1SANS Technology Institute - Candidate for Master of Science Degree 1

Deployment of iPads Lessons from the Trenches

Jim HorwathMarch 2012

GIAC GSE, GCUX, GCIA, GCIH, GREM, GSEC, GSIP

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Objective

Overview of the iPad and the effect it will have on business

Security risks of bringing a consumer oriented device such as an iPad into a corporate environment

Security and lack of controls on an iPad - what you need to know

Operational costs and headaches associated with deploying iPads to users

The management nightmare of deploying iPad - patching, securing, keeping users safe from themselves

This is NOT an explanation concerning iPad forensics

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The iPad Storm

• Apple’s incredible sales numbers and market penetration

• Time magazine gave the iPad one of the 50 best inventions of 2010

• Medical, legal, and sales staff were early adopters of iPads

• Apple’s App Store imposes censorship of content causing issues with books and magazines

• Closed system – but still more applications available for iOS than Androids

• No support for flash

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Consumer Device – Security an Afterthought

• Penetration into Fortune 100 companies and other businesses made iPads THE status symbol

Executives see convenience, increased productivity, and freedom

Status symbol cost - This addictive appeal has a cost to it – device + monthly fees

Default configuration has few security controls e.g. No password

Consumers want ease – especially younger users Closed platform - not too much security information

available No anti-virus or malware controls

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Policy Is Your Friend

• Policy will become your best friend – develop early and involve the right people

Acceptable Use Policy (AUP) Change Management Device is meant for employee use only – not spouse,

children or relatives Security Awareness Make users aware of common problems Shoulder surfing – gets worse with complex passcodes

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Security Issues - Strengths

Hardware encryption uses AES 256-bit encryption APIs with the ability to lock-down access Controlled environment with non-jailbroken devices Applications receive a sandbox and are separate from

each other API provides a method for device lock/unlock/password

reset/wipe Implementation and engineering guarded IP secret Cellular communications harder (but not impossible) to

capture Need to test security controls very thoroughly and keep

notes regarding the test results

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Security Issues - Challenges

Limited number of configurable items There are items the user can change and there is no

GPO-like facility to reinforce settings No logging or event log like facility Implementation and engineering guarded IP secret Bluecoat K9 to use as a WEB proxy – but user can

choose not to use it – you have to use a 3rd party product to enforce it

Companies lose control of data – dropbox, Google docs, iCloud

Alphanumeric credentials anywhere on the device echo characters as you type them

No warning or acceptable banner, network connectivity is always on

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Infrastructure Issues

• Where do employees sync devices• Is your corporate infrastructure ready for iTunes

(packaging, updates, etc.)• If iPad users sync to corporate assets, is your storage

and backup environment ready• Is there a business requirement to access internal

resources - example Citrix for applications• Can devices connect internally to wireless infrastructure

– how do you control it• Data leaves daily with employees and their iPads

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Operational Challenges

Keeping iOS current – no mass distribution method iOS 5.0 does allow software updates outside of iTunes Apple provides a low-cost configuration utility iPhone

Configuration Utility (ICU) Mobile Device Management (MDM) software is young Creation of a “Gold Image” is difficult iTunes and corporate acceptance Backing up devices onto personal employee assets –

who owns the data On corporate owned assets does your infrastructure

allow for the additional overhead of iTunes and backups

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More Operational Challenges

Blocking pop-ups -- users cannot change it – blocking pop-ups can stop things like SANS OnDemand from working

Very confusing with some terms: “Auto-Lock” and “Grace-Period”

How do you handle provisioning – corporate vs. personal devices

What happens after employee separation, companies cannot verify

License cost of software is unknown (productivity software for example)

Decreases productivity for some workers

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Hello Help Desk...

• Users are scary• Problems range from common to the bizarre• Calling for device setup – most common• Documentation of common problems should be

available to users• Added cost to train help desk staff on iPad triage• Younger help desk staff are better than older staff due

to familiarity of the technology• Mail stopped and I need it now – the higher up the

food chain the more demanding the user

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Enterprise Management of iPads

Apple provides iPhone Configuration Utility (ICU) – good for just a few devices and proof of concepts

Mobile Device Management (MDM) products are young and lack maturity

Some examples: McAfee, Sybase, Good, AirWatch, BoxTone

Microsoft Active Sync will allow any device with a valid user name and password to connect

Lotus Notes requires granting access to Lotus traveler How does this integrate into your authentication source

LDAP/AD/Domino LDAP/Token Do your homework!

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Mobile Device Management (MDM) Software

• Policy, awareness, education and AUP are critical• Managing a fleet of iPads requires management

software• MDM market place is emerging and not mature• Employees – especially executives - quickly become

“addicted” to an iPad, stability is a key issue• Apple’s closed platform limits what vendors can do –

most vendors do the same thing• Managed service versus in-house, versus hybrid• Managing a fleet of iPads requires management

software

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MDM Lessons

• Survey says e-mail and calendaring are the most important applications to an executive

• Be careful with demonstrations • Negotiations - be prepared for push-back on policies

from executive – they want convenience and not necessarily security

• Field communications is critical – leverage company communications and change management process

• Implement a test environment that is similar to production

• Be careful of firewall rules if using an in-house managed product

• Be very careful with destruction capabilities – a mistake can be career ending

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Summary

Mobile computing is here to stay – learn it, embrace it, and control it the best you can

Mobile computing can give your firm a competitive advantage

Develop policy based on business need and use cases Continual user education and awareness will go a long

way Invest in MDM software to manage devices Avoid being an early adopter