Jessica	DeVita
Technical	Evangelist
Chef	Software
@ubergeekgirl
Baking Safety Into
Infrastructure Testing
What the heck is an
evangelist?
Baking Safety into Infrastructure Testing
Baking Safety into Infrastructure Testing
Baking Safety into Infrastructure Testing
• Software
• Safety
• Common ground
• Compliance as code
Software is everywhere!
Motorcycles
Baking Safety into Infrastructure Testing
Medical Devices
Pre-DevOps
DevOps to the rescue!
Baking Safety into Infrastructure Testing
Why does safety matter?
Baking Safety into Infrastructure Testing
What about Security?
Dev
QA
Security	Review
Staging
Prod
Patching
I love	working	with	our	security	team,	
Said	no one	ever
Regulations!
OFAC USA	PATRIOT	Act Gramm-Leach-Bliley	Act Red	Flags	Rule
Bank	Secrecy	Act Sarbanes-Oxley Regulation	E Dodd-Frank
False	Claims	Act HIPAA
European	Central	Bank	
regulations
Prudential	Regulation	
Authority
Financial	Conduct	
Authority
HITECH PCI	DSS
Baking Safety into Infrastructure Testing
Baking Safety into Infrastructure Testing
"Society's ability to regulate industries
effectively is limited by it's ability to access
and understand code, as we saw with the
VW emissions scandal." @richardjpope
Fear-based culture
Baking Safety into Infrastructure Testing
Baking Safety into Infrastructure Testing
Safety can be predicted by
organizational culture
RonWestrum
Psychological Safety is the most powerful
predictor of successful teams
John
Allspaw
PDF Club
Common Ground
and Coordination
in Joint Activity
Intention
• Phases
• Signaling
• Coordination
devices &
costs
• Interpredictability
• Common Ground
• Directability
Common	Ground	in	Joint	Activity
• Intention
• Signals	and	cues
• Conversation,	effective	Coordination
• Inter-predictability
• Common	Ground
• Who	knows	what
• Taskwork vs.	teamwork
• Joint	action	ladder
Intention
Interdependence
Common ground is
Not a "thing"
Not a state
Instead, it is a process
an ongoing action: grounding
http://www.stefanomastrogiacomo.info/wp-content/uploads/2012/11/Common-Ground.png
Choreography
Choreography
Communication
proceeds on
two tracks:
Task
Work
Team
Work
Signaling
Signaling carries a responsibility
to judge the interrupt-ability of
the other person
http://corgibytes.com/blog/2016/04/15/inception-layers/
ChatOps?
All communication
is done through the board
Coordination: managing dependencies
between activities
Coordination cannot be
manufactured through procedures
and explicit guidelines.
Common Ground is Not:
everyone having the same knowledge
Baking Safety into Infrastructure Testing
Interpredictability
Common Ground
Pertinent Mutual Knowledge,
Beliefs, and Assumptions
roles and functions
routines
skills and competencies
goals and commitment
stance:
perceptions of time pressure
fatigue
competing priorities
Most important types:
Pertinent Mutual Knowledge,
Beliefs, and Assumptions
common ground is created or
lost during handoffs.
https://www.flickr.com/photos/53370644@N06/4976497160
Why	do	teams	lose	common	
ground?
• No experience working together
• Access to different data
• No clear rationale for the directives
• Ignorance of different stances
• Unexpected loss of communications and unskilled
at repairing the disruption
• Failure to monitor confirmation of messages
• Confusion over who knows what – fundamental
common ground breakdown
3.	Understand
Understanding
Acting
The Joint Action Ladder
4.	Act
2.	Perceive
1.	Attend
Fundamental Common
Ground Breakdown:
Common ground is not binary!
Teams engage in activities to support common
ground
• structuring preparations(establish routines)
• sustaining (clarifications, reminders)
• updating others about changes
• monitoring other team members
• detecting (anomalies, signals of loss of ground)
repairing the loss
"No matter how much care is taken,
breakdowns in common ground are
inevitable. No amount of procedure
or documentation can totally
prevent them."
High reliability organizations are marked by a
continual mindfulness, a continual searching for
indications of a loss of common ground
Safety	is	conveyed	through	actions
• actions	can	be	code
• actions	can	be	conversations
Making automation a team player
https://tctechcrunch2011.files.wordpress.com/2015/06/robotdap-e1433960740130.jpg
Baking Safety into Infrastructure Testing
InSpec is compliance as code – a
human-readable language for
automating the continuous testing and
compliance auditing of your entire
infrastructure.
SSH	Control
SSH	supports	two	different	protocol	
versions.	The	original	version,	SSHv1,	
was	subject	to	a	number	of	security	
issues.	Please	use	SSHv2	instead	to	
avoid	these.
Mapping	Compliance	to	InSpec
control 'ssh-6.2.1' do
title 'Set SSH Protocol to 2'
end
Mapping	Compliance	to	InSpec
control 'ssh-6.2.1' do
title 'Set SSH Protocol to 2'
desc "
SSH supports two different ...
"
end
Mapping	Compliance	to	InSpec
control 'ssh-6.2.1' do
title 'Set SSH Protocol to 2'
desc "
SSH supports two different ...
"
describe sshd_config do
its('Protocol') { should cmp('2')
}
end
end
Mapping	Compliance	to	InSpec
control 'ssh-6.2.1' do
impact 1.0
title 'Set SSH Protocol to 2'
desc "
SSH supports two different ...
"
describe sshd_config do
its('Protocol') { should cmp('2')
}
end
end
Test Any Target
inspec exec test.rb
inspec exec test.rb -i ~/.aws/mandi_eu.pem -t ssh://ec2-
user@54.152.7.203
inspec exec test.rb -t winrm://Admin@192.168.1.2 --password
super
inspec exec test.rb -t docker://3dda08e75838
its.... should...
•it { should exist }
•it { should be_installed }
•it { should be_enabled }
•its('max_log_file') { should cmp 6 }
•its('exit_status') { should eq 0 }
•its('gid') { should eq 0 }
InSpec Profiles
include_controls 'os-hardening' do
skip_control 'os-06'
control 'os-02' do
impact 0.7
end
end
include_controls 'ssh-hardening'
describe security_policy do
its('PasswordComplexity') { should eq 1 }
end
describe sshd_config do
its('Port') { should eq('22') }
End
describe iis_site('Default Web Site') do
it { should
have_app_pool('DefaultAppPool') }
it { should have_binding('http *:80:') }
end
67
Baking Safety into Infrastructure Testing
Baking Safety into Infrastructure Testing
Baking Safety into Infrastructure Testing
Truth can only be
found in one place:
the code.
Only the code can
truly tell you what it
does. It is the only
source of truly
accurate
information.
jessica@chef.io
@UberGeekGirl

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Baking Safety into Infrastructure Testing