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Alison Gianotto
@snipeyhead
SECURITY BOOTCAMP
FOR STARTUPS(and Small Businesses)
Alison Gianotto (aka “snipe”)
WHO AM I?
•Former	agency	CTO/CSO	
•CTO	of	Anysha.re	
•Creator	of	Snipe-IT	FOSS	project	
•Security	&	privacy	advocate	
•20	years	in	IT	and	software	dev	
•Co-author	of	a	few	PHP/MySQL	books	
•@snipeyhead	on	Twitter
2DomCode	2016	-	Utrecht	-	#DomCode16
3
WHAT IS RISK?
4DomCode	2016	-	Utrecht	-	#DomCode16
Risk is the combination of
threat, vulnerability, and
mission impact.
WHAT KINDS OF THREATS?
5DomCode	2016	-	Utrecht	-	#DomCode16
•Not	always	hackers	
•Physical	threats:	natural	disasters,	such	as	flood,	
fire,	earthquakes,	etc	
•Logical	threats:	bugs	in	hardware,	power	failures	
•Human	threats:	non-malicious	and	malicious	
threats,	such	as	disgruntled	employees	and	
hackers
RISK TOLERANCE
6DomCode	2016	-	Utrecht	-	#DomCode16
If vulnerability is high, but
mission impact is low, you
can probably tolerate that
risk.
ONE SIZE DOES NOT FIT ALL
7DomCode	2016	-	Utrecht	-	#DomCode16
Risk looks different for each
organization.
IT IS IMPOSSIBLE TO
ANTICIPATE OR MITIGATE
EVERY RISK.
8DomCode	2016	-	Utrecht	-	#DomCode16
WHY SHOULD YOU CARE?
9DomCode	2016	-	Utrecht	-	#DomCode16
Security breaches cost a
company reputation,
money, time & trust.
WHY SHOULD YOU CARE?
10DomCode	2016	-	Utrecht	-	#DomCode16
Identity theft and security
vulnerabilities affect the
lives of real people - your
users.
WHY SHOULD YOU CARE?
11DomCode	2016	-	Utrecht	-	#DomCode16
Source:	Forbes	Magazine,	Aug	3,	2013
WHY SHOULD YOU CARE?
12DomCode	2016	-	Utrecht	-	#DomCode16
Source:	BoingBoing	-	Nov	3,	2016
WHY SHOULD YOU CARE?
13DomCode	2016	-	Utrecht	-	#DomCode16
Even if your product can’t
be weaponized, the data you
store and the trust your
users have in you can be.
14DomCode	2016	-	Utrecht	-	#DomCode16
GDPR
•Goes	into	effect	2018	
•Could	result	in	fines	of	€20m	or	4%	of	your	
annual	turnover,	whichever	is	GREATER
(General Data Protection Regulation)
In 2013, 61% of reported
attacks targeted small and
medium businesses, UP
from 50% in 2012.
15DomCode	2016	-	Utrecht	-	#DomCode16
Source:	Verizon	Communications	2013	Data	Breach	Investigations	Report
One study found that
compromises of mid-size
firms rose 64% from 2013
to 2014.
16DomCode	2016	-	Utrecht	-	#DomCode16
Source:	Global	State	of	Information	Security	Survey	2015
HOW?
17DomCode	2016	-	Utrecht	-	#DomCode16
Sometimes an attacker will
use your product to gain
information, sometimes
they’ll use YOU.
HOW?
18DomCode	2016	-	Utrecht	-	#DomCode16
And sometimes your users
are the target, and
sometimes your company is.
WAYS THEY USE YOUR PRODUCT
19DomCode	2016	-	Utrecht	-	#DomCode16
•Reflected	XSS	
•Persistent	XSS	
•CSRF	
•SQL	Injection	
•Remote	file	inclusion		
•Local	file	inclusion/
directory	traversal	
•Defacement	for	SEO	
(pharma,	etc)	
•Privilege	escalation	
•Malware	delivery	
•Other	stuff	you	know	
from	OWASP
WAYS THEY USE YOU
20DomCode	2016	-	Utrecht	-	#DomCode16
•Stealing	credentials	from	other	websites,	hoping	
you	re-use	passwords	across	sensitive	systems	
•Spear-phishing	
•Watering	hole	attacks	
•Social	engineering	
•Malware	
•Insecure	third-party	vendors
DEFENSE IN DEPTH
21DomCode	2016	-	Utrecht	-	#DomCode16
•Mitigates	single	points	of	failure.	(“Bus	factor”)	
•Requires	more	effort	on	the	part	of	the	
attacker,	theoretically	exhausting	attacker	
resources.	
