Technology Security Through Absurdity: Lessons Learned

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Dyn Director of Security Chris Brenton did a presentation in NYC regarding DNS security and how he learned some valuable lessons the absurd way.

Transcript of Technology Security Through Absurdity: Lessons Learned

Security Through Absurdity:

Lessons Learned

December 13th, 2013

Security Through Absurdity:

Lessons Learned

December 13th, 2013

Chris Brenton

Director of Security

@chris_brenton

cbrenton@dyn.com

Why Security Through Absurdity?

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Because we need to enjoy life’shumorous moments

Two paths lie before you…

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Enjoy the Journey

•Find the humor “nuggets”•Leverage the life lessons•Grow and move forward

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•Find the humor “nuggets”•Leverage the life lessons•Grow and move forward

Let It Thin Your Soul

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“Like butter scraped overtoo much bread”

Rock The Gandalf Look

By increasing the gray hair density

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By increasing the gray hair density

Rock The Gandalf Look

By increasing the gray hair density

I already have a 14 yr old daughter

dedicated to that last task

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By increasing the gray hair density

I already have a 14 yr old daughter

dedicated to that last task

Our Journey Begins

Contracted as a security consultant

Owner wants locked down VPN

access to business

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Contracted as a security consultant

Owner wants locked down VPN

access to business

Security Requirements

Normally disabled state

Must call first to get access

Must know IP address

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Normally disabled state

Must call first to get access

Must know IP address

More Security Requirements

2 Factor authentication

Time limit on access

Log and alert on everything!

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2 Factor authentication

Time limit on access

Log and alert on everything!

First Day Onsite

I show up early

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First Day Onsite

I show up early

UPS arrives

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I show up early

UPS arrives

First Day Onsite

I show up early

UPS arrives

Retrieves key from under rock

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I show up early

UPS arrives

Retrieves key from under rock

First Day Onsite

I show up early

UPS arrives

Retrieves key from under rock

Lets themselves into building

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I show up early

UPS arrives

Retrieves key from under rock

Lets themselves into building

Is This A Problem?

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Is This A Problem?

Key has been under rock for 5 years

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Is This A Problem?

Key has been under rock for 5 years

Everyone knows its there

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Key has been under rock for 5 years

Everyone knows its there

Is This A Problem?

Key has been under rock for 5 years

Everyone knows its there– “X” employees (including disgruntle ones)– All delivery couriers

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Key has been under rock for 5 years

Everyone knows its there– “X” employees (including disgruntle ones)– All delivery couriers

Is This A Problem?

Key has been under rock for 5 years

Everyone knows its there– “X” employees (including disgruntle ones)– All delivery couriers– Even the local pizza parlor staff

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Key has been under rock for 5 years

Everyone knows its there– “X” employees (including disgruntle ones)– All delivery couriers– Even the local pizza parlor staff

Did I Forget to Mention…

Business model was computer sales

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Did I Forget to Mention…

Business model was computer sales

In excess of $15K in inventory

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Business model was computer sales

In excess of $15K in inventory

Did I Forget to Mention…

Business model was computer sales

In excess of $15K in inventory

Nothing high risk saved on the

corporate network

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Business model was computer sales

In excess of $15K in inventory

Nothing high risk saved on the

corporate network

Security Task List

Mitigate risks that could put you out

of business next week

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Mitigate risks that could put you out

of business next week

Security Task List

Mitigate risks that could put you out

of business next week

Then move on to the week after that

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Mitigate risks that could put you out

of business next week

Then move on to the week after that

Security Task List

Mitigate risks that could put you out

of business next week

Then move on to the week after that

Lather, rinse repeat

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Mitigate risks that could put you out

of business next week

Then move on to the week after that

Lather, rinse repeat

What Did Life Teach Me?

