Mail encryption has gotten less cryptic, but some usability glitches linger

I seriously underestimated you all late last year. In a Dec. 7 post about encryption, I wrote that I hadn’t gotten an encrypted e-mail from a reader in years and said I expected that streak to continue.

PGP keysIt did not. Within a week, a dozen or so readers had sent me messages encrypted with my PGP public key (under subject lines like “Have Faith!” and “Challenge Accepted”), and several others have done the same since. That’s taught me that the crypto user experience has, indeed, gotten pretty good in GPG Suite, the Pretty Good Privacy client of choice in OS X.

But at the same time, some awkward moments remain that remind me the woeful state of things in the late 1990s.

Most of the them involved getting a correspondent’s public key, without which I could not encrypt my reply. When it was attached as a file, dragging and dropping that onto the GPG Keychain app had the expected result, but when it came as a block of text in the decrypted message, I (like other users before me) wasted a few mental processor cycles looking for an import-from-clipboard command when I only had to paste that text into GPG Keychain’s window.

I should have also been able to search keyserver sites for a correspondent’s e-mail address, but those queries kept stalling out at the time. One reader did not appear to have a key listed in those databases at all, while I had to remove a subdomain from another’s e-mail address to get his key to turn up in a search.

One more reader had posted his public key on his own site, but line breaks in that block of text prevented GPG Keychain from recognizing it.

The GPGMail plug-in for OS X Mail is in general a pleasure to use. But its default practice of encrypting all drafts meant that I could no longer start a message on my computer and finish it on my phone–and one e-mail that I’d queued up in the outbox while offline went out encrypted, yielding a confused reply from that editor. I’ve since shut off that default.

It’s quite possible that the upcoming stable release of GPG Suite for OS X El Capitan will smooth over those issues. But that version was supposedly almost ready in late September, and there hasn’t been an update on that open-source project’s news page since. I suppose having to wonder about the status of a crucial software component counts as another crypto-usability glitch.


Weekly output: encryption explained, OS X autocorrect, DoubleClick dialog

Yes, I did get your CES PR pitch.

Yahoo Tech crypto FAQ12/7/2015: FAQ: How Encryption Works And Why People Are So Freaked Out About It, Yahoo Tech

The 1.0 version of this column was a detailed look at how encryption works in Pretty Good Privacy and in iOS 8; not for the first time, an editor said I’d gotten too far into the weeds and asked for a rewrite. After this 2.0 version ran, I was pleasantly surprised to have several readers send me PGP-encrypted messages.

If you’d like to know more about this issue, including some of the history behind this debate, see Andrea Peterson’s longer FAQ in the Washington Post.

12/11/2015: Tip: Best Way to Fix OS X’s Autocorrect? Turn It Off, Yahoo Tech

With my USA Today column no longer including a weekly tip at the end, Yahoo was happy to run this tip… which was really more of a rant.

12/13/2015: DoubleClick message should have prompted double take, USA Today

A brief snafu at Google’s advertising subsidiary may not have been sufficient material for a column, but I’d like to think that using it to remind people to be wary of strange requests from even familiar Web sites was a worthwhile exercise.

PGP and me

If you’ve received an e-mail from me in the past week or so, you may have noticed something extra in the message’s headers: an indication that it was digitally signed with my Pretty Good Privacy key.

GPGTools iconAs yet, no recipient has asked about that, much less complimented my digital hygiene or sent a reply encrypted with my PGP public key. Which is pretty much what I expected: The last time I had a PGP setup in operation, I had to ask Post readers to send me an encrypted message before I got any.

A few weeks later, my inbox once again featured only un-encrypted e-mail.

Then some fumbled corporate transitions and the switch to OS X left the open-source MacGPG as the most appealing option on my Mac–and a slow and slowing pace of updates left it an increasingly awkward fit. Without ever consciously deciding to give up on e-mail encryption, I gave up.

(I should have felt guiltier than I did when I offered a Post colleague a tutorial on crypto that I didn’t bother to operate on my own machine. On that note, if you have a key for or in your own PGP keychain, please delete it.)

I finally returned to the fold two weeks ago, when I ducked into a “crypto party” tutorial at the Computers, Freedom & Privacy conference. Jon Camfield of Internews explained that things had gotten a lot better and pointed me to a newer, far more elegant open-source implementation called GPGTools. I downloaded it, installed it, and within minutes had a new set of public and private keys plugged into my copy of Mail (no need to copy and paste a message into a separate decryption app as I did in MacGPG), with my public key uploaded to a keyserver for anybody else to use to encrypt mail to me.

My key ID is 03EE085A, my key fingerprint is FD67 6114 46E8 6105 27C3 DD92 673F F960 03EE 085A, and the key itself is after the jump. Do I expect to get a flood of encrypted messages after this post? Not really. But if somebody does want to speak to me with that level of privacy, they now have an option I should have provided all along, and that’s what counts.

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