Except...
DEFENSE IN DEPTH CHALLENGES
22DomCode	2016	-	Utrecht	-	#DomCode16
•Larger,	more	complicated	systems	can	be	harder	to	
maintain:	
•Leads	to	more	cracks	for	bad	guys	to	poke	at	
•More	surfaces	that	can	get	be	overlooked		
•The	bad	guys	have	nearly	limitless	resources.	We	don’t.		
•Attacks	are	commoditized	now.		Botnets	for	<	$2/hour	
and	Internet	of	Shit	(Mirai	DynDNS	attack)
CIA
Confidentiality,
Integrity &
Availability
CONFIDENTIALITY IS A SET OF
RULES THAT LIMITS ACCESS TO
INFORMATION
24DomCode	2016	-	Utrecht	-	#DomCode16
CONFIDENTIALITY EXAMPLES
25DomCode	2016	-	Utrecht	-	#DomCode16
•Passwords	
•Data	encryption	(at	rest	
and	in	transmission)	
•Two-factor	
authentication	or	
biometrics.	
•Corporate	VPN	
•IP	Whitelisting	
•SSH	keys
CONFIDENTIALITY RISKS
26DomCode	2016	-	Utrecht	-	#DomCode16
• No	brute-force	detection	
• No	vetting	of	how	third-
party	vendors	use/store	
customer	data	
• Information	leakage	from	
login	messages	(timing	
attacks,	etc.)	
• SQL	injection		
• Privilege	escalation	leading	
to	admin	access		
• Passwords	shared	across	
websites	
• Improper	disposal/
destruction	of	personal	
data	
• Lost/stolen	devices	
• Insider	Threats
INTEGRITY IS THE ASSURANCE
THAT THE INFORMATION IS
TRUSTWORTHY & ACCURATE.
27DomCode	2016	-	Utrecht	-	#DomCode16
INTEGRITY RISKS
28DomCode	2016	-	Utrecht	-	#DomCode16
• Data	loss	due	to	hardware	
failure	(server	crash!)	
• Software	bug	that	
unintentionally	deletes/
modifies	data	
• Data	alteration	via	
authorized	persons	(human	
error)	
•Data	alteration	via	
unauthorized	persons	
(hackers)	
•No	backups	or	no	way	to	
verify	the	integrity	of	the	
backups	you	have	
•Third-party	vendor	with	
inadequate	security	
•Insider	Threats
AVAILABILITY IS A GUARANTEE OF
READY ACCESS TO THE INFO BY
AUTHORIZED PEOPLE.
29DomCode	2016	-	Utrecht	-	#DomCode16
AVAILABILITY RISKS
30DomCode	2016	-	Utrecht	-	#DomCode16
•DDoS	attacks	
•Third-party	service	
failures	
•Hardware	failures	
•Software	bugs	
•Untested	software	
patches	
•Natural	disasters	
•Man-made	disasters	
•Insider	Threats
Hmm… This
looks familiar…
31DomCode	2016	-	Utrecht	-	#DomCode16
INSIDER THREATS
42%
58%
• Employees	(33%)	
• Ex-employees	(7%)		
• Customers,	partners	or	
suppliers	(18%)
Source:	Clearswift	Report:	The	Enemy	Within	-	Published	May	2013
• Everything	else
32DomCode	2016	-	Utrecht	-	#DomCode16
INSIDER THREATS
Source:	Clearswift	Report:	The	Enemy	Within	-	Published	May	2013
•Often	very	low-tech	
•Sometimes	malicious	
•Sometimes	accidental	
•Theft/destruction	of	
confidential	
information	
•Sabotage		
•Fraud	
•Defacement	
•DoS	attacks	
•Sometimes	motivated	
by	revenge
NOT ALL INSIDER THREATS ARE
MALICIOUS, BUT THAT DOESN’T
MAKE THEM LESS DANGEROUS.