Never assume a business risk analysis

has been performed

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Never assume a business risk analysis

has been performed

What I Now Do Differently

Don’t assume your contact

understands their risks

Perform a mini risk assessmentPg. 28 Security Through Absurdity: Lessons Learned @chris_brenton

Don’t assume your contact

understands their risks

Perform a mini risk assessment

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We implemented a great security solution…But don’t have resources to maintaining it

Case Study #2

Phishing test

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Phishing test

Phishing Test Exercise

Contracted to help IT test

social engineering

Test all employees via email

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Contracted to help IT test

social engineering

Test all employees via email

The Setup

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The Results

13 of 450 employees hit reply

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The Results

13 of 450 employees hit reply

Sent their logon credentials

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13 of 450 employees hit reply

Sent their logon credentials

The Results

13 of 450 employees hit reply

Sent their logon credentials

Via plaintext email

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13 of 450 employees hit reply

Sent their logon credentials

Via plaintext email

The Results

13 of 450 employees hit reply

Sent their logon credentials

Via plaintext email

To an unknown outside address

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13 of 450 employees hit reply

Sent their logon credentials

Via plaintext email

To an unknown outside address

The Response

Email sent from real IT account

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The Response

Email sent from real IT account

Phishing test revealed

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Email sent from real IT account

Phishing test revealed

The Response

Email sent from real IT account

Phishing test revealed

Detailed explanation

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Email sent from real IT account

Phishing test revealed

Detailed explanation

The Response

Email sent from real IT account

Phishing test revealed

Detailed explanation

Phishing email included as reference

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Email sent from real IT account

Phishing test revealed

Detailed explanation

Phishing email included as reference

What Happened Next?

19 people hit “reply”

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What Happened Next?

19 people hit “reply”

and sent their credentials

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19 people hit “reply”

and sent their credentials

What Happened Next?

19 people hit “reply”

and sent their credentials

In response to an email telling

them never to do this

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19 people hit “reply”

and sent their credentials

In response to an email telling

them never to do this

Math Sanity Check…

13 < 19

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Root Cause Analysis

“I just skipped to the executive

summary”

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“I just skipped to the executive

summary”

What Did Life Teach Me?

Email is the wrong medium for

in-depth concepts

How you convey info matters

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Email is the wrong medium for

in-depth concepts

How you convey info matters

What I Now Do Differently

Consider the proper medium to

convey required information

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Consider the proper medium to

convey required information

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We rely on host-based security… To warn uswhen the host has been compromised

Case Study #3

Phishing Rev 2

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Phishing Rev 2

Phishing Attack

Spoofed email from CEO

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Phishing Attack

Spoofed email from CEO

Claims to point to a BBC article

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Spoofed email from CEO

Claims to point to a BBC article

Phishing Attack

Spoofed email from CEO

Claims to point to a BBC article

Link prompts for email logon

name and password

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Spoofed email from CEO

Claims to point to a BBC article

Link prompts for email logon

name and password

The Results

6 people are duped

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The Results

6 people are duped

Give away their logon name

and password

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6 people are duped

Give away their logon name

and password

The Results

6 people are duped

Give away their logon name

and password

In order to read a news story

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6 people are duped

Give away their logon name

and password

In order to read a news story

The Response

Containment

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The Response

Containment

2 Factor authentication

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Containment

2 Factor authentication

The Response

Containment

2 Factor authentication

Followed by a huge education

and awareness effort

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Containment

2 Factor authentication

Followed by a huge education

and awareness effort

What Was Included

Email to all employees

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What Was Included

Email to all employees

Internal blog entries

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Email to all employees

Internal blog entries

What Was Included

Email to all employees

Internal blog entries

Updates to awareness training

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Email to all employees

Internal blog entries

Updates to awareness training

What Was Included

Email to all employees

Internal blog entries

Updates to awareness training

Leverage the grape vine

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Email to all employees

Internal blog entries

Updates to awareness training

Leverage the grape vine

Segway to 30 days later

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Pentester Hired

Measure results of education effort

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Pentester Hired

Measure results of education effort

Mass email phishing test sent

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Measure results of education effort

Mass email phishing test sent

The Results

Good news!

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The Results

Good news!

An order of magnitude improvement

in people reporting the attack

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Good news!

