E-mail like it’s 2012: revisiting my Gmail filters

Several months ago, I spent too many hours hacking away at the 18 years’ worth of messages piled up in my Gmail account–because while I could live with paying for extra storage for Google’s backups of my own photos, I’d be damned if I was going to pay to warehouse random companies’ marketing pitches that were eating up far more of my free storage.

Screenshot of Gmail's filter, showing a menu of options that

That experience evidently wasn’t enough fun for me, because over the last couple of weeks I’ve dived into a corner of the Gmail interface I hadn’t spent any sustained time in since… 2012? Fortunately for me, Gmail’s filter interface hasn’t sustained any notable changes in at least that long, judging from how rarely it’s earned a mention in Google’s Gmail blog over the last decade.

Much as in 2012, this dialog lets me choose a message by factors like sender, recipient, subject, content, size and the presence of an attachments. Its next pane allows me to amplify the message’s importance by starring it or marking it as important, apply a label or file it under a category tab, or forward it to to an outside address registered with your Gmail account using an even more fossilized interface.

Those are the basics of e-mail management, and they did suffice to help me craft updated message rules that make my Gmail inbox less chaotic and keep my more consequential correspondence filed away neatly. Less e-entropy is a good outcome.

But the limits of the filtering user experience loom large among Gmail’s missing features. The one I keep coming back to is an equivalent to the “sweep” function in the Microsoft’s Outlook.com that automatically whisks matching messages into the trash 10 days after they arrive. But it’s also crazy that the entire filter UX is imprisoned in Gmail’s Web app–you can neither create nor edit nor view filters in Gmail’s Android and iOS apps, as if the last 10 years of mobile-first computing never reached whatever Googleplex building houses the Gmail developers.

Compare that thin gruel to the thoughtful mail-management tools surfacing in apps that actually have to win customers–I’m thinking here of a new Gmail front end called Shortwave that a team of former Google developers just shipped, but also of the Hey mail service. It’s not hard to think that Google could do a lot more with Gmail if it put serious effort into that work. It’s also not hard to think that Google must feel as comfortable in the e-mail market as Microsoft and Yahoo did before Gmail showed up in 2004.

Google-induced mail migration malaise

A week ago, I learned that one of my longest-running online freebies would end this summer. The seven days since haven’t been enough time for me to decide how to replace the no-charge Google account that’s hosted my home e-mail since early 2010–but they have allowed me to find a reason to dislike each obvious alternative.

Yes, I should have seen this coming. The Google that launched “Google Apps for Your Domain” as a free service in 2006 was a much scrappier firm that could not assume potential customers’ attention. Even in 2010, when I moved my home e-mail to a Google Apps account under a custom domain and set up (just in case!) a work e-mail address under a different custom domain at another Google Apps account, Google hadn’t risen to become an obvious choice for business collaboration.

The Gmail logo under an "Apps" banner, taken from a 2008 Google presentation.

Google did end signups for this free option in December of 2012, but it let existing Apps customers keep their free accounts. That grandfathered, privileged status continued as Google Apps became G Suite in 2016 and then Google Workspace in 2020.

The Google of 2022, however, is a different entity that’s been unplugging other free services. So I was not too surprised to learn that starting July 1, I’d have to pay to keep these two mail accounts hosted–just annoyed to read about this at the 9to5Google blog instead of in an e-mail from Google to me.

I’m fine with paying Google for my work account–make that, paying more on top of what I’ve been spending for extra storage since 2016. A Google Workspace Business Starter account will cost another $6 a month, which is reasonable considering how many other Google services I have tied to this account and how $72 a year would still rank among my cheaper business expenses.

But my home account is just an e-mail account. I don’t use it with Google’s other “workspace” tools; because I keep a separate, standard Gmail account for shopping, banking and other non-work stuff, my home account barely gets used as an e-mail service. Paying $72 a year makes a lot less sense, much less spending that much on addresses I’ve set up for family members who use them even less.

But the options I’ve evaluated first have their own issues:

iCloud+: Since my wife is already paying for extra storage on Apple’s cloud service, I could set up a custom domain there for free. But by associating my home e-mail address with iCloud, I would revive the problem of iPhone-using friends who think they’re using the Messages app to text me on my phone and instead have Apple’s iMessage system silently divert that to the Messages app on my iPad.