33DomCode	2016	-	Utrecht	-	#DomCode16
34DomCode	2016	-	Utrecht	-	#DomCode16
APPLICATION SECURITY
77% OF LEGITIMATE WEBSITES HAD
EXPLOITABLE VULNERABILITIES.
1-IN-8 HAD A CRITICAL
VULNERABILITY.
35DomCode	2016	-	Utrecht	-	#DomCode16
Source:	Symantec	Internet	Security	Threat	Report	2014	::	Volume	19,	Published	April	2014
BREACHGrowth • credit card info
• birth dates
• gov ID numbers
• home addresses
• medical records
• phone numbers
• financial information
• email addresses
• login
• passwords
Data Stolen
36DomCode	2016	-	Utrecht	-	#DomCode16
Iden**es	Stolen	by	Year	(in	Millions)
275
550
825
1100
2011 2012 2013 2014 2015 2016*
554
707
1,023
552
267
412
Source:	Symantec	Internet	Security	Threat	Report	2014		/	2015
2011 2012 2013 2014 2016
974,000
500,000
570,000
464,000
190,000
ATTACKS
37
Source:	Symantec	Internet	Security	Threat	Report	2014/2016
Per Day
DomCode	2016	-	Utrecht	-	#DomCode16
APPSEC STRATEGY
PICK	TWO
38
COMPLETELY	SCREWEDCOMPLETELY	SCREWED
COMPLETELY	SCREWED
DomCode	2016	-	Utrecht	-	#DomCode16
39DomCode	2016	-	Utrecht	-	#DomCode16
WHAT CAN YOU DO?
STOP:
40DomCode	2016	-	Utrecht	-	#DomCode16
Believing the lie that you’re
too small to be a target.
You’re not. I promise.
START:
41DomCode	2016	-	Utrecht	-	#DomCode16
Evaluating the value of your
assets. You have to know
what you’re protecting.
42DomCode	2016	-	Utrecht	-	#DomCode16
VENDOR MANAGEMENT
START:
43DomCode	2016	-	Utrecht	-	#DomCode16
Documenting ALL of your
third-party vendors. Assess
risk, and start a vendor
management program.
START:
44DomCode	2016	-	Utrecht	-	#DomCode16
Giving preference to third-
party vendors that
integrate with LDAP/AD/
SSO.
START:
45DomCode	2016	-	Utrecht	-	#DomCode16
Developing a risk matrix for
every project. Keep it
updated as new features are
added.
RISK MATRIX:
46DomCode	2016	-	Utrecht	-	#DomCode16
• Type	
• Third-Party	
• Service	Description	
• Triggering	Action	
• Consequence	of	Service	
Failure	
• Risk	of	Failure	
• Probability	of	Failure	
• User	Impact	of	Failure	
• Method	used	for	monitoring	
this	risk	
• Efforts	to	Mitigate	in	Case	of	
Failure	
• Contact	info
Grab	a	starter	template	here!		
http://snipe.ly/risk_matrix
START:
47DomCode	2016	-	Utrecht	-	#DomCode16
Giving preference to systems
that allow you to show due
diligence in the event of a
breach.
48DomCode	2016	-	Utrecht	-	#DomCode16
POLICIES & PROCESS
START:
49DomCode	2016	-	Utrecht	-	#DomCode16
Implementing policies of
“least-privilege”.
START:
50DomCode	2016	-	Utrecht	-	#DomCode16
Developing a Disaster
Recovery Plan. TEST IT. (No,
really, test it. Often.)
START:
51DomCode	2016	-	Utrecht	-	#DomCode16
Developing an Incident
Response Plan. Test it, and
keep it updated.
START:
52DomCode	2016	-	Utrecht	-	#DomCode16
Enabling (and requiring)
two-factor authentication
for everything.
START:
53DomCode	2016	-	Utrecht	-	#DomCode16
Thinking about any ways a
new security measure could
actually weaken your
security.
REMEMBER:
54DomCode	2016	-	Utrecht	-	#DomCode16
If your new security policies
get in the way of people
getting work done, they will
find a way around them.
START:
55DomCode	2016	-	Utrecht	-	#DomCode16
Developing a formal
procedure for handling
exiting employees.
56DomCode	2016	-	Utrecht	-	#DomCode16
DATA HANDLING
STOP:
57DomCode	2016	-	Utrecht	-	#DomCode16
Collecting data about users
that you don’t
ABSOLUTELY need right
now.
