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#RSAC
Kenneth Geers
Five InfoSec Lessons from the
Great Generals of the Ancient
World
MASH-F03
Ambassador
NATO Cooperative Cyber Defence
Centre of Excellence
@kennethgeers
Spencer Wolfe
Head Security Research Writer
ZeroFOX
@wolfesp18
#RSAC
Introduction
“The bravest among us are surely those who have the clearest
vision of what is before them, danger and glory alike, and yet
notwithstanding, go out to meet it.”
-Thucydides, The History of the Peloponnesian War
#RSAC
What’s This Talk About, Again?
3
“Come then and let us pass a
leisure hour in storytelling,
and our stories shall become
the education of our heroes.”
--Plato, The Republic
#RSAC
Mappetizer
4
Phase 1: Greece
Phase 2:
Alexander the Great
Phase 3:
Roman Empire
#RSAC
Close Up: Greece
5
P E R S I A
SPARTA
ATHENS
THEBES
MACEDON
#RSAC
The History of Greece in a Single Slide
ROME??
POWER
YEAR (BC)
Athenian Golden Age
(Periclean Athens)
Spartan
Hegemony
Battle of
Salamis (479)
Theban
Hegemony
Battle of
Aegospotami
(405)
Battle of
Leuctra (371)
Battle of
Chaeronea
(338)
Battle of
Gaugamela
(331)
Conquests of
Alexander the
Great
Persia =
Athens =
Sparta =
Thebes =
Macedon =
Key
Rise of
Macedon
#RSAC
Lesson 1: Choose Your Battlefield
Thermopylae, Salamis and the Greeks Fighting on Their Own Turf
#RSAC
Leonidas & Themistocles
8
Warner Brothers Pictures, 2006 Warner Brothers Pictures, 2014
#RSAC
The Greco-Persian Wars: 480-479
9
• Persia, under Xerxes, invades
in Greece in 480
• Leonidas & the Spartans
defend Thermopylae to the
last man
• In 479, the Persian navy is
decisively defeated at Salamis
by a Greek fleet led by
Themistocles
• Xerxes leaves, the rest of his
army is destroyed at Plataea
mapbox.com
#RSAC
Thermopylae: The Bottleneck
10
“The Persians were roughly
handled by the Spartans, since
they used shorter spears than
the Greeks and could not use
their numbers fighting in a
narrow space. The Spartans
fought memorably, showing
themselves skilled fighters
amidst unskilled.”
-Herodotus, Histories (VII, 211)
Brian Martens – 11/8/2012
livius.org
#RSAC
Salamis: Same Tactic, Different Element
11
“By engaging many ships
with our few ships in the
strait, we shall win a great
victory. If the war turns out
reasonably, it is to our
advantage to fight in the
strait and to their advantage
to fight in the open ocean.”
- Themistocles, from:
Herodotus, Histories (VII, 60)
www.arsbellica.it
#RSAC
Who cares? You do.POWER
YEAR (BC)
Battle of
Salamis (479)
Persia =
Athens =
Sparta =
Thebes =
KeyThings that might
not have happened:
• Democracy
• Greek philosophy (Socrates, Plato, Aristotle)
• Greek literature (The Iliad, The Odyssey)
• Greek theater (Aeschylus, Sophocles, Euripides,
Aristophanes)
• Greek history (Herodotus, Thucydides, Xenophon)
• Greek art
• Greek medicine
• The Rise of Rome
• Christianity
• Western Civilization….?
Athenian Golden Age
(Periclean Athens)
#RSAC
What this means for you
13
You know your system better
than anyone, so…
Where is your Thermopylae?
Where is your Salamis?
Where do you choose to fight?