An order of magnitude improvement

in people reporting the attack

The Results

Bad News!

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The Results

Bad News!

6 people failed the test

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Bad News!

6 people failed the test

The Results

Bad News!

6 people failed the test

It’s a different 6 people

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Bad News!

6 people failed the test

It’s a different 6 people

6 = 6

What Did Life Teach Me?

You Can Never Save Everyone

Strive for 100% but have realistic

(cost effective) expectations

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You Can Never Save Everyone

Strive for 100% but have realistic

(cost effective) expectations

What I Now Do Differently

Awareness training is good

A reward system motivates people to

leverage what they learned

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Awareness training is good

A reward system motivates people to

leverage what they learned

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We have an Internet policy…But not a Bring Your Own Device policy.

Case Study #4

Product security evaluation

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Product security evaluation

The Setup

Contracted by a bank

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The Setup

Contracted by a bank

Evaluate a new system they are

considering for purchase

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Contracted by a bank

Evaluate a new system they are

considering for purchase

The Setup

Contracted by a bank

Evaluate a new system they are

considering for purchase

Hired to evaluate security

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Contracted by a bank

Evaluate a new system they are

considering for purchase

Hired to evaluate security

The Evaluation

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The Evaluation

Worst system ever!!!

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The Evaluation

Worst system ever!!!

Hybrid that combines Windows

and a mini computer

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Worst system ever!!!

Hybrid that combines Windows

and a mini computer

The Evaluation

Worst system ever!!!

Hybrid that combines Windows

and a mini computer

Got root 3 times in 20 minutes

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Worst system ever!!!

Hybrid that combines Windows

and a mini computer

Got root 3 times in 20 minutes

0wn3d During Preso

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My Write Up

Most pointed review I’ve written to date

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My Write Up

Most pointed review I’ve written to date

Documented why the architecture was

horribly flawed

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Most pointed review I’ve written to date

Documented why the architecture was

horribly flawed

My Write Up

Most pointed review I’ve written to date

Documented why the architecture was

horribly flawed

Can’t be patched!

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Most pointed review I’ve written to date

Documented why the architecture was

horribly flawed

Can’t be patched!

Quick Factoid!

The word “horrible” has over 50

synonyms

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Quick Factoid!

The word “horrible” has over 50

synonyms

It is actually possible to use them all

in a single professional documents

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The word “horrible” has over 50

synonyms

It is actually possible to use them all

in a single professional documents

How The Bank Responded

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How The Bank Responded

They purchased the system

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How The Bank Responded

They purchased the system

And opted for the premium support

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They purchased the system

And opted for the premium support

How The Bank Responded

They purchased the system

And opted for the premium support

Contract had already been signed

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They purchased the system

And opted for the premium support

Contract had already been signed

Convo With The Bank

Me: Which part of “horribly insecure”

did you not understand?

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Me: Which part of “horribly insecure”

did you not understand?

Convo With The Bank

Bank: But we can migrate the data

without any conversion costs!

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Bank: But we can migrate the data

without any conversion costs!

Convo With The Bank

Me: Sounds like you made up your

mind ahead of time. Why did you

have me evaluate the system?

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Me: Sounds like you made up your

mind ahead of time. Why did you

have me evaluate the system?

Convo With The Bank

Bank: We hoped you would like it.

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What Did Life Teach Me?

Not everyone understands

“Security Speak”

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Not everyone understands

“Security Speak”

What I Now Do Differently

Tailor to your audience: Convert

“security speak” to “risk” and

“financial” lingo

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Tailor to your audience: Convert

“security speak” to “risk” and

“financial” lingo

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We collect system logs…but no one actually looks at them

