Notes on macOS Sierra

I’m now just over a fortnight into using Apple’s macOS Sierra, and I can report that it’s not enough time to get used to that name’s oddball capitalization. The past two weeks have, however, allowed me to come to some conclusions and form some questions about this operating-system update.

macos-sierra-logoThe pleasant disk-space mystery: Both times I’ve installed Sierra–an uneventful 50 minutes on my 2012 MacBook Air, an absurd three hours and change on my 2009 iMac–the OS has rewarded me with multiple gigabytes of free space. The MacBook, which was getting so close to full that I had to delete several gigs’ worth of data to install Sierra at all, gained 17 GB, while the iMac got an extra 18 GB back.

I do have the MacBook set to back up its Documents and Desktop folders to iCloud (neither contain enough data to threaten iCloud’s meager 5 GB quota of free space), but that comes nowhere near explaining the newly-liberated volume. And although Sierra doesn’t count “purgeable” files–synced files and media, rarely-used fonts and dictionaries, and other items that the system can always re-download after deletion–the totals of purgeable data listed in the info boxes for each startup disk don’t come close to explaining the discrepancy either.

macbook-storage-about-boxUniversal Clipboard is kind of magical: When I copy something from my iPad, I can paste it into my MacBook and vice versa. This wireless copy-and-paste feature neatly solves an everyday problem of switching between a mobile device and a “real” computer, and the fact that it’s happened with zero fuss amazes me. (I hope I haven’t just jinxed it.)

My iMac, however, is cut off from Universal Clipboard, as it’s a good three years too old. Once again, Apple: I’ll think about buying a new model when you don’t charge me 2016 prices for designs barely changed from 2014.

Search snafus: On both computers, a search in the Calendar app for events that I know exist–like conferences I’ve attended every year since 2010–now fails to show results older than late 2014 in my Google-hosted calendars. Sierra knows these older events exist, because Spotlight searches still find them. A post in Apple’s tech-support forums cites an unnamed Apple rep as saying this is a bug that should be fixed, which I hope is true. I also hope somebody in Apple PR replies to the e-mail I sent Wednesday asking about this.

Meanwhile, Mail has developed its own annoying habit of bouncing back to the oldest messages in my inbox after I cancel out of a search. I trust that’s a bug too, because I cannot think of many search use cases that conclude with the user thinking “now I would like to see my correspondence from 2011.”

siri-in-sierraStuff I haven’t tried much yet: I know that Siri leads off Apple’s pitch for Sierra, but I only really need one personal-assistant app–and that app serves me best on the device I carry most often, my Android phone. I also have yet to try out Apple Pay on the Web, although that’s mainly a factor of me not buying anything online in the past two weeks aside from one quick Amazon purchase. The new auto-categorization features in Photos sound neat but can’t help the overwhelming majority of my photos taken on my Android phone, which never even show up there. The same goes for the souped-up conversation options in Messages (did I mention I use an Android phone?).

Things unfixed or newly broken: Sierra seems as powerless as its predecessor OS X El Capitan when Safari or Chrome decide they want to gobble up every last morsel of memory on the machine. I sure do wish this operating system would remember that
pre-emptive multitasking” was one of its foundational features. It also annoys me that Photos persists in the user-hostile practice of discarding the title, description and location I added earlier to a photo when I try to export it to Flickr.

Meanwhile, Sierra has broken the GPGMail plug-in I use to encrypt and decrypt the occasional e-mail–something I only realized after I’d installed this OS on both Macs. I e-mailed the developers and got a reply explaining that Apple made non-trivial changes to the Mail app’s internal code (I wouldn’t have guessed, since Mail seems as glitch-prone as ever) that they realized late in the game would require rewriting the plug-in. So if you were going to send me an encrypted e-mail critiquing this post, please hold off until they can ship a Sierra-compatible beta.

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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…

When I will delete your e-mail

I’ve been making one of my periodic attempts to catch up on my e-mail (read: if you wrote me three weeks ago, your odds of getting a reply sometime this coming week are less worse than usual). That process has required me to think about something I normally avoid: deleting e-mail.

Paper in trash canMy usual habit is to keep everything that’s not outright spam, just in case I might need to look it up later on. Messages from friends and family are of obvious importance, reader e-mail may provide early evidence of a problem that becomes widespread months later, and correspondence from co-workers can have documentary value about a company’s progress or decline. Even PR pitches can have lingering usefulness, by providing the contact info that too many companies can’t think to post on their own sites.

And yet if a search will yield hundreds of messages including the same keyword, I’m going to have a hard time locating the one or few messages I had in mind. Something’s got to go.

