
  most	
  important	
  developers	
  can’t	
  make	
  it	
  to	
  the	
  classes	
  
    •  Nobody	
  fires	
  up	
  the	
  e-­‐learning	
  applica3on	
  
    •  E-­‐learning	
  doesn’t	
  teach	
  developers	
  half	
  of	
  what	
  they	
  need	
  to	
  know	
  
How	
  it	
  really	
  works	
  

  Threat	
  modeling	
  and	
  security	
  requirements	
  
   •  It’s	
  not	
  in	
  any	
  story	
  
   •  Security	
  isn’t	
  just	
  in	
  the	
  applica3on	
  design	
  
   •  Developers	
  make	
  bad	
  assump3ons	
  about	
  the	
  environment	
  for	
  their	
  
      applica3ons	
  
   •  YOU	
  try	
  wri3ng	
  down	
  every	
  single	
  security	
  requirement	
  
   •  Security	
  requirements	
  are	
  new	
  and	
  can	
  be	
  every	
  bit	
  as	
  disrup3ve	
  as	
  
      new	
  func3onality	
  
   •  Func3onal	
  requirements	
  change	
  mid-­‐project;	
  threat	
  modeling	
  and	
  
      security	
  requirements	
  have	
  to	
  be	
  re-­‐visited	
  
   •  Developers	
  will	
  ask	
  for	
  excep3ons	
  to	
  security	
  requirements	
  and	
  you	
  
      have	
  to	
  grant	
  them	
  and	
  track	
  them	
  
How	
  it	
  really	
  works	
  

  Peer	
  review	
  and	
  scanning	
  in	
  development	
  
   •  Not	
  every	
  tool	
  will	
  scan	
  an	
  app	
  that	
  isn’t	
  built	
  
   •  Itera3ve	
  scanning	
  is	
  what	
  the	
  developer	
  wants	
  to	
  do,	
  but	
  it	
  takes	
  too	
  
      long	
  
   •  The	
  development	
  environment	
  is	
  different	
  from	
  produc3on	
  
   •  The	
  security	
  team	
  becomes	
  a	
  boleneck	
  as	
  they	
  field	
  ques3ons	
  and	
  help	
  
      write	
  the	
  code	
  
   •  There	
  are	
  s3ll	
  dependencies	
  on	
  other	
  insecure	
  applica3ons	
  and	
  insecure	
  
      libraries	
  
   •  Here	
  There	
  Be	
  Deadlines	
  
How	
  it	
  really	
  works	
  

  QA	
  tes3ng	
  
   •  They	
  don’t	
  want	
  security	
  tes3ng	
  messing	
  with	
  their	
  tes3ng	
  results	
  
   •  Itera3ve	
  scan-­‐fix-­‐rescan	
  cycle	
  too	
  short	
  for	
  many	
  tools	
  
   •  QA	
  thinks	
  that	
  “security	
  tes3ng”	
  means	
  tes3ng	
  to	
  see	
  if	
  the	
  login	
  
      works	
  
   •  Verbose	
  error	
  messages	
  are	
  needed	
  for	
  troubleshoo3ng	
  
   •  Test	
  environment	
  s3ll	
  isn’t	
  the	
  same	
  as	
  in	
  produc3on	
  
   •  Those	
  short	
  deadlines	
  again	
  
How	
  it	
  really	
  works	
  

  The	
  Budget	
  Issue	
  
   •  Once	
  a	
  project	
  is	
  done,	
  it’s	
  done	
  
   •  Nobody	
  keeps	
  staff	
  siang	
  around	
  wai3ng,	
  in	
  case	
  there’s	
  an	
  
      applica3on	
  that	
  needs	
  remedia3ng	
  
   •  Remedia3on	
  of	
  an	
  app	
  can	
  be	
  a	
  full	
  project	
  in	
  and	
  of	
  itself	
  
   •  The	
  CIO	
  never	
  intended	
  to	
  touch	
  that	
  applica3on	
  again	
  
   •  Project	
  managers	
  rarely	
  budget	
  for	
  QA	
  3me,	
  much	
  less	
  for	
  security	
  
      tes3ng	
  

  Boom	
  line:	
  	
  they	
  don’t	
  see	
  the	
  risk	
  
Scanner	
  1 	
  	
  



Scanner	
  2	
  



Scanner	
  3	
  
Scanner	
  1	
  
Scanner	
  2	
  
The	
  environment	
  



                                             Single	
  sign-­‐
                                                 on	
  



                          Roles	
  and	
                          Roles	
  and	
  
                         en3tlements	
                           en3tlements	
  




                 App1	
                  App2	
                     App60	
  
Scanner	
  3	
  
Story	
  of	
  a	
  legacy	
  applica3on	
  
The	
  moral	
  of	
  the	
  story	
  

  Budget	
  isn’t	
  enough	
  (even	
  when	
  there’s	
  enough	
  budget)	
  
  Have	
  your	
  pieces	
  placed	
  in	
  the	
  right	
  order	
  
  Timing	
  is	
  everything	
  
  A	
  “15-­‐minute	
  fix”	
  –	
  isn’t	
  
  Running	
  an	
  applica3on	
  security	
  program	
  is	
  as	
  much	
  about	
  social	
  
   engineering	
  as	
  it	
  is	
  about	
  the	
  technical	
  side	
  
Thank	
  You	
  

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Wendy Nather - Building a Rube Goldberg Application Security Program

