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Henry Stamerjohann
Apfelwerk GmbH & Co. KG

Twitter: @head_min
Slack: @henry
hello (again)
Building your macOS Baseline
Requirements
• Wide variety of endpoints in a mobile world
• Mission to secure Hardware / Software configurations

• Continuous Vulnerability Assessment

• We are responsible for data (GDPR / EU-DSGVO)
Today
• You’re asked to apply a Windows Security guideline to Macs

• You’re questioned how Group Policy Objects (GPOs) can apply to Macs

• You’re glued into looping-discussion how MDM / APNs works 

• InfoSec challenges you with: "Why should we trust 17.0.0.0/8"
Imagine
Building your macOS Baseline Requirements MacadUK 2018
Security Baseline
Network 

segmentation
Access control 

management
System auditing
Compartmen-

talization
Physical access
Verify 

digital signatures
Vulnerability 

assessment
Aggregate, 

alert upon logs
Managed 

Updates
Intrusion 

detection
Inventory

Control
Secondary 

factors
Remediation

plan
Components
Platform 

firmware security
Full disc

encryption Forensics
Intrusion 

detection
Network 

segmentation
Access control 

management
System auditing
Compartmen-

talization
Physical access
Verify 

digital signatures
Vulnerability 

assessment
Aggregate, 

alert upon logs
Managed 

Updates
Inventory

Control
Secondary 

factors
Remediation

plan
Components
Platform 

firmware security
Full disc

encryption Forensics
Intrusion 

detection
Network 

segmentation
Access control 

management
System auditing
Compartmen-

talization
Physical access
Verify 

digital signatures
Vulnerability 

assessment
Aggregate, 

alert upon logs
Managed 

Updates
Inventory

Control
Secondary 

factors
Remediation

plan
Components
Platform 

firmware security
Full disc

encryption Forensics
Training
• Basic (security) plan for IT systems

• Identify and implement security measures 

• Complete for operational environment

• Specific implementation documents
Essentials
• Enforce compliance standards

• Appropriate strategy to address security and end-user productivity

• Include (simple) post-incident templates

• Your security posture
Objectives
• Patch your systems and software frequently

• Disable services and limit access where possible

• Ensure configuration settings stay compliant

• Close the gaps when detected & keep improving
Procedures
Creating policies too rigid,
you’ll be taking the risk to fail !
Structure
Example: Security Baseline from CERN
Building your macOS Baseline Requirements MacadUK 2018
Microsoft Security Compliance Toolkit
www.cisecurity.org/benchmark/apple_os/
github.com/drduh/macOS-Security-and-Privacy-Guide
github.com/drduh/macOS-Security-and-Privacy-Guide
• Config Profiles (MDM, manually deployed)

• Scripts / CLI tools / Software

• Conditionals / Extension Attributes

• MDM commands (wipe/lock)
Configuration elements
• Inventory information, management system 

• Scheduled intervals 

• Reporting / Dashboards / Logging

• Change Detection, Alerting

• Automation / programmed remediation
Control Facilities
github.com/kristovatlas/osx-config-check
Building your macOS Baseline Requirements MacadUK 2018
How many binaries and scripts inside?
App Binaries Scripts
Firefox.app
Google Chrome.app
Atom.app
Xcode.app
8
12
30
1224 270
(bash, python, perl, node,..)
144
(bash, python, node,..)
6
(bash)
-
122
Executable Bingo!
support.apple.com/en-us/HT208103
Repercussions
Acknowledge risk of executing malicious binaries 

Developers could blindly insert "bad code" or
"backdoor mechanism", etc.
media.ccc.de/v/34c3-9249-hardening_open_source_development
34C3
Devs …what can go wrong ?
• Flaws in development toolchains

• Risk of code execution

• Package managers (npm, hombrew)

• Code or build scripts compromised

• Hiding code from git diff (UTF-8 Character spoofing) 

• ASCII control characters copy/paste compromised
Executable Bingo!
www.tenable.com/products/nessus/nessus-professional
https://www.inspec.io
Building your macOS Baseline Requirements MacadUK 2018
Building your macOS Baseline Requirements MacadUK 2018
Building your macOS Baseline Requirements MacadUK 2018
brew.sh
Application Lifecycle &
Change management
Inspect content
Fingerprint binaries
OracleJava9-9.0.1.0.11.pkg
Fingerprint binaries
OracleJava9-9.0.4.0.11.pkg
Inspect for difference in detail
Discuss responsibly
Building your macOS Baseline Requirements MacadUK 2018
Security Baseline
(Management infrastructure)
• Configuration management to control server state 

• Build Multiple layers of defense 

• Limit access / API access

• Use logging and intrusion detection
Management services
Local logs
Building your macOS Baseline Requirements MacadUK 2018
Log aggregation
Log aggregation
Log aggregation
http://dev-sec.io
http://dev-sec.io
OSQuery
(Change detection)
https://osquery.io
https://osquery.io
https://osquery.io
Recurring check
Recurring check
Google Santa
(Binary control)
https://github.com/google/santa
https://santa.readthedocs.io/en/latest/
Building your macOS Baseline Requirements MacadUK 2018
Scan executable content
Scan executable content
Scan executable content
Building your macOS Baseline Requirements MacadUK 2018
Building your macOS Baseline Requirements MacadUK 2018
brew-openssl-1.0.2h.json
Diff for analyze
brew-openssl-1.0.2n.json
Event streams
Action
action (clause)
execute once the
probe fires
Event
point of
instrumentation
in the system
Ship
aggregate
results &

sync config
Probe
filter when certain
event (described)
happens
>>> Event stream data is stored for historic inspection
https://zentral.io
github.com/zentralopensource/zentral
Open BSM audit
Open BSM audit
Open BSM audit
http://services.google.com/fh/files/misc/fleet_management_at_scale_white_paper.pdf
Rebuild your
Security Baseline
Data Protection & Regulation
TY!
Q & A
Links
https://github.com/apfelwerk/macadUK2018-baseline-requirements

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