#RSAC
Lesson #1: Choose your battlefield
• Cyber terrain
• USG: decrease # of nets, homogenize
• Risk: all eggs in one basket
• Utopia vs. Big Brother
• Elections and surveillance
• Belarus, China, Russia, Zimbabwe
• Creativity on cyber defense
• Code Red worm vs. MS IIS web server (2001)
• Bot army: 359,000 infected servers
• DoS Target: White House website
• Techies “blackholed” the attack
#RSAC
Lesson #1: Choose your battlefield
• Strategy before tactics
• Crown jewels
• Traffic analysis
• Alice, Bob, Charlie
• Old paradigm
• Defined perimeter
• New paradigm
• Undefined perimeter, social media
• Compartmentalization
• Assume insider / penetration
#RSAC
Lesson 2: Be Original
Epaminondas Beats the “Unbeatable” Spartans
#RSAC
Greece divided (again)
17
Greece after 479
• 479-431: Athenian Golden Age
• 431-405: Peloponnesian War,
fought between Athens and Sparta
• Sparta defeats Athens
• 405-371: Spartan Hegemony
• 371: Thebes defeats Sparta at the
Battle of Leuctra
#RSAC
The Greek Phalanx
18
• Rounds shields called hoplons
• Overhand spear
• Short sword called a xiphos
• Shields overlap one another, forming a
solid block
• Opposing forces clash and try to push
one another off the field
• 8-12 men deep
Ancientgreekbattles.net
#RSAC
Oblique Formation: Leuctra, 371BC
19
“The Spartans led each half-company
three files abreast, and this resulted in
the phalanx being not more than twelve
men deep. The Thebans, however, were
massed not less than fifty shields deep,
calculating that if they conquered that
part of the army around the king, all the
rest of it would be easy to overcome.”
- Xenophon, Hellenica
Wikimedia commons
#RSAC
What this means for you
20
Pitched battles and
cybersecurity are games
of wit.
Originality is your ace in
the hole.
#RSAC
Lesson #2: Be original
• ZeroDay philosophy
• Element of surprise
• Home field advantage
• Unique defense
• SEC vs. Pac-12
• Best players on defense
• Art of War chapter 13
• Collect evidence
• The “Moscow Rules”
• Muhammed Ali
#RSAC
Lesson #2: Be original
• What is malware?
• Characteristics, signatures, behavior
• Known vs. novel
• Analysis
• AV, sandboxing, white/blacklisting
• OK to reject safe programs
• Limitations
• Complexity, obfuscation, time
• Simplistic: malicious / non-malicious
• Education
• Awareness, policy, enforcement
#RSAC
Lesson 3: Know Thy Enemy
The Brilliant Statesmanship of Phillip II
#RSAC
Humble Beginnings, 359BC
24
#RSAC
Philip of Macedon
25
Historyofmacedonia.org Warner Brothers Pictures, 2004
#RSAC
Quadruple Threat
26
Dardanians
Paionians Thracians
Athenians
Noun Project credits:
Francielly Costantin Senra
Joshua McMahan
Creative Stall
Divya Kulshreshtha
#RSAC
Macedon from 359-338 BC
27
359BC 338BC
#RSAC
Lesson: know thy enemy
28
“If you know your enemies and
yourself, you will not be imperiled in a
hundred battles ... if you neither know
your enemies nor yourself, you will be
imperiled in every single battle.”
- Sun Tzu, The Art of War
#RSAC
Lesson #3: Know Thy Enemy
• 1980s: Cuckoo’s Egg
• 1990s: Moonlight Maze
• 1990s: Chechnya
• 1999: Kosovo
• 2007: Estonia
• 2008: Georgia
• 2009: Kyrgyzstan
• 2010: Microsoft
• 2011: Azerbaijan
• 2012: Red October
• 2013: Lithuania
• 2014: Ukraine
• 2015: Turkey
#RSAC
Lesson #3: Know Thy Enemy
• Analysis
• Data -> information -> intelligence
• Geopolitical insight
• Technical + non-technical
• Modelling
• Physics, analogies, napkins
• The “attribution” problem
• APT vs. APT
• Logic
• Think horses, then zebras
#RSAC
Lesson 4: Lead from the Front
The Conquests of Alexander the Great
#RSAC
Alexander the Great
32
Artcreationforver.com Warner Brothers Pictures, 2004
#RSAC
The Conquests of Alexander
33
334BC
323BC
#RSAC
Follow the Leader
34
• 334: Alexander crosses into Asia
• 334-332: Wins a streak of major victories
• Founds Alexandria in Egypt
• 331: Defeats Darius, king of the Persians
at the Battle of Gaugamela
• Enters Babylon
• Travels as far east as the Hindu Kush
and the Indus River
• 326: Troops beg Alexander to turn back
• Returns to Babylon via the Persian Gulf
• 323: Dies at age 32 Pbase.com
#RSAC
Follow the Leader
35
Wikipedia commons
#RSAC
Lesson #4: Lead from the Front
• Alexander the GEEK
• DIRNSA / CYBERCOM 2005-2014
• Education
• 4 Masters: EW, physics, strategy, business
• USMA ‘74: Petraeus (CIA), Dempsey (JCS)
• Dominant personality
• Like Hoover
• 10th Fleet, 24th Air Force, 2nd Army
• 40,000+ geek soldiers
• SIGINT today
• Proactive deterrence
• Massive mission expansion
• Cyber “fire support”
#RSAC
Lesson #4: Lead from the Front
• Cyber weapons
• Nukes of 21st century?