Microsoft 365: I already pay for Microsoft’s cloud storage to back up my Windows laptop, and adding multiple e-mail accounts by upgrading to Microsoft 365 Family would add only $30 to my yearly cost. Except Microsoft, for some inane reason that probably looked sharp on a marketing PowerPoint, limits this option to domains hosted with GoDaddy, and that’s not the registar I’ve been content with using for this domain. (One thing I don’t like about this registrar: Their own mail hosting only covers 1 gigabyte of storage per address, which is why they don’t make this list.)

Fastmail: This mail-first service isn’t tied to any larger cloud platform, a simplicity of mission that I appreciate. I also like how I could use this with 1Password to generate “masked,” disposable e-mail addresses for individual services. But with pricing for a custom domain starting at $50 a year per user for 30 GB of storage, this, too, feels like overkill for my own little use case.

Meanwhile, Google may have realized the foolishness of treating every user as one type of business customer. Wednesday afternoon, Ars Technica’s Ron Amadeo flagged an addition to Google’s support note inviting input from people who don’t use legacy Google Apps accounts for work.

Will Google offer a cheaper tier for personal use, and how long will we have to wait to find out? The May 1 deadline Google set for ex-Apps users to choose between upgrading to Workspace or moving their mail elsewhere leaves plenty of time for the indecision-making process to grind on at this company. And among perplexed customers like me.

Two ways your mailing list could be less terrible

Monday’s USA Today column on cleaning out an overloaded Gmail inbox required me to spend an unpleasant amount of time scouring my own inbox to find the most prolific senders. The experience left me mostly convinced of the grotesque selfishness of many e-mail marketing types, but it also yielded some grounds for optimism.

Photo shows a series of bulk-mail stamps

As in, the user experience with some of these companies’ mailing lists let me at least think that they recognized concepts like cognitive load, limited attention span and finite storage space. Here are two practices in particular that I liked:

  • Don’t send promotional e-mails from the same address as order confirmations. This makes it so much easier to find and bulk-delete the sales pitches that no longer carry any relevance–or, if you use Microsoft’s Outlook.com, to set up a “sweep” filter that automatically deletes those messages after a set period of time. Ecco, Macy’s and Staples all seemed to follow this polite, filter-friendly custom.
  • Let me choose how often to get emails–a message a day is often just clingy, but one a week could be less obnoxious–and let me specify what kind of pitches might interest me. Best Buy (“Receive no more than one General Marketing email per week”) and Macy’s (“Let’s Take It Down A Notch—Send Me Fewer Emails, Please”) get the frequency thing right, while L.L. Bean not only lets people choose between weekly, monthly or twice-monthly frequencies but invites them to request only messages about departments like Men’s, Home, or Fishing.

I’d like to close by writing something like “see, it doesn’t have to be this hard”–but a look at my Gmail inbox shows that some of my visits to the mail-preference pages of some retailers hasn’t led to them putting a smaller dent in my inbox. I guess they’d prefer I click their unsubscribe link–or use Gmail’s “block” command.

Weekly output: Google’s password help, Twitter suspensions in Egypt

NEW YORK–This evening finds me here for the Ascent conference, at which I have four panels to moderate Tuesday and things to learn all Monday. Yes, that means I will miss both NLDS games at Nationals Park. Since the team hasn’t done all that well when I’ve been in the stands for a potential division-series clinch, maybe that’s good?

10/2/2019: This new Google tool protects you against dangerous passwords, Fast Company

Along with a fair amount of other tech journalists, I got an advance on Google’s announcement Monday of changes to warn Chrome users about exposed, reused or easily-guessed passwords. Having seen how a similar feature in the 1Password password manager has helped make me less stupid about site logins, I think this is a good move by Google. But I also expect that many users will freak out when they see Chrome telling them that their password has been compromised in a data breach.

10/3/2019: Twitter suspensions in Egypt, Al Jazeera

I appeared on the Arabic-language news channel to talk about reports of Egyptian dissidents’ Twitter accounts being suspended. My take: Twitter has a serious problem with being fooled by coordinated, bad-faith campaigns to get accounts suspended for alleged-but-not-real violations of Twitter’s rules. The anchor then asked why Twitter hadn’t answered AJ’s questions, and I said that most social-media companies are chronically bad at explaining their own decisions. Many have hangups with just speaking on the record.

