MacSysAdmin 2014 - OS X Server

You absolutely need anti-virus protection on Mac… Well, don't be ... A hacker to me is someone creative who does wonderf
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Better Safe Than Sorry Security and OS X

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SECURITY An Unexpectedly long Journey…

Agenda •

Threats



Protection



Configurations



“Best Practices?”





Let’s talk security

Distrust and causion are the parents of security Benjamin Franklin

Then… •

No viruses



No malware



Secure by design



and of course very cool…

Once the market share starts growing, then… There are definitively viruses for Mac out there…

Well, don’t be stupid… Windows users are more aware of security, i.e. more secure…

I have ”friends” who knows how it’s done …

You absolutely need anti-virus protection on Mac…

Now… •

Gatekeeper



Application Sandboxing



Malware Detection



Full Disk Encryption





Apple Security •

Device Security



Platform Security



Data Security



Network Security

Apple Security Philosophy •

Ease of use



Guide the users



Secure defaults



Freedom to choose

In the Hacker Toolbox ”the quieter you become, the more you are able to hear”

A hacker to me is someone creative who does wonderful things Sir Tim Berners-Lee

Who’s the Hacker? •

Hacking for fun



Hacking for profit



Governments





Tools of the trade •

nmap



Wireshark



Cain & Able



John the Ripper



Metasploit





® metasploit

Demo Playing with fire

Device Security Securing the box

Amateurs hack systems, professionals hack people Bruce Schneier

Device Security •

EFI firmware password



iCloud locking



Configuration profiles



Policy management





Firmware Password •

UI tool on the Recovery HD

Firmware Password •

UI tool on the Recovery HD



Prevents modifier keys



setregproptool -m full



What if you forget it…?!

iCloud Locking •

iCloud / Find My iPhone



Can only use 4 digit code



Survives reboot / reset pram

iCloud Locking •

iCloud / Find My iPhone



Can only use 4 digit code



Survives reboot / reset pram



…but is it secure?

Demo Setting a Firmware Password

Platform Security Securing the processes

People who are serious ’bout software should make their own hardware Alan Kay

Platform Security •

Application Sandboxing



Code Signing



Gatekeeper



XProtect & Quarantine





Mandatory Access Control •

Application Sandboxing



Entitlements



sandbox-exec -n





openBSM Audit •

Logging above and beyond…



system events and user events



praudit for reading audit trails





Demo Roll your own IDS

Data Security Securing the information

There is no castle so strong that it cannot be overthrown by money Cicero

Data Security •

Full Disk Encryption



Keychain Access / iCloud Keychain



Encrypted Containers



Secure Erase





FileVault 2 •

Rich Trouton has the full story



derflounder.com

FileVault 2 •

Rich Trouton has the full story



derflounder.com



What about performance…?!

before…

FileVault 2 •

Rich Trouton has the full story



derflounder.com



What about performance…?!

after…

Encrypted Container •

Disk Utility or hdiutil



128 or 256-bit encryption



Password in a keychain



Password in an external keychain





Demo A ”poor mans” 2-factor authentication

Network Security Securing the traffic

Users will take dancing pigs over security everytime Bruce Schneier

Network Security •

Encrypted traffic



Encrypted authentication



Firewalls





Firewalls •

Application Layer



Simple UI setup



Packet based IPv4 & IPv6



CLI or IceFloor 2





Demo Computer Lockdown, extraordinaire

Encryption Primer Talk is cheap, …if unencrypted

Meet our friends…

Eve Alice Bob

Yes, it’s apple123

Clear text is not a secure way of transmitting secrets on a network…

Do you have the password?

Yes, it’s apple123

Clear text is not a secure way of transmitting secrets on a network…

pwnd!

Thank you!

Yes, it’s ********

We really need to encrypt any secret information before it is sent…

Do you have the password?

Yes, it’s ********

We really need to encrypt any secret information before it is sent…

?

?

Yes, it’s ********

…but, how do we share encryption keys without everyone on the network getting them?

?

?

Let’s do DHX Diffie Hellman Exchange

Do you have the password?

Here’s (x1) Diffie Hellman Exchange Secret * p1 = x1 ! !

Here’s (x1) Diffie Hellman Exchange Secret * p1 = x1

!

x1 * p2 =! x2 !

!

OK, here’s (x2)

OK, here’s x3 Diffie Hellman Exchange Secret * p1 = x1

!

x1 * p2 =! x2 !

! x2 / p1 =! x3

OK, here’s (x2)

OK, here’s x3 Diffie Hellman Exchange Secret * p1 = x1

!

x1 * p2 =! x2 !

x2 / p1 =! x3 !

x3 / p2 = Secret

$#*!…

Thanx!

Crack the Code What is the password on
 the encrypted USB-stick?

Diffie Hellman Exchange… lite Alice first send x1 = 22 729 to Bob… Bob send x2 = 250 019 back to Alice… Alice then send x3 = 14 707 back to Bob…

x1 = secret * p1 x2 = x1 * p2 x3 = x2 / p1 x3 / p2 = secret

”It can only be attributable to human error…” HAL 9000

Practice what you learn

Can you hack it? Setup with security in focus

Can you read the content in
 the PDF in the Shared folder?

Security Setup •

Firmware Password - setregproptool -m full



FileVault2 Encrypted



Secure Container - 256-bit encrypted



Password stored in external keychain



Encrypted PDF



All passwords 22 characters





”Dave, this conversation can serve no purpose anymore…”

Goodbye