• Rated ahead of terrorism
• NSA / CYBERCOM
• Line blurring between traditional, digital
• Defend private sector?
• Alexander controversy
• Collection on US citizens
• US Congressman: “mockery of oversight”
• Militant on secrecy, leaks
• Iran counterattack post-Stuxnet
• Saudi Aramco, RasGas, Wall Street
• DHS: US energy should be on alert
#RSAC
Lesson 5: Fight Fire With Fire
Rome Reverse Engineers Carthage’s Tactics
#RSAC
Fast forward 100 years
39
#RSAC
Hannibal Barca
40
Ancienthistorylist.com
#RSAC
Act I: Elephants don’t belong in snow
41
The Punic Wars
• Carthage enters Spain,
Rome declares war under
false pretenses
• 218: Hannibal takes his
army, with elephants,
over the Alps & invades
Italy
• 216: Rome and Carthage
fight the Battle of Cannae
#RSAC
The Battle of Cannae, 218BC
42
“As the outer ranks fell, and the rest were gradually huddled in and surrounded, they were
all killed where they stood. While this murderous combat was going on, the Carthaginians
killed most of the cavalry and unseated others. Some 70,000 died bravely.”
- Polybius, The Histories
dcc.dickinson.edu
#RSAC
Scipio Africanus
43
Peoplecheck.deLeopard.booklikes.com
#RSAC
Act II: Return of the Romans
44
#RSAC
The Battle of Ilipa, 206BC
45
1: Crying wolf 3: The battle2: The wolf
Wikipedia commons
#RSAC
What this means for you
46
Don’t just know thy
enemy.
Act like them.
#RSAC
Lesson #5: Think like a hacker
• Cliff Stoll, SysAdmin vs. KGB (1986)
• Astronomer, inventor, physics teacher
• Followed $0.75 around the world
• Stoll gaffes
• Doubted e-commerce, e-media
• Pioneer in digital forensics
• Honeypot: “SDInet”
• Teleprinter recorded everything
• GNU Emacs vuln gave root access
• Capture of hacker Markus Hess
• Breached US military
#RSAC
Lesson #5: Think like a hacker
• What is this thing?
• How does it work?
• What else does it do?
• Is it secure?
• Can I break it?
• Can I improve it?
• Can I own it?