Weekly output: Google’s 2017 to-do list

The slowest week of the entire year saw only one story appear under my byline. I’ll more than make that up this week as I cover my 20th CES in a row (!). Any gadget news you’d like me to look out for while I’m in Vegas?

yahoo-google-2017-post12/26/2016: OK, Google: Please do these things in 2017, Yahoo Finance

My contribution to Yahoo Finance’s end-of-year coverage was a post about what Google should do in 2017. Will that company follow up on all of my suggestions? Probably not. I’m reasonably confident that we’ll get a better Android Wear watch from Google, that we haven’t seen the last of Google broadband, and that advertising on fake-news sites will take a hit from stricter Google policies. But I’m less confident that Google will ship an end-to-end encryption plug-in for Gmail, and I would be pleasantly shocked to see the firm start selling an ad-free upgrade to Gmail.

 

Weekly output: old TVs, Mark Zuckerberg, rebooting, deleting old e-mail, wireless charging, Android phones, wireless carriers, smartphone features, smart apartments

Another Mobile World Congress went into the books when I flew home from Barcelona Thursday. I’m glad that show and that city have become a regular part of my travel schedule.

2/21/2016: It’s really time to let go of that old tube TV, USA Today

Circling back to a topic I covered in 2013 allowed me to note some good HDTV options for under $200–including the Wirecutter’s $170 pick–and the unfortunate end of Best Buy’s free TV recycling.

Yahoo Tech Zuckerberg MWC post2/22/2016: Zuckerberg at MWC: Getting the World (and Someday His Daughter) Online, Yahoo Tech

The Facebook founder’s Q&A session started at 6 p.m. local time, meaning the press room closed while I was still writing my recap. I finished it on a bench in the hall outside–MWC, unlike CES, has free WiFi throughout the facility.

2/22/2016: Tip: Sometimes You Really Do Need to Reboot the Damn Thing, Yahoo Tech

I’d written this tip item weeks before, not knowing that a colleague had just filed a different tip item around the virtues of rebooting. Fortunately, our devices did not get any less buggy over the ensuing month.

2/23/2016: Tip: How to Quickly and Easily Get Rid of Old E-Mails, Yahoo Tech

You read a version this three and a half years ago at USA Today, but that didn’t give enough credit to Microsoft’s Outlook.com for nailing the task of automatically deleting e-mails over a certain age.

2/23/2016: Why Wireless Charging Is Still a Tangled Mess, Yahoo Tech

Once again, the wireless industry seems dead set on balkanizing itself between two ways to do the same thing.

2/24/2016: Your Next Android Phone: Smaller but Expandable, Yahoo Tech

This was my attempt at a State of the Union address for Android phones.

2/24/2016: Best Wireless Carriers, The Wirecutter

Our first major update to this guide since September factored in the end of two-year contracts at AT&T and Sprint… and two days after it went up, I learned that Sprint had restored two-year contracts. We should have yet another update up in a few days.

2/26/2016: Your next smartphone should have these features, USA Today

My last MWC post inventoried six features that I think you’ll want on your next phone–and another that nobody should care about for a few more years.

2/27/2016: Emerging Multifamily Technologies Panel, NWP Energy Summit

The morning after I got home from Spain–professionalism!–I moderated this panel discussion with NWP’s Howard Behr, Greystar’s Pam Darmofalski, Embue’s Robert Cooper and Remotely’s Mike Branam about how smart-home technology is changing apartments.

Weekly output: CISA, e-mail “sub-addressing”

Greetings, frustrated owners of Timex sport watches. I’m glad that essay I wrote in a fit of nerd rage continues to draw such interest at each time change, and I hope that at least some of the people who come here looking for help taking their timepiece in and out of Daylight Saving Time stick around and keep reading.

I spent much of this week wrapping up work on a long and long-delayed story. This coming week will see me in Dublin, where I’m covering Web Summit and catching up with some cousins I haven’t seen in over a dozen years. That’ll be my last air travel for work this year, and I am quite okay with that fact.

Yahoo Tech CISA post10/27/2015: CISA: Why Tech Leaders Hate the Latest Cyber-Security Bill, Yahoo Tech

I had meant to write about this cybersecurity bill earlier, but instead this post went up on the day that the Senate approved it by a 74-21 vote. I guess the folks there did not find this piece terribly persuasive. FYI: If you don’t like rants about Obama’s creeping dictatorship, you might want to avoid the comments.

11/1/2015: When a site rejects email “sub-addressing”, USA Today

Want to protect your privacy by giving a site a custom e-mail address that still lands in your inbox? Some won’t let you do that, and their explanations don’t square with the basic specifications of e-mail.

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…