Alternatives to Email

• Author: Sean La Roque-Doherty
• Pages: 31-32

OCTOBER 2018 ABA JOURNAL || 31

Business of Law

Alternatives to Email

Lawyers looking for more secure options to

communicate electronically have a number of options

By Sean La Roque-Doherty

when users link matt ers to contacts or

clients. Upon creation, clients a re noti-

fi ed via email with a lin k to access the

portal from a ny internet-related device

to set up a username and pa ssword.

Clients connect to p ortals over an

encrypted S ecure Sockets Layer or

Transport L ayer Security con nection.

The connect ion gives reasonable pro -

tection from eavesd roppers looking for

valuable information and h ackers look-

ing to gain acce ss to remote servers.

Portals allow user s to communicate

with their law yers via messages, up-

load documents and read c ase-related

information , such as documents,

calendar events a nd invoices. Online

portal ser vices can notify client s via

email when data is adde d or changed.

“Secure port als are not as easy to use

as email,” says Mike Frat to, a senior

analyst at 451 Re search, an IT research

and advisor y company. But they “might

be the best option overall,” he says.

“Portals don’t use PGP or S/MIME,

and the commun ications are more or

less contained in the ser vice.”

SECURE COMMUNICATIONS

End-to-end encry pted chat tools

are secure commun ication systems in

which only end users can u nderstand

the communications in t ext, voice or

video format. The encr yption is done

locally on user dev ices, so messages

cannot be read by int ermediary hackers

or even internet providers.

“End-to-end encry pted chat is easy

to use, but both par ties need to use the

same product,” Simek says. “And it is

much more di cult t o preserve, save or

archive the c ommunication session.”

Frank Gillma n, chief information

security o cer at Lewis Brisbois

Bisgaard & Smith hea dquartered in

Los Angeles, ag rees. “Most secure mes-

saging applications have in su cient

complexity of feature s for broader busi-

ness purposes ea rly in their life cycles,”

Gillman says. He add s that the lack of

features “lowers u sage adoption rates

among professionals like law yers.”

“Security concerns, while clearly

viewed as crit ically important, w ill

always place second nex t to the ability

to quickly and e ectively ser vice and

communicate wit h clients,” he says.

THE REPLACEMENTS

Hearing that, I t urned my attention

to end-to-end encry pted chat applica-

tions in which lawyer s and clients have

no option to disable the encry ption

On May 14, security

researchers claimed

to have discovered a

fl aw, called Efail, in

the deployment of

encryption tec hnology in email appli-

cations such as Apple Mail, G mail and

Outlook. The Prett y Good Privacy

encryption st andard and a similar pro-

tocol, S/MIME (Secure/Multipurpose

Internet Ma il Extensions), commonly

used by lawyers to prot ect email from

unauthorized rea ders, were under

attack—but not for the fi rst time.

Security profe ssionals have long

known about the issues w ith PGP, says

John Simek, vice president of Sensei

Enterprises, a d igital forensics and

information secur ity company. “The

real problem is with the w ay that PGP

and S/MIME interact w ith email pro-

grams and the di  culty to properly

confi gure and utilize PGP,” Simek says.

Vendors patched email client appli-

cations a ected by Efai l, but what will

lawyers do the next t ime a fl aw appears

in their email apps th at may compro-

mise client communicat ions?

There are alternat ives to using

encrypted em ail to secure client com-

munications. I’ve found the most prom-

ising are secure onl ine portals such as

those provided by web-ba sed practice

management serv ices from the likes of

MyCase, Rocket Mat ter and Clio and

end-to-end enc rypted messa ging apps.

Beware that chat is a r eal-time com-

munication tool. If you use it like

email, clients may be d isappointed in

your response time. Note th at online

portals ca n contain case-related in for-

mation that obviate s questions and

provides serv ice that clients expect

from professionals: online sel f-service

tools that provide an swers.

Most web-based prac tice manage-

ment services ca n create online portals

Technology

Review

END-TO-END ENCRYPTED CHAT COMPARISON

PRODUCT Signal Wickr Me Wire

Feature

DEFAULT END-TO-END ENCRYPTION √ √ √

MOBILITY SUPPORT FOR AN DROID/IOS √ √ √

DESKTOP SUPPORT FOR MACOS/WIN DOWS √ √ √

ENCRYPTED FILE TRANSFER √ √ √

OFFLINE MESSAGING √ √ √

OPEN-SOURCE SOFTWARE √ No1 √

BACKUP MESSAGE HISTORY √ √ √

EPHEMERAL (time-to-live, disappearing) MESSAGES √ √ √

MESSAGE AND CONVERSATION RECALL (delete on all devi ces) √ √ √

SECURE VOICE/VIDEO/CONFER ENCE CALLING Voice/Video Voice2 Vo/Vi/C onf

SCREENSHOT DETECTION, N OTIFICATIONS No √ No

SYNC MESSAGES ON PHONE AND PC √ √ √

KEY VERIFICATION (verify conversation participants) √ √ √

GITHUB.COM /signalapp /Wickrinc /wireapp/wire

COST Free Free $5 per user/mo

NOTES: 1 Open code bu t not distributed via ope n-source license.

2 Wickr Pro, for $25 per user pe r month, includes voice , video and conferenc e calls. The Pro version supp orts

secure rooms for teams an d projects and the capa bility to set expirati on times for all message s.