Encrypting Email with Enlocked

In my last post for Law Technology Today, I wrote about BoxCryptor and encrypting documents stored in Dropbox and SkyDrive: Encryption in the Cloud: BoxCryptor  As you know from that post, I was impressed with BoxCryptor, but I was still searching for an easy way to encrypt emails sent from my Gmail account, which is web-based.   I was therefore excited to read Robert Ambrogi’s posts at LawSitesblog.com — Email Encryption, Made Idiotically Easy and Update on Enlocked, the Easy Email Encryption Tool, which brought to my attention Enlocked.  As noted by Robert Ambrogi, Enlocked can be used with Microsoft Outlook as a plug-in, but for my purposes, it needed to work easily with Gmail.  So, I had to test for myself.   I am happy to report that, with one exception, Enlocked has provided me an easy and, for me, free way to ensure my Gmail is encrypted.

I access my Gmail account through either Chrome or Internet Explorer.   To test Enlocked I downloaded and installed extensions for both browsers without a hiccup.  Following the download, I had to close the browser, reopen the browser, open Gmail, and compose a message.  I now have a button in my Compose box to “Send Secure”:


I have found that one of the most difficult things about encrypting emails is to make opening the encrypted email easy for the recipient.   I have to say I also find that you simply cannot make all recipients happy in how they access the encrypted emails, but we can make it as easy as possible.  Making the assumption that my recipient would not have Enlocked on their computer or mobile device, I sent an encrypted email with a PowerPoint attachment  to a second Gmail account, my primary email account that I access in Microsoft Outlook, and an email to open on my iPhone and iPad.  (Unfortunately I do not have an Android device to test.)

When sending an encrypted Gmail message to the various accounts I received the following message in most of my test accounts:


Accessing the encrypted email through a secondary Gmail account was painless, requiring no additional downloads.  PowerPoint opened up immediately.   Accessing the encrypted email on my iPad and iPhone was slightly more work.  I was forced to download the Enlocked app from the iTunes store, associate the app with my Gmail account, and then open the email.  The installation and access to the Gmail accounts was easy on my iPad, but I could not easily associate both Gmail accounts with Enlocked on my iPhone.   I also had problems accessing the encrypted email  in Outlook 2010 on a Windows 7 machine.   There I only received the following message:


The Enlocked email support quickly responded to my initial request for help with Outlook and is investigating the issue.  Despite the few issues I experienced with Microsoft Outlook and on my iPhone I was impressed with the ease of installation and usability.   The program is free for up to 10 encrypted emails a month and $9.99 per month, or $99.00 annually, for up to a 100 encrypted emails.

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