The easiest items to delete are the automated notifications and reminders I get from various services I’ve signed up–Twitter, Eventbrite and Meetup, I’m looking at you. The utility of those messages to me usually expires within 24 hours, tops. When those notifications duplicate the ones that already pop up on my phone. my tablet or OS X’s Notification Center, they’re pointless from the moment of their arrival.

(You may have seem this kind of requested, not-spam mail labeled bacn. Not long after that term came about, I wrote that “dryer lint” would be more descriptive and less cutesy, but everybody seems to have ignored that suggestion.)

 

Then come newsletters that attempt to recap headlines in various categories. Even if I read these almost every day–the American Press Institute’s Need to Know and Morning Consult’s tech newsletter come to mind–they’re little help to me the day after, much less six months down the road. I look for day- or months-old news headlines on the Web, not in my inbox.

Ideally, I could set a filter in my mail client to delete designated notifications and newsletters 24 or 48 hours after their arrival. But although Gmail will let you construct a search like that using its “older_than” operator to scrub stale Groupon offers from your inbox, its filters don’t seem to include that option. And the filters in Apple’s Mail, which don’t seem to have been touched by any developers in the last five years, are of no use in this case either.

Do any other mail clients offer this capability? If not, any interested mail developers are welcome to consider this post a formal feature request.

 

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…

Weekly output: Facebook experiment (x2), Supreme Court, best tech, Tech Night Owl, extra e-mail addresses

I sure wish July 4 would fall on a Friday more often–although I can deal with it landing on a Thursday too.

BBC WHYS page6/30/2014: Has Facebook done anything wrong?, World Have Your Say

This BBC program (er, programme) had me on via Skype to discuss Facebook’s 2012 experiment in making about 690,000 users’ News Feeds slightly happier or sadder to see how they’d react. The restrained tenor of the conversation had me thinking this story would not be kicking around six days later; that was a mistake.

7/1/2014: Aereo and Cellphone Searches: High Court Goes in Opposite Directions on Two Key Cases, Yahoo Tech

The Supreme Court released its Aereo ruling at about the worst possible time for me–the day after last week’s column ran, and right before the Google I/O keynote. But waiting until this Tuesday to opine allowed me to cover some subsequent developments and develop a comparison of that case with the court’s far more thoughtful treatment of a different tech-policy issue–whether police need a warrant to search the contents of your phone.

7/1/2014: Yahoo Tech’s Absolute Favorite Tech Stuff of 2014 (So Far), Yahoo Tech

I contributed a couple of nominations to this listicle.

7/1/2014: Facebook experiment, Al Jazeera

The news network’s Arabic-language channel had me on to talk about Facebook’s “emotional contagion” study. If you had a chance to watch it (sorry, I don’t think the clip is available online), did the live translation make me sound any smarter?

7/5/2014: July 5, 2014 — Kirk McElhearn and Rob Pegoraro, Tech Night Owl

Shockingly enough, host Gene Steinberg and I did not discuss the Facebook experiment on this week’s episode of his podcast.

7/6/2014: Mail it in: Get a second address for your main account, USA Today

An exchange on the Internet Press Guild mailing list taught me this one weird trick with e-mail that had somehow escaped my attention until now, then led to this how-to column. As I type this, my link to the column from my public Facebook page has gotten vastly more engagement than anything else I’ve posted there lately, and I have no idea why. If only I could conduct some sort of study about people’s emotional responses to Facebook…

When do you decide it’s time to fire an app?

I guess I don’t have to drag the icon for Apple’s Mail program out of the Dock after all.

Mail iconAn update shipped Thursday fixed the ugly Gmail-synchronization bug that I had been displeased to confirm in OS X Mavericks. Until then, I was about 90 percent sure that I’d have to dump the e-mail app that had been my daily driver since abandoning Eudora on the Mac at least a decade ago.

The likeliest replacement was Airmail, except its lack of support for the nifty data-detectors feature that lets me create calendar events from mentions of dates or times in messages had held me back.

Also, I’m really slow to move from one app to another, to the point that seemingly minor feature requirements like that become an enormous obstacle.

I still have Safari as my default browser in OS X, even though Chrome does a lot of things better–aside from automatically filling in contact information from my Contacts entry. And I continue to use iPhoto for my pictures, despite its glitches and Apple’s apathy about fixing them (although with 55 GB of photos, moving to a new photo-management app would be a non-trivial endeavor).

About the only major app that has exited my workflow in recent years is Microsoft Word. But since I’d have to pay for a no-longer-so-current version of that–while either Google Docs or TextEdit augmented by WordService provide all the tools I need for my formatting-free writing, leaving Apple’s Pages sufficient for the occasional venture into graphic design–that was a much easier call to make.

What was the last program you fired for cause? Tell me about it in the comments.