RocketMatter’s blogLegal Productivity, is running a great two-part post by Carole Levitt and Mark Rosch titled, Lawyers, Encrypted Email, and Gmail. Part 1 discussed the basics of different email encryption systems, and now, Part 2 introduces readers to some specific  encryption tools to make sending Gmail messages more secure.

If you didn’t know, Mark and Carole wrote the book on Gmail for lawyers, so this discussion on encryption is right in their knowledge field.

Google Gmail & Calendar

Part 2 of Carole and Mark’s post discusses SecureGmail, a free Google Chrome extension that every Gmail and Google apps user should install. I’ve had the extension installed for some time, but I honestly haven’t used it that much. I don’t know why, probably because I’m complacent about my security. Admittedly, most email messages I send aren’t that important — “Let’s schedule the deposition for March 20”; “You didn’t respond to discovery” — such that they’d need full-fledged encryption. However, I occasionally send email messages that might deserve a little more protection, especially when related to specific recommendations.

I’m going to take a more active approach at protecting these messages, even if I only achieve farcical satisfaction. Plus, it’s difficult to decipher a message when it looks like this:

Encrypted Email

I think encrypted messages are prudent, even if they’re just tests:

Decrypted Message


But I use MS Outlook

Although I’m trying hard to obliterate the last vestiges of Microsoft Office from my law practice, my desktop-based practice management program requires MS Office to automate documents and store emails. Thus, I’m stuck with Word and Outlook. Side note, I use Google Apps for email and link MS Outlook with Google Apps using the Google Apps Sync for Microsoft Outlook program.

Unfortunately, Outlook doesn’t work with encrypted messages unless you have a secure digital ID. Digital IDs are expensive, and probably too expensive for most people who need to send so few encrypted emails.

I have an acceptable, albeit cumbersome, solution: send the encrypted email message from my Google Apps email account, then go back to Outlook and “Journal” a copy of the encrypted and decrypted messages. This obviously isn’t an ideal method, but SecureGmail is free, and one of the cheapest Outlook ID’s I found was for $90 per year. No thanks.

And what about mobile devices?

Right now, there isn’t any good option for encrypting Gmail messages on a mobile device. You can try DJIGZO S/MIME Email Encryption or my Secure Mail, which I’m testing, and look very promising.

Jeff Taylor

I'm just an ordinary guy living an extraordinary life. I'm also an attorney and I blog about Android for lawyers. You can follow me on Twitter, LinkedIn, YouTube, or Google+.

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