#RSAC
Conclusion: The Modern Perimeter
The Fall of the Roman Empire
#RSAC
Height of the Roman Empire: 200AD
50
#RSAC
Advance Persistent Threat: Barbarians
51
The Fall of Rome
• The borders are immense and
incredibly difficult to police
• Threats from the East & North
• When one army is in trouble,
others can’t come to their aid
• Political infighting divides the
empire – split in two
• Rome sacked twice
• Last Roman emperor killed in
476 Wikipedia commons
#RSAC
Parallel Lives
52
Classical
Greece
Phillip &
Alexander
Fragmentation The Rise
of Rome
The Fall
of Rome
Early
InfoSec
Dot Com
Era
InfoSec
Start-ups
InfoSec
Expands
Modern
Landscape
#RSAC
Drop us a line
53
zerofox.com
@zerofox
Spencer Wolfe
@wolfesp18
spencer@zerofox.com
Dr. Kenneth Geers
@kgeers
kgeers@zerofox.com

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Mash f03-five infosec-lessons_from_the_great_generals_of_the_ancient_world

  • 1. SESSION ID: #RSAC Kenneth Geers Five InfoSec Lessons from the Great Generals of the Ancient World MASH-F03 Ambassador NATO Cooperative Cyber Defence Centre of Excellence @kennethgeers Spencer Wolfe Head Security Research Writer ZeroFOX @wolfesp18
  • 2. #RSAC Introduction “The bravest among us are surely those who have the clearest vision of what is before them, danger and glory alike, and yet notwithstanding, go out to meet it.” -Thucydides, The History of the Peloponnesian War
  • 3. #RSAC What’s This Talk About, Again? 3 “Come then and let us pass a leisure hour in storytelling, and our stories shall become the education of our heroes.” --Plato, The Republic
  • 4. #RSAC Mappetizer 4 Phase 1: Greece Phase 2: Alexander the Great Phase 3: Roman Empire
  • 5. #RSAC Close Up: Greece 5 P E R S I A SPARTA ATHENS THEBES MACEDON
  • 6. #RSAC The History of Greece in a Single Slide ROME?? POWER YEAR (BC) Athenian Golden Age (Periclean Athens) Spartan Hegemony Battle of Salamis (479) Theban Hegemony Battle of Aegospotami (405) Battle of Leuctra (371) Battle of Chaeronea (338) Battle of Gaugamela (331) Conquests of Alexander the Great Persia = Athens = Sparta = Thebes = Macedon = Key Rise of Macedon
  • 7. #RSAC Lesson 1: Choose Your Battlefield Thermopylae, Salamis and the Greeks Fighting on Their Own Turf
  • 8. #RSAC Leonidas & Themistocles 8 Warner Brothers Pictures, 2006 Warner Brothers Pictures, 2014
  • 9. #RSAC The Greco-Persian Wars: 480-479 9 • Persia, under Xerxes, invades in Greece in 480 • Leonidas & the Spartans defend Thermopylae to the last man • In 479, the Persian navy is decisively defeated at Salamis by a Greek fleet led by Themistocles • Xerxes leaves, the rest of his army is destroyed at Plataea mapbox.com
  • 10. #RSAC Thermopylae: The Bottleneck 10 “The Persians were roughly handled by the Spartans, since they used shorter spears than the Greeks and could not use their numbers fighting in a narrow space. The Spartans fought memorably, showing themselves skilled fighters amidst unskilled.” -Herodotus, Histories (VII, 211) Brian Martens – 11/8/2012 livius.org
  • 11. #RSAC Salamis: Same Tactic, Different Element 11 “By engaging many ships with our few ships in the strait, we shall win a great victory. If the war turns out reasonably, it is to our advantage to fight in the strait and to their advantage to fight in the open ocean.” - Themistocles, from: Herodotus, Histories (VII, 60) www.arsbellica.it
  • 12. #RSAC Who cares? You do.POWER YEAR (BC) Battle of Salamis (479) Persia = Athens = Sparta = Thebes = KeyThings that might not have happened: • Democracy • Greek philosophy (Socrates, Plato, Aristotle) • Greek literature (The Iliad, The Odyssey) • Greek theater (Aeschylus, Sophocles, Euripides, Aristophanes) • Greek history (Herodotus, Thucydides, Xenophon) • Greek art • Greek medicine • The Rise of Rome • Christianity • Western Civilization….? Athenian Golden Age (Periclean Athens)
  • 13. #RSAC What this means for you 13 You know your system better than anyone, so… Where is your Thermopylae? Where is your Salamis? Where do you choose to fight?