Case Study #5

The Epic battle of good and evil…

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The Setup

DNS SaaS company

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The Setup

DNS SaaS company

Offers a “dynamic DNS” product

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DNS SaaS company

Offers a “dynamic DNS” product

The Setup

DNS SaaS company

Offers a “dynamic DNS” product

Great solution for cloud users

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DNS SaaS company

Offers a “dynamic DNS” product

Great solution for cloud users

The Setup

DNS SaaS company

Offers a “dynamic DNS” product

Great solution for cloud users

Unfortunately can be used for evil

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DNS SaaS company

Offers a “dynamic DNS” product

Great solution for cloud users

Unfortunately can be used for evil

How The Bad Guys Operate

Build an infrastructure of “Command

and Control” servers

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How The Bad Guys Operate

Build an infrastructure of “Command

and Control” servers

These manage infections and propagate

malware

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Build an infrastructure of “Command

and Control” servers

These manage infections and propagate

malware

How The Bad Guys Operate

Build an infrastructure of “Command

and Control” servers

These manage infections and propagate

malware

The “brains” of the setup

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Build an infrastructure of “Command

and Control” servers

These manage infections and propagate

malware

The “brains” of the setup

C&C Infrastructure

Designed to be fault tolerant

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C&C Infrastructure

Designed to be fault tolerant

Kill one server, the rest take up the slack

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C&C Infrastructure

Designed to be fault tolerant

Kill one server, the rest take up the slack

Dynamic DNS provides redundancy if

server is blocked or taken down

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Designed to be fault tolerant

Kill one server, the rest take up the slack

Dynamic DNS provides redundancy if

server is blocked or taken down

C&C Infrastructure

Designed to be fault tolerant

Kill one server, the rest take up the slack

Dynamic DNS provides redundancy if

server is blocked or taken down

Can recover when a few servers are lost

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Designed to be fault tolerant

Kill one server, the rest take up the slack

Dynamic DNS provides redundancy if

server is blocked or taken down

Can recover when a few servers are lost

Old IR Methodology

Block the account

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Old IR Methodology

Block the account

Black hole the host names

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Block the account

Black hole the host names

Old IR Methodology

Block the account

Black hole the host names

Problem: If you don’t get the

whole C&C network it can recover

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Block the account

Black hole the host names

Problem: If you don’t get the

whole C&C network it can recover

New IR Methodology

Research the account

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New IR Methodology

Research the account

Help innocent clients recover their

system from infection

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Research the account

Help innocent clients recover their

system from infection

New IR Methodology

Research the account

Help innocent clients recover their

system from infection

When evil, play cat and mouse

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Research the account

Help innocent clients recover their

system from infection

When evil, play cat and mouse

New IR in Practice

Account created from Russia

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Account created from Russia

New IR in Practice

Account created from Russia

Ticked boxes as a suspect account

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Account created from Russia

Ticked boxes as a suspect account

New IR in Practice

Account created from Russia

Ticked boxes as a suspect account

12+ scripted host names created

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Account created from Russia

Ticked boxes as a suspect account

12+ scripted host names created

New IR in Practice

Account created from Russia

Ticked boxes as a suspect account

12+ scripted host names created

Fingerprint of Neutrino actors

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Account created from Russia

Ticked boxes as a suspect account

12+ scripted host names created

Fingerprint of Neutrino actors

Time For Some Fun

Let them create their servers

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Let them create their servers

Time For Some Fun

Let them create their servers

Gave them time to deploy iframes

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Let them create their servers

Gave them time to deploy iframes

Time For Some Fun

Let them create their servers

Gave them time to deploy iframes

Let servers get integrated into C&C

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Let them create their servers

Gave them time to deploy iframes

Let servers get integrated into C&C

Time For Some Fun

Let them create their servers

Gave them time to deploy iframes

Let servers get integrated into C&C

Pointed their hosts at honeypots

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Let them create their servers

Gave them time to deploy iframes

Let servers get integrated into C&C

Pointed their hosts at honeypots

Impact of Redirection

Broke some C&C functionality

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Impact of Redirection

Broke some C&C functionality

ID 30+ other C&C servers

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Broke some C&C functionality

ID 30+ other C&C servers

Impact of Redirection

Broke some C&C functionality

ID 30+ other C&C servers

Block 140,000 infections

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Broke some C&C functionality