START:
58DomCode	2016	-	Utrecht	-	#DomCode16
Logging (almost) everything.
Use a central logging server
if you can.
START:
59DomCode	2016	-	Utrecht	-	#DomCode16
Getting to know what
“normal” user behavior
looks like. Flag anything out
of the ordinary.
START:
60DomCode	2016	-	Utrecht	-	#DomCode16
Storing offline backups.
Make sure you can restore
from them successfully.
START:
61DomCode	2016	-	Utrecht	-	#DomCode16
Encrypting EVERYTHING
(where feasible.) in transit
and at rest.
HTTPS ALL THE THINGS.
START:
62DomCode	2016	-	Utrecht	-	#DomCode16
Testing that your
deployment system can
work if Github (or other
third-party) is down.
63DomCode	2016	-	Utrecht	-	#DomCode16
DEV & OPS
START:
64DomCode	2016	-	Utrecht	-	#DomCode16
Leveraging the built-in data
sanitation/CSRF of your
language frameworks.
START:
65DomCode	2016	-	Utrecht	-	#DomCode16
Using prepared statements
for your SQL. It’s 2016
already!
START:
66DomCode	2016	-	Utrecht	-	#DomCode16
Checking for debugging
output that can disclose
information that can make
an attacker’s job easier.
STOP:
67DomCode	2016	-	Utrecht	-	#DomCode16
Using MD5 for passwords!!!!
Use a secure salt+hash like
bcrypt.
START:
68DomCode	2016	-	Utrecht	-	#DomCode16
Looking critically at the
complexity of your systems.
START:
69DomCode	2016	-	Utrecht	-	#DomCode16
Implementing brute-force
detection everywhere you
can.
STOP:
70DomCode	2016	-	Utrecht	-	#DomCode16
Using production data in
your test environments!
START:
71DomCode	2016	-	Utrecht	-	#DomCode16
Getting your dev teams
involved in Capture the Flag
events. (They’re fun!)
START:
72DomCode	2016	-	Utrecht	-	#DomCode16
Getting penetration tests
and vulnerability
assessments done.
START:
73DomCode	2016	-	Utrecht	-	#DomCode16
Building automated
scanners into your testing/
Continuous Integration
pipeline.
74DomCode	2016	-	Utrecht	-	#DomCode16
COMPANY CULTURE
START:
75DomCode	2016	-	Utrecht	-	#DomCode16
Building a security-first
culture. Make it part of your
DNA.
START:
76DomCode	2016	-	Utrecht	-	#DomCode16
Creating a company culture
where your employees are
encouraged to ask if they
are suspicious.
REMEMBER:
77DomCode	2016	-	Utrecht	-	#DomCode16
“The security team says no because
they are incorrectly held accountable
for all flaws.”
— Michael Coates
CISO at Twitter, OWASP Global Board Member
START:
78DomCode	2016	-	Utrecht	-	#DomCode16
Educating employees about
social engineering tactics
that can be used to gather
data about your company.
STOP:
79DomCode	2016	-	Utrecht	-	#DomCode16
Utilizing policies that punish
employees for reporting
incidents.
START:
80DomCode	2016	-	Utrecht	-	#DomCode16
Becoming a passionate
security ambassador for
your users and your co-
workers.
Alison Gianotto (aka “snipe”)
THANK YOU!
• @snipeyhead	on	Twitter	
• snipe@snipe.net
81DomCode	2016	-	Utrecht	-	#DomCode16
Liked	this	talk?	Leave	feedback	at		
http://snipe.ly/domcode16
CAPTURE ALL THE FLAGS!
82DomCode	2016	-	Utrecht	-	#DomCode16
• NotSoSecure	CTF:	http://ctf.notsosecure.com	
• Security	Shepherd:	https://www.owasp.org/index.php/OWASP_Security_Shepherd	
• http://hax.tor.hu/	
• https://pwn0.com/	
• http://www.smashthestack.org/	
• http://www.hellboundhackers.org/	
• http://www.overthewire.org/wargames/	
• http://counterhack.net/Counter_Hack/Challenges.html	
• http://www.hackthissite.org/	
• http://exploit-exercises.com/	
• http://vulnhub.com/

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