1 SANS Technology Institute - Candidate for Master of Science Degree 1 Deployment of iPads Lessons from the Trenches Jim Horwath March 2012 GIAC GSE, GCUX, GCIA, GCIH, GREM, GSEC, GSIP

SANS Technology Institute - Candidate for Master of Science Degree 2 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

SANS Technology Institute - Candidate for Master of Science Degree 3 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

SANS Technology Institute - Candidate for Master of Science Degree 4 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

SANS Technology Institute - Candidate for Master of Science Degree 5 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

SANS Technology Institute - Candidate for Master of Science Degree 6 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

SANS Technology Institute - Candidate for Master of Science Degree

8 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

SANS Technology Institute - Candidate for Master of Science Degree

10 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

SANS Technology Institute - Candidate for Master of Science Degree 11 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

SANS Technology Institute - Candidate for Master of Science Degree 12 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

SANS Technology Institute - Candidate for Master of Science Degree 13 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

SANS Technology Institute - Candidate for Master of Science Degree 14 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!

SANS Technology Institute - Candidate for Master of Science Degree 15 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

SANS Technology Institute - Candidate for Master of Science Degree 16 MDM Lessons Survey says 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

SANS Technology Institute - Candidate for Master of Science Degree

18 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