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Practical
DROWNing
Putting a well known, highly computationally heavy crypto
attack into practice in real time.
Where What Who
Ruxmon Melbourne Practical DROWNing Tim Noise
tIMNOISE
• twitter/dnoiz1
• github/dnoiz1
• mIRC/dnz
• streetz/notorious D N Z
• tim@drkns.net
Blackhat sell out and V.I.L.E henchman
SECURESOCKETLAYER
• Sucked so bad v1 was never used
Emphasis on the first S - SSL
• v2 was released in 1995
• It sucked so bad, v3 was released in 1996
• It sucked so bad TLS
replaced it in 1998
• In 2016 we remembered v2
sucked and disabled it again
• We went back to SSLv2 in 2014
TransportLAYERSECURITYTurns out SSL was not good
• TLS 1.0 released in 99 - allows for
downgrade to SSL (thx)
• TLS 1.1 released in 2006 - Fixes CBC,
introduces explicit IV
• TLS 1.2 released in 2008
• 2011 TLS1.2 removes downgrade,
particularly to SSLv2
BasicHandshakesWere not blood-stacking just yet
ProtocolIMPLENTATIONSIts actually people who make code
RECENT-ISHATTACKS
• BEAST
• CRIME
• BREACH
• POODLE
• Logjam
• Heart bleed
• Cache bleed
• DROWN
Are we bored with codenames, logos and fancy websites yet?
NoteworthyCVEsOftheDAY
• CVE-2016-0800 / DROWN
• CVE-2016-0705 / Double Free in DSA
• CVE-2016-0798 / Memory Leak
• CVE-2016-0797 / Null Pointer deref/Heap corruption
• CVE-2016-0799 / Format String memory issues
• CVE-2016-0702 / Side Channel Attack
• CVE-2016-0703 / Divide and Conquer Key Recovery
• CVE-2016-0704 / Bleichenbacher oracle in SSLv2
Not all DROWN related, OpenSSL bugs with the same day 0
DROWNCVE-2016-0800
• Downgrade to SSLv2
• Bleichenbacher padding oracle
(CVE-2016-0704)
• Available to any port or service that
can negotiate SSLv2
• Compounded with CVE-2015-3197 to
select disabled ciphers
Decrypting RSA with Obsolete and Weakened eNcryption
VendorRESPONSE
• 0day was March 1, 2016
• Reported from upstream on February 22, 2016
• Immediately treated as High Touch
• Patches to OpenSSL were committed 

to git on 18th & 20th of February
• Other libraries followed shortly after
• RPMs published 0day along with RHSA
Cold sweats and beating day 0
HOWtoDROWNBetter than Bondi Rescue
HOWtoDROWN
• Attacker collects TLS RSA Key
Exchange messages
• Intercept cipher text containing 48
byte premaster secret to PKCS#1
v1.5 encoded messages of length to
SSLv2 oracle
• Perform the Bleichenbacher oracle
• Transform the data back into plain
text
Better than Bondi Rescue
DifficultyDROWNing
• Computational work for standard drown is 2^50
• requires observing 1000 TLS handshake
• requires performing 40,000 negations
• Under 8 hours and $440 using AWS EC2 Compute
nodes
Spin up all the CUDA cores
DOYOUCARE?
• Initial estimate at 11.5m (33% of scanned) of
HTTPS server
• Special DROWN 79% of the 11.5m
• Key reuse allows multiple servers to expose each
other (SMTP/IPMI/HTTPS etc)
Makes your KPIs look good and your CISO can sleep at night
SPECIALDROWN
• Special extra clear oracle
• Requires only 1/2 the number of connections
• Enabled by CVE-2016-703 / Divide-and-conquer
session key recovery
• Can be calculated in real time (under 1min on a single
core)
• Before the initial Handshake times out, allowing MITM
It only takes a toddler 30 seconds
TakeAWAY
• Install patched packages!
• Disable SSLv*
• Disable Shitty Ciphers
• Filter SSL negotiations on the network
Stuff to do when you get home
• Test for weak ciphers
• Test for SSL negotiation
• Test for Key Reuse
• Do more than test! MITM and Decrypt things
Defenders
Attackers
QUESTIONS?
Practical
DROWNing
Putting a well known, highly computationally heavy crypto
attack into practice in real time.
Where What Who
Ruxmon Melbourne Practical DROWNing Tim Noise
tIMNOISE
• twitter/dnoiz1
• github/dnoiz1
• mIRC/dnz
• streetz/notorious D N Z
• tim@drkns.net
Blackhat sell out and V.I.L.E henchman

