Encryption Made Simple for Lawyers

by Ries, David G.; Simek, John W.; Nelson, Sharon D.

• ISBN13: 9781634250580
• ISBN10: 1634250583
• Format: Paperback
• Copyright: 2016-01-07
• Publisher: American Bar Association

Summary

Encryption is now a generally accepted security measure for protecting confidential data – both when stored and transmitted. Data breaches have become a common occurrence, and hackers cannot only get confidential details about a case or deal, but steal your client's information as well. Fortunately, easy-to-use options are available today for encryption. It has now reached the point where all attorneys should generally understand encryption, have it available for use when appropriate, and make informed decisions about when encryption should be used and when it is acceptable to avoid it. Accomplished authors Sharon D. Nelson, David G. Ries and John W. Simek will cover everything you need to know about encryption, breaking down the myths of security and putting the power to protect sensitive data in your hands. Topics include:

• The basics and history of encryption
• The ethics of encrypting confidential information
• A layman's view of encrypting technology
• Easy to use options for encrypting data on devices like laptops, tablets, and smartphones
• Encrypting data on the go (including wireless and cloud technologies)
• Predictions for the future evolution of encryption

Author Biography

David G. Ries is a member of Clark Hill PLC in Pittsburgh, Pennsylvania, where he practices in the areas of environmental, commercial and technology law and litigation. He has used computers in his practice since the early 1980s and since then has encouraged attorneys to use technology - securely and appropriately.

His environmental practice over the last 40 years has included a broad range of issues in federal and state courts and before administrative agencies, including CERCLA litigation, Clean Water Act litigation, solid and hazardous waste issues, Clean Air Act litigation, storage tank litigation, court and administrative challenges to regulatory programs and defense of penalty actions. His technology practice has included a variety of litigation matters, including major systems implementations, and advising clients on a number of technology law issues such as hardware and software agreements, information security, privacy regulations, records management, e-discovery, and electronic contracting.

Dave frequently speaks and writes on environmental, technology, and ethics issues for legal, academic, and professional groups including the American Bar Association. He is the Editor of e-Discovery 3rd Ed. (PBI Press 2014), a co-author of Encryption Made Simple for Lawyers (American Bar Association 2015) and Locked Down: Information Security for Attorneys (American Bar Association 2012, ISBN: 978-1-61438-364-2), and a contributing author to Information Security and Privacy: A Legal, Business and Technical Handbook, Second Edition (American Bar Association 2011, ISBN: 978-1-61632-807-8) and Information Security for Lawyers and Law Firms (American Bar Association 2006).

Mr. Simek is the Vice President of Sensei Enterprises, Inc., an information technology, digital forensics and information security firm located in Fairfax, VA. Mr. Simek has a national reputation as a digital forensics technologist and has testified as an expert witness throughout the United States. He holds a degree in engineering from the United States Merchant Marine Academy and an MBA in finance from Saint Joseph's University.

Mr. Simek holds the prestigious Certified Information Systems Security Professional (CISSP) and EnCase Certified Examiner (EnCE) certifications in addition to multiple other technology certifications. He currently provides information technology support to over 220 area law firms, legal entities and corporations. He is a co-host of the Legal Talk Network podcast Digital Detectives. He is a frequent author (eleven books published by the ABA, including The 2015 Solo and Small Firm Legal Technology Guide, ISBN: 978-1-63425-074-0, Locked Down: Information Security for Attorneys ISBN: 978-1-61438-364-2, and The Electronic Evidence and Discovery Handbook: Forms, Checklists and Guidelines ISBN: 978-1-59031-670-2, and hundreds of articles) and speaker on legal technology, information security and electronic evidence topics.

Sharon D. Nelson, Esq., is the president of Sensei Enterprises, Inc, a digital forensics, information security and information technology firm in Fairfax, Virginia. Ms. Nelson is the author of the noted electronic evidence blog, Ride the Lightning and is a co-host of the Legal Talk Network podcast series called "The Digital Edge: Lawyers and Technology" as well as "Digital Detectives." She is a frequent author (eleven books published by the ABA, including The 2015 Solo and Small Firm Legal Technology Guide, ISBN: 978-1-63425-074-0, Locked Down: Information Security for Attorneys ISBN: 978-1-61438-364-2, The Electronic Evidence and Discovery Handbook: Forms, Checklists and Guidelines ISBN: 978-1-59031-670-2, and How Good Lawyers Survive Bad Times ISBN: 978-1-60442-573-4, and hundreds of articles) and speaker on legal technology, information security and electronic evidence topics. She is the president of the Virginia State Bar June 2013 June 2014.