ID 30+ other C&C servers

Block 140,000 infections

Impact of Redirection

Broke some C&C functionality

ID 30+ other C&C servers

Block 140,000 infections

Collect new data on functionality

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Broke some C&C functionality

ID 30+ other C&C servers

Block 140,000 infections

Collect new data on functionality

What We Did Next

Warn C&C owners of infection

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What We Did Next

Warn C&C owners of infection

Analyze previously unknown data

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Warn C&C owners of infection

Analyze previously unknown data

What We Did Next

Warn C&C owners of infection

Analyze previously unknown data

Share data with the community

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Warn C&C owners of infection

Analyze previously unknown data

Share data with the community

What We Did Next

Warn C&C owners of infection

Analyze previously unknown data

Share data with the community

Update our detection

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Warn C&C owners of infection

Analyze previously unknown data

Share data with the community

Update our detection

What The Bad Guys Did Next

What they always do

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What they always do

What The Bad Guys Did Next

What they always do

Try to set their network back up

Pg. 134 Security Through Absurdity: Lessons Learned @chris_brenton

What they always do

Try to set their network back up

Segway to 6 hours later

Bad guys come back

Pg. 135 Security Through Absurdity: Lessons Learned @chris_brenton

Segway to 6 hours later

Bad guys come back

Using different account credentials

Pg. 136 Security Through Absurdity: Lessons Learned @chris_brenton

Bad guys come back

Using different account credentials

Segway to 6 hours later

Bad guys come back

Using different account credentials

Same fingerprint

Pg. 137 Security Through Absurdity: Lessons Learned @chris_brenton

Bad guys come back

Using different account credentials

Same fingerprint

Segway to 6 hours later

Bad guys come back

Using different account credentials

Same fingerprint

Start spinning up new C&C servers

Pg. 138 Security Through Absurdity: Lessons Learned @chris_brenton

Bad guys come back

Using different account credentials

Same fingerprint

Start spinning up new C&C servers

Lather, Rinse, Repeat

We let them setup their C&C

network

Pg. 139 Security Through Absurdity: Lessons Learned @chris_brenton

We let them setup their C&C

network

Lather, Rinse, Repeat

We let them setup their C&C

network

Then take it all away

Pg. 140 Security Through Absurdity: Lessons Learned @chris_brenton

We let them setup their C&C

network

Then take it all away

Lather, Rinse, Repeat

We let them setup their C&C

network

Then take it all away

This repeats a third time

Pg. 141 Security Through Absurdity: Lessons Learned @chris_brenton

We let them setup their C&C

network

Then take it all away

This repeats a third time

Don’t Go Away Mad…

Bad guys relocate to Central

America service provider

We warn the provider

C&C network has yet to recover

Pg. 142 Security Through Absurdity: Lessons Learned @chris_brenton

Bad guys relocate to Central

America service provider

We warn the provider

C&C network has yet to recover

What Did Life Teach Me?

Remember as you watch this film

Pg. 143 Security Through Absurdity: Lessons Learned @chris_brenton

What Did Life Teach Me?

Remember as you watch this film

When things appear their darkest

Pg. 144 Security Through Absurdity: Lessons Learned @chris_brenton

Remember as you watch this film

When things appear their darkest

What Did Life Teach Me?

Remember as you watch this film

When things appear their darkest

Evil may win some of the battles

Pg. 145 Security Through Absurdity: Lessons Learned @chris_brenton

Remember as you watch this film

When things appear their darkest

Evil may win some of the battles

What Did Life Teach Me?

Remember as you watch this film

When things appear their darkest

Evil may win some of the battles

Good always wins the epic war

Pg. 146 Security Through Absurdity: Lessons Learned @chris_brenton

Remember as you watch this film

When things appear their darkest

Evil may win some of the battles

Good always wins the epic war

Thanks For Attending!

cbrenton@dyn.com

@Chris_Brenton

Pg. 147 Security Through Absurdity: Lessons Learned @chris_brenton

cbrenton@dyn.com

@Chris_Brenton