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Practically DROWNing

  • 1. Practical DROWNing Putting a well known, highly computationally heavy crypto attack into practice in real time. Where What Who Ruxmon Melbourne Practical DROWNing Tim Noise
  • 2. tIMNOISE • twitter/dnoiz1 • github/dnoiz1 • mIRC/dnz • streetz/notorious D N Z • tim@drkns.net Blackhat sell out and V.I.L.E henchman
  • 3. SECURESOCKETLAYER • Sucked so bad v1 was never used Emphasis on the first S - SSL • v2 was released in 1995 • It sucked so bad, v3 was released in 1996 • It sucked so bad TLS replaced it in 1998 • In 2016 we remembered v2 sucked and disabled it again • We went back to SSLv2 in 2014
  • 4. TransportLAYERSECURITYTurns out SSL was not good • TLS 1.0 released in 99 - allows for downgrade to SSL (thx) • TLS 1.1 released in 2006 - Fixes CBC, introduces explicit IV • TLS 1.2 released in 2008 • 2011 TLS1.2 removes downgrade, particularly to SSLv2
  • 7. RECENT-ISHATTACKS • BEAST • CRIME • BREACH • POODLE • Logjam • Heart bleed • Cache bleed • DROWN Are we bored with codenames, logos and fancy websites yet?
  • 8. NoteworthyCVEsOftheDAY • CVE-2016-0800 / DROWN • CVE-2016-0705 / Double Free in DSA • CVE-2016-0798 / Memory Leak • CVE-2016-0797 / Null Pointer deref/Heap corruption • CVE-2016-0799 / Format String memory issues • CVE-2016-0702 / Side Channel Attack • CVE-2016-0703 / Divide and Conquer Key Recovery • CVE-2016-0704 / Bleichenbacher oracle in SSLv2 Not all DROWN related, OpenSSL bugs with the same day 0
  • 9. DROWNCVE-2016-0800 • Downgrade to SSLv2 • Bleichenbacher padding oracle (CVE-2016-0704) • Available to any port or service that can negotiate SSLv2 • Compounded with CVE-2015-3197 to select disabled ciphers Decrypting RSA with Obsolete and Weakened eNcryption
  • 10. VendorRESPONSE • 0day was March 1, 2016 • Reported from upstream on February 22, 2016 • Immediately treated as High Touch • Patches to OpenSSL were committed 
 to git on 18th & 20th of February • Other libraries followed shortly after • RPMs published 0day along with RHSA Cold sweats and beating day 0
  • 12. HOWtoDROWN • Attacker collects TLS RSA Key Exchange messages • Intercept cipher text containing 48 byte premaster secret to PKCS#1 v1.5 encoded messages of length to SSLv2 oracle • Perform the Bleichenbacher oracle • Transform the data back into plain text Better than Bondi Rescue
  • 13. DifficultyDROWNing • Computational work for standard drown is 2^50 • requires observing 1000 TLS handshake • requires performing 40,000 negations • Under 8 hours and $440 using AWS EC2 Compute nodes Spin up all the CUDA cores
  • 14. DOYOUCARE? • Initial estimate at 11.5m (33% of scanned) of HTTPS server • Special DROWN 79% of the 11.5m • Key reuse allows multiple servers to expose each other (SMTP/IPMI/HTTPS etc) Makes your KPIs look good and your CISO can sleep at night
  • 15. SPECIALDROWN • Special extra clear oracle • Requires only 1/2 the number of connections • Enabled by CVE-2016-703 / Divide-and-conquer session key recovery • Can be calculated in real time (under 1min on a single core) • Before the initial Handshake times out, allowing MITM It only takes a toddler 30 seconds
  • 16. TakeAWAY • Install patched packages! • Disable SSLv* • Disable Shitty Ciphers • Filter SSL negotiations on the network Stuff to do when you get home • Test for weak ciphers • Test for SSL negotiation • Test for Key Reuse • Do more than test! MITM and Decrypt things Defenders Attackers
  • 18. Practical DROWNing Putting a well known, highly computationally heavy crypto attack into practice in real time. Where What Who Ruxmon Melbourne Practical DROWNing Tim Noise
  • 19. tIMNOISE • twitter/dnoiz1 • github/dnoiz1 • mIRC/dnz • streetz/notorious D N Z • tim@drkns.net Blackhat sell out and V.I.L.E henchman