Table of Contents

About the Authors. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . xi

Acknowledgments.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . xv

Preface.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . xvii

Chapter 1 Introduction to the Amazing World of Encryption 1

Secret Decoder Ring.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2

Basic Terms.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2

Goal of Encryption. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3

History. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3

Hieroglyphics. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4

Substitution Ciphers.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4

Scytale Cipher.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5

Caesar Cipher.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5

Vigenère Cipher.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6

Jefferson Disk. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7

Zimmerman Telegraph.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8

Enigma.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9

Indian Code Talkers.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10

Historical Footnotes (just for fun). . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10

Modern Day.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10

Chapter 2 Encryption and a Lawyer's Duty to Safeguard Information 13

Ethics Rules. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 14

Ethics Opinions.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 17

Ethics Rules—Electronic Communications.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 20

Ethics Opinions—Electronic Communications. . . . . . . . . . . . . . . . . . . . . . . . . . . 21

Common Law Duties.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24

Laws and Regulations Covering Personal Information.. . . . . . . . . . . . . . . . . . . 24

Summary of Duties.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 27

Information Security Basics.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 28

Encryption and Reasonable Safeguards.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 29

Mobile Devices.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 29

E-mail.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 30

Conclusion. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 32

Chapter 3 Why is Encryption So Important for Lawyers? 33

Data Breaches Have Proliferated!. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 34

The Painful Costs of Data Breaches.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 37

The Ethical Duties of Lawyers are Changing with Technology.. . . . . . . . . . 38

Who is the Real Threat?. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 42

Encryption is Part of the Security Process.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 43

Chapter 4 The Basics of Encryption Technology

(Some Tech Stuff You May Want to Know) 47

The Encryption Process.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 48

Encryption Algorithms.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 56

Authentication, Integrity, and Nonrepudiation. . . . . . . . . . . . . . . . . . . . . . . . . . . . 57

Backup and Key Recovery.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 59

Conclusion. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 60

Chapter 5 Encrypting Laptops, Desktops, and Servers 63

Disk Encryption Basics.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 65

Encryption in Operating Systems.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 67

Windows. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 67

Apple OS X.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 70

Contents vii

Encryption Software.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 71

Laptops.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 72

Desktops.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 73

Servers.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 73

Enterprise Management.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 73

Conclusion. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75

Chapter 6 Encryption for Smartphones and Tablets 77

Secure Setup. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 78

iPhones. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 80

iPads .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 81

Android.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 82

BlackBerry.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 84

Windows. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 84

Mobile Device Management.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 85

Encrypted Compartment for Law Firm Data. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 86

Conclusion—Using the “No-Brainer” Solution.. . . . . . . . . . . . . . . . . . . . . . . . . . . 86

Chapter 7 Encrypting Portable Drives 87

Encrypted USB Flash Drives.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 88

Encrypted External Hard Drives.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 92

Operating System Encryption of Portable Drives. . . . . . . . . . . . . . . . . . . . . . . . . 93

Encryption Software.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 93

Enterprise Management.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 94

Conclusion. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 94

Chapter 8 Network Communications 95

WEP.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 96

WPA.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 98

WPA2. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 99

Using Wireless Networks.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 101

Secure Socket Layer.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 103

TLS .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 106

Link Encryption. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 107

End-to-End Encryption. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 107

Virtual Private Networks (VPN).. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 108

RDP .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 111

Summary. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 112

Chapter 9 Electronic Communications 113

Microsoft Exchange Server. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 114

Outlook Web Access. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 114

Outlook/Exchange. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 115

Gmail. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 117

E-Mail Encryption.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 117

Outlook Messages. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 120

Office 365 Message Encryption. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 123

Secure E-mail Services. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 124

Hushmail.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 126

ZixCorp. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 126

Voltage SecureMail.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 128

Mimecast. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 129

Phone Calls & Text.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 129

Skype. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 130

Video Conferencing. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 131

Practical Steps.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 132

Chapter 10 Cloud Services 133

Dropbox.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 136

Box.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 138

More File Synchronization and Sharing Options.. . . . . . . . . . . . . . . . . . . . . . . 139

SpiderOak.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 139

Viivo .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 142

Boxcryptor.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 144

nCryptedCloud. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 145

Dell Data Protection | Cloud Edition.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 146

iCloud.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 147

Other Cloud Services.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 148

Chapter 11 Securing Documents 151

Microsoft Office.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 152

Adobe Acrobat.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 153

WinZip.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 156

Steganography. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 161

Chapter 12 The Future of Encryption: Through a Glass, Darkly 163

Quantum Physics. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 163

Quantum Computing. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 165

An Encryption Quick Start Action Plan 173

Glossary 177