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LONDON 18-19 OCT 2018
Mike Shema
@CodexWebSecurum
Building Effective DevSecOps

Teams Through Role-Playing Games
The Masquerade: Second Edition. White Wolf Game Studio. 1997.
Monstrously Manual
As we treat infrastructure as code and
make code more human-readable, we
must still find ways to read humans.
DevOps
Automation
Required to scale.
Establishes consistency.
Enables confident iteration.
Dev[Sec]Ops
People
Working with them.
Working for them.
Building for them.
Actual Problem Ignored
Users are stupid.
Devs are lazy.
Vuln equals risk.
https://www.usenix.org/legacy/publications/library/proceedings/sec99/whitten.html
Fantasy Campaign Setting
User Intelligence -2; Wisdom -2
Developer Intelligence -2; Wisdom -2
Collaborative
story-telling
Shared goals
Communication
exercises
Barbarian

Fighter

Magic-User

Thief

Cleric

Ranger

Bard
Coder, Sysadmin

DevOps

DevOps at scale

Red Team

Blue Team

Threat Hunting

CISO
The Masquerade: Second Edition. White Wolf Game Studio. 1997.
Communication
Empathy
Threats
Shared
Vocabulary
Communication
Listen
Acknowledge
Repeat back
Empathy
Broaden understanding
Reconsider viewpoints
Improve solutions
Constructive feedback
Threats
Ambiguity
Blame
Erasure
Essentializing
Codes of Conduct
Set expectations, standards of behavior.
Describe a path for conflict resolution,
define consequences.
Foster participation.
Example: https://golang.org/conduct
https://captainawkward.com
RPG
Threat
Models
Roll for initiative.
Split the party.
Touch the statue.
Attack the darkness.
A Fiendish Folio
Abuse, directed or distributed
Asymmetric costs of effort or attention
Forced participation
Security as a cost
Privacy*
*Summons 2d6 more privacy demons
…and more fiends
Asymmetric features
Unexpected design
AR and VR vectors
DevTruSafOps
Ratings without context or with irrelevant
context.
Reputational damage. Reputational abuse.
Involuntary participation, added to list of X,
added to repo of Y.
DevPrivOps
Metadata leaks
De-anonymization
of identity
De-aggregation of
cohorts
Privacy by
Design
Coarseness of data.
Storage of data.
Use of data.
Protocols &

Ceremonies
Ceremonies
How are users included in the system?
How are they modeled, what is expected
of them?
Do they have the tools, knowledge, skills
to accomplish what’s expected?
https://eprint.iacr.org/2007/399.pdf
Attacking the Darkness
Ambiguity in design, omitting the user.
Assuming a uniform user.
Not perceiving a user’s threat model.
Not measuring a ceremony’s effectiveness.
Metrics: The Observation
Build a Story (Cautiously)
Ask an interesting & relevant question.
Collect signals, beware silence.
Create metrics, beware tunnel vision.
Create a story, beware myth.
50% of Findings
Threats
Lack of signals
Unrepresentative signals
Tunnel vision
Information bias & many more cognitive
biases
https://www.businessinsider.com/cognitive-biases-affect-decisions-2015-8/
Unearthing Arcana
What we measure also reflects what we
care about.
What we care about also reflects on our
environment.
Mind Flayer
RPGs continue to evolve.
Cliques, in-groups, and gate-
keeping are threats to any
social group.
Not everyone is familiar with
RPGs.
Tabletop Exercises
Scenario
Objectives
Participants
Rules & Scope
Referee
Reduces stress
Enables learning
Practices ceremonies
Generates feedback
The CTO directs a DevOps team member to
improve analytics. They export a production
DB into a 3rd-party business intelligence tool
for a proof-of-concept.

They grant access to every team member.
The data includes password hashes.
Create relevant scenarios.
Attack the objective, not
the scenario.
Review feedback on
people, process, & tools.
Review feedback on rules
& rulings.
RPG Interpersonal Skills
Compromise
Negotiation
Patience
Team-building
Made by people
Made for people
Made of people
Soylent
Soylent
Soylent
@CodexWebSecurum
Appendix N
https://www.usenix.org/legacy/publications/library/proceedings/sec99/
whitten.html
https://eprint.iacr.org/2007/399.pdf
https://captainawkward.com
https://www.crashoverridenetwork.com
https://geekfeminism.wikia.com/wiki/Category:Concepts
https://tallpoppy.io
https://businessinsider.com/cognitive-biases-affect-decisions-2015-8/
https://www.contributor-covenant.org/version/1/4/code-of-conduct
–Tron, TRON
“I don't wanna bust out of here
and find nothing but a lot of
cold circuits waiting for me.”
LONDON 18-19 OCT 2018
end of line.

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