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.

 

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El Capitan errata

Ten days ago I upgraded my MacBook Air to Apple’s new OS X El Capitan, and a day later I did the same on this iMac. The experience has been a little rocky so far:

El Capitan beachball cursor• I’m still seeing the spinning-beachball cursor way too often, and for steps that shouldn’t particularly tax either computer’s processor or flood its memory. Having it look different does not help.

• While Mail no longer randomly bounces me months back in a particular folder when I select it, it’s exhibiting a more annoying malfunction: When I move or delete messages in either of my Google Apps accounts, they pop back into their original inbox for a moment before being swept away a second or too later.

• Time Machine still can’t do math. On this iMac, it’s complaining that the backup volume is full–even after I’ve removed more than 150 gigabytes of data from its backup set. Dear Apple: I am not interested in buying a new hard drive because your backup utility doesn’t know how to subtract.

OS X El Capitan about box• Some random malfunction has caused every item in Address Book–both individual contacts and contacts groups–to get duplicated. I’m going to assume this is iCloud’s fault.

• Safari continues to randomly pop tabs into their own separate window. This bug has now persisted through different OS X releases, and I know I’m not the only one to complain about it. Alas, its cause and how to end it remain mysteries to me.

• Safari remains vulnerable to locking up the entire machine when Safari Web Content processes start to gobble memory; short of force-quitting Safari, my only remedy is to bring up Activity Monitor and force-quit the offenders, one at a time. But hey, at least I can finally silence the audio that started randomly playing in some other tab.

I had hoped that this deliberately incremental release of OS X would bring a renewed and overdue focus on software quality in OS X, but so far I’m not seeing it. Are you?

An unwanted weekend of Web-mail

I’ve written before how I’m not too fond of Web-mail versus desktop clients, but last weekend didn’t give me a choice in the matter.

Gmail offline UI detailAbout an hour after my flight took off, my MacBook Air coughed up an error message from the Mail program that its index had gotten scrambled (not the exact phrasing; I inexplicably forgot to take a screengrab) and needed to be rebuilt. Fine, I said, and clicked the appropriate button.

Less than an hour later, my aging laptop complained that it was out of space. After a couple of fruitless attempts to weed out larger files, I gave up on mail for the rest of the way to LAX, then resigned myself to using the Webmail interface to the Google Apps account I use for work.

In the two years since Apple’s Mail app last couldn’t connect me to my work account, Gmail hasn’t changed much but Apple’s Mail app has. It’s become a clumsy, clanky, sluggish part of my workflow that usually has me grumbling in complaint before I’m halfway through the first cup of coffee.

Sadly enough, I still missed Mail. Gmail’s regular view only shows 15 messages on my MacBook’s screen, and its in-browser offline mode–a non-negotiable item given the horrible state of the ONA conference WiFi–only showed eight at a time.

Mail unsuccessful setupMy usual method of policing my inbox, block-selecting non-essential messages and moving them to folders like “PR” or “Administrivia,” broke down when Gmail Offline showed that few messages and required me to select each one individually before any moves to sub-folders.

Gmail’s automatic classification of messages under tabs like “Promotions” and “Social” didn’t help aside from correctly shunting most of the PR correspondence to the former tab.

At no point over that weekend did I get WiFi fast enough to let me even think about re-syncing over a dozen gigabytes of mail back down to my laptop–at one point, Mail couldn’t even crawl through its first setup screen. So I limped along in Web-mail, steadily fell behind, and have since caught up slowly in my iMac’s copy of Mail.

As I type this, Apple’s OS X El Capitan just finished installing on that MacBook. Will Mail behave a little better in that new release? I can only hope…

Apple Mail malaise (update)

There’s no program on my Mac that’s annoyed me more over the last year than Mail. Which is funny, because for years I held up that program as an example of Apple working to fix customers’ problems while Microsoft let Outlook Express decay.

Apple Mail about boxBut sometime during the development of OS X Mavericks, Mail went off the rails. It shipped with a bug that made syncing with a Gmail account awkward to implausible. Apple fixed that within weeks, but other problems lingered through many or all of its updates to Mavericks:

  • Searching for old messages was intolerably slow, to the point where it would be faster to grab my iPad, log into the relevant account and start the search… after first running up and down the stairs to find that tablet.
  • Switching back to Mail from other apps would leave the insertion point randomly shifted to a point months or years in the past–which, to be fair, is great for cheap nostalgia.
  • Some mailboxes would be shown sorted by subject instead of date, never mind that sorting by subject is a total waste of time unless a mail client can’t handle search (ahem).
  • More recently, Mail began forgetting the custom app passwords Google generates for mail clients and other apps that can’t process its two-step verification codes.

Apple’s updates fixed some of these issues before OS X Yosemite. I don’t think I’ve seen a mailbox randomly sorted by subject in months, and I haven’t had to open Keychain Access to copy a saved Google app password back into Mail since last month.

Yosemite, to judge from its performance on my MacBook Air, has also returned search in Mail to a state of good repair. I can only hope Apple keeps working on these other issues. Because between Web-mail’s issues with offline access and working with other apps and the lack of a compelling alternative client (understandable, given how many people rely on Web-mail or don’t spend as much time in a mail client as me), firing this app just doesn’t seem too practical.

And at least the prominent mentions of Mail in Apple’s product page for Yosemite suggests the company realizes it can’t leave this app in maintenance mode. If only I could say the same for iPhoto…