  • 1. Building  a  Rube  Goldberg   Applica3on  Security  Program   SOURCE  Boston  2011     Wendy Nather The 451 Group
  • 2. The  451  Group   451  Research  is  focused  on  the  business  of  enterprise  IT   innova3on.  The  company’s  analysts  provide  cri3cal  and  3mely   insight  into  the  compe33ve  dynamics  of  innova3on  in  emerging   technology  segments.   Tier1  Research  is  a  single-­‐source  research  and  advisory  firm  covering   the  mul3-­‐tenant  datacenter,  hos3ng,  IT  and  cloud-­‐compu3ng  sectors,   blending  the  best  of  industry  and  financial  research.     The  Up3me  Ins3tute  is  ‘ The  Global  Data  Center  Authority’  and  a   pioneer  in  the  crea3on  and  facilita3on  of  end-­‐user  knowledge   communi3es  to  improve  reliability  and  uninterrup3ble  availability     in  datacenter  facili3es.   TheInfoPro  is  a  leading  IT  advisory  and  research  firm  that  provides   real-­‐world  perspec3ves  on  the  customer  and  market  dynamics  of  the   enterprise  informa3on  technology  landscape,  harnessing  the   collec3ve  knowledge  and  insight  of  leading  IT  organiza3ons   worldwide.   ChangeWave  Research  is  a  research  firm  that  iden3fies  and  quan3fies   ‘change’  in  consumer  spending  behavior,  corporate  purchasing,  and   industry,  company  and  technology  trends.    
  • 3. The  Platonic  Ideal  of  an  applica3on  security  program  
  • 4. The  Platonic  Ideal  of  an  applica3on  security  program  
  • 5. The  Platonic  Ideal  of  an  applica3on  security  remedia3on  project  
  • 6. The  Platonic  Ideal  of  an  applica3on  security  remedia3on  project  
  • 7. The  Platonic  Ideal  of  an  applica3on  security  remedia3on  project  
  • 8. How  it  really  happens     Training   •  Onsite  classes  are  expensive   •  Offsite  classes  are  even  more  expensive   •  You  can’t  pay  to  train  contractors   •  The  most  important  developers  can’t  make  it  to  the  classes   •  Nobody  fires  up  the  e-­‐learning  applica3on   •  E-­‐learning  doesn’t  teach  developers  half  of  what  they  need  to  know  
  • 9. How  it  really  works     Threat  modeling  and  security  requirements   •  It’s  not  in  any  story   •  Security  isn’t  just  in  the  applica3on  design   •  Developers  make  bad  assump3ons  about  the  environment  for  their   applica3ons   •  YOU  try  wri3ng  down  every  single  security  requirement   •  Security  requirements  are  new  and  can  be  every  bit  as  disrup3ve  as   new  func3onality   •  Func3onal  requirements  change  mid-­‐project;  threat  modeling  and   security  requirements  have  to  be  re-­‐visited   •  Developers  will  ask  for  excep3ons  to  security  requirements  and  you   have  to  grant  them  and  track  them  
  • 10. How  it  really  works     Peer  review  and  scanning  in  development   •  Not  every  tool  will  scan  an  app  that  isn’t  built   •  Itera3ve  scanning  is  what  the  developer  wants  to  do,  but  it  takes  too   long   •  The  development  environment  is  different  from  produc3on   •  The  security  team  becomes  a  boleneck  as  they  field  ques3ons  and  help   write  the  code   •  There  are  s3ll  dependencies  on  other  insecure  applica3ons  and  insecure   libraries   •  Here  There  Be  Deadlines  
  • 11. How  it  really  works     QA  tes3ng   •  They  don’t  want  security  tes3ng  messing  with  their  tes3ng  results   •  Itera3ve  scan-­‐fix-­‐rescan  cycle  too  short  for  many  tools   •  QA  thinks  that  “security  tes3ng”  means  tes3ng  to  see  if  the  login   works   •  Verbose  error  messages  are  needed  for  troubleshoo3ng   •  Test  environment  s3ll  isn’t  the  same  as  in  produc3on   •  Those  short  deadlines  again  
  • 12. How  it  really  works     The  Budget  Issue   •  Once  a  project  is  done,  it’s  done   •  Nobody  keeps  staff  siang  around  wai3ng,  in  case  there’s  an   applica3on  that  needs  remedia3ng   •  Remedia3on  of  an  app  can  be  a  full  project  in  and  of  itself   •  The  CIO  never  intended  to  touch  that  applica3on  again   •  Project  managers  rarely  budget  for  QA  3me,  much  less  for  security   tes3ng     Boom  line:    they  don’t  see  the  risk  
  • 13. Scanner  1     Scanner  2   Scanner  3  
  • 16. The  environment   Single  sign-­‐ on   Roles  and   Roles  and   en3tlements   en3tlements   App1   App2   App60  
  • 18.
  • 19. Story  of  a  legacy  applica3on  
  • 20. The  moral  of  the  story     Budget  isn’t  enough  (even  when  there’s  enough  budget)     Have  your  pieces  placed  in  the  right  order     Timing  is  everything     A  “15-­‐minute  fix”  –  isn’t     Running  an  applica3on  security  program  is  as  much  about  social   engineering  as  it  is  about  the  technical  side