  • 14. #RSAC Lesson #1: Choose your battlefield • Cyber terrain • USG: decrease # of nets, homogenize • Risk: all eggs in one basket • Utopia vs. Big Brother • Elections and surveillance • Belarus, China, Russia, Zimbabwe • Creativity on cyber defense • Code Red worm vs. MS IIS web server (2001) • Bot army: 359,000 infected servers • DoS Target: White House website • Techies “blackholed” the attack
  • 15. #RSAC Lesson #1: Choose your battlefield • Strategy before tactics • Crown jewels • Traffic analysis • Alice, Bob, Charlie • Old paradigm • Defined perimeter • New paradigm • Undefined perimeter, social media • Compartmentalization • Assume insider / penetration
  • 16. #RSAC Lesson 2: Be Original Epaminondas Beats the “Unbeatable” Spartans
  • 17. #RSAC Greece divided (again) 17 Greece after 479 • 479-431: Athenian Golden Age • 431-405: Peloponnesian War, fought between Athens and Sparta • Sparta defeats Athens • 405-371: Spartan Hegemony • 371: Thebes defeats Sparta at the Battle of Leuctra
  • 18. #RSAC The Greek Phalanx 18 • Rounds shields called hoplons • Overhand spear • Short sword called a xiphos • Shields overlap one another, forming a solid block • Opposing forces clash and try to push one another off the field • 8-12 men deep Ancientgreekbattles.net
  • 19. #RSAC Oblique Formation: Leuctra, 371BC 19 “The Spartans led each half-company three files abreast, and this resulted in the phalanx being not more than twelve men deep. The Thebans, however, were massed not less than fifty shields deep, calculating that if they conquered that part of the army around the king, all the rest of it would be easy to overcome.” - Xenophon, Hellenica Wikimedia commons
  • 20. #RSAC What this means for you 20 Pitched battles and cybersecurity are games of wit. Originality is your ace in the hole.
  • 21. #RSAC Lesson #2: Be original • ZeroDay philosophy • Element of surprise • Home field advantage • Unique defense • SEC vs. Pac-12 • Best players on defense • Art of War chapter 13 • Collect evidence • The “Moscow Rules” • Muhammed Ali
  • 22. #RSAC Lesson #2: Be original • What is malware? • Characteristics, signatures, behavior • Known vs. novel • Analysis • AV, sandboxing, white/blacklisting • OK to reject safe programs • Limitations • Complexity, obfuscation, time • Simplistic: malicious / non-malicious • Education • Awareness, policy, enforcement
  • 23. #RSAC Lesson 3: Know Thy Enemy The Brilliant Statesmanship of Phillip II
  • 25. #RSAC Philip of Macedon 25 Historyofmacedonia.org Warner Brothers Pictures, 2004
  • 26. #RSAC Quadruple Threat 26 Dardanians Paionians Thracians Athenians Noun Project credits: Francielly Costantin Senra Joshua McMahan Creative Stall Divya Kulshreshtha
  • 27. #RSAC Macedon from 359-338 BC 27 359BC 338BC
  • 28. #RSAC Lesson: know thy enemy 28 “If you know your enemies and yourself, you will not be imperiled in a hundred battles ... if you neither know your enemies nor yourself, you will be imperiled in every single battle.” - Sun Tzu, The Art of War
  • 29. #RSAC Lesson #3: Know Thy Enemy • 1980s: Cuckoo’s Egg • 1990s: Moonlight Maze • 1990s: Chechnya • 1999: Kosovo • 2007: Estonia • 2008: Georgia • 2009: Kyrgyzstan • 2010: Microsoft • 2011: Azerbaijan • 2012: Red October • 2013: Lithuania • 2014: Ukraine • 2015: Turkey
  • 30. #RSAC Lesson #3: Know Thy Enemy • Analysis • Data -> information -> intelligence • Geopolitical insight • Technical + non-technical • Modelling • Physics, analogies, napkins • The “attribution” problem • APT vs. APT • Logic • Think horses, then zebras
  • 31. #RSAC Lesson 4: Lead from the Front The Conquests of Alexander the Great
  • 32. #RSAC Alexander the Great 32 Artcreationforver.com Warner Brothers Pictures, 2004
  • 33. #RSAC The Conquests of Alexander 33 334BC 323BC
  • 34. #RSAC Follow the Leader 34 • 334: Alexander crosses into Asia • 334-332: Wins a streak of major victories • Founds Alexandria in Egypt • 331: Defeats Darius, king of the Persians at the Battle of Gaugamela • Enters Babylon • Travels as far east as the Hindu Kush and the Indus River • 326: Troops beg Alexander to turn back • Returns to Babylon via the Persian Gulf • 323: Dies at age 32 Pbase.com
  • 36. #RSAC Lesson #4: Lead from the Front • Alexander the GEEK • DIRNSA / CYBERCOM 2005-2014 • Education • 4 Masters: EW, physics, strategy, business • USMA ‘74: Petraeus (CIA), Dempsey (JCS) • Dominant personality • Like Hoover • 10th Fleet, 24th Air Force, 2nd Army • 40,000+ geek soldiers • SIGINT today • Proactive deterrence • Massive mission expansion • Cyber “fire support”
  • 37. #RSAC Lesson #4: Lead from the Front • Cyber weapons • Nukes of 21st century? • Rated ahead of terrorism • NSA / CYBERCOM • Line blurring between traditional, digital • Defend private sector? • Alexander controversy • Collection on US citizens • US Congressman: “mockery of oversight” • Militant on secrecy, leaks • Iran counterattack post-Stuxnet • Saudi Aramco, RasGas, Wall Street • DHS: US energy should be on alert
  • 38. #RSAC Lesson 5: Fight Fire With Fire Rome Reverse Engineers Carthage’s Tactics
  • 41. #RSAC Act I: Elephants don’t belong in snow 41 The Punic Wars • Carthage enters Spain, Rome declares war under false pretenses • 218: Hannibal takes his army, with elephants, over the Alps & invades Italy • 216: Rome and Carthage fight the Battle of Cannae
  • 42. #RSAC The Battle of Cannae, 218BC 42 “As the outer ranks fell, and the rest were gradually huddled in and surrounded, they were all killed where they stood. While this murderous combat was going on, the Carthaginians killed most of the cavalry and unseated others. Some 70,000 died bravely.” - Polybius, The Histories dcc.dickinson.edu
  • 44. #RSAC Act II: Return of the Romans 44
  • 45. #RSAC The Battle of Ilipa, 206BC 45 1: Crying wolf 3: The battle2: The wolf Wikipedia commons
  • 46. #RSAC What this means for you 46 Don’t just know thy enemy. Act like them.
  • 47. #RSAC Lesson #5: Think like a hacker • Cliff Stoll, SysAdmin vs. KGB (1986) • Astronomer, inventor, physics teacher • Followed $0.75 around the world • Stoll gaffes • Doubted e-commerce, e-media • Pioneer in digital forensics • Honeypot: “SDInet” • Teleprinter recorded everything • GNU Emacs vuln gave root access • Capture of hacker Markus Hess • Breached US military
  • 48. #RSAC Lesson #5: Think like a hacker • What is this thing? • How does it work? • What else does it do? • Is it secure? • Can I break it? • Can I improve it? • Can I own it?
  • 49. #RSAC Conclusion: The Modern Perimeter The Fall of the Roman Empire
  • 50. #RSAC Height of the Roman Empire: 200AD 50
  • 51. #RSAC Advance Persistent Threat: Barbarians 51 The Fall of Rome • The borders are immense and incredibly difficult to police • Threats from the East & North • When one army is in trouble, others can’t come to their aid • Political infighting divides the empire – split in two • Rome sacked twice • Last Roman emperor killed in 476 Wikipedia commons
  • 52. #RSAC Parallel Lives 52 Classical Greece Phillip & Alexander Fragmentation The Rise of Rome The Fall of Rome Early InfoSec Dot Com Era InfoSec Start-ups InfoSec Expands Modern Landscape
  • 53. #RSAC Drop us a line 53 zerofox.com @zerofox Spencer Wolfe @wolfesp18 spencer@zerofox.com Dr. Kenneth Geers @kgeers kgeers@zerofox.com