Adios, TextExpander

Smile’s latest “upgrade” feels more like extortion.

Sean Conley
The Reasonable Person
5 min readApr 6, 2016

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TextExpander 6, by Smile Software.

Using a text expansion tool for the first time feels as close to magic as one can get after decades of familiarity with modern technology. At its most basic level, this type of software lets one type something like “#name”, which the app then automatically expands to “John Q. Public”. For years, the best-in-class text expansion software has been TextExpander by Smile Software. Today, Smile announced TextExpander 6, along with the news that the software is now a subscription product. This is a colossal misstep by Smile, and it’s going to cost them droves of users (including me).

Text expansion has been around for decades. It’s one of those things you won’t really understand, or see the charm of, until you try it yourself. In my law practice, for example, I frequently use phrases like “Parent of Primary Residence (PPR)” and “Parent of Alternate Residence (PAR)”. Of course, I can always type those phrases out each time I need them. But as we all do with repetitive, monotonous tasks, I longed for a better way.

With TextExpander, I simply type #PPR (my chosen “snippet”), and the app saves me the two seconds I’d waste banging out the other 30 or so characters. Those few seconds, when combined with countless others, actually do add up to meaningful amounts of time (which TextExpander helpfully documents for you in case you’re curious). Users have been able to sync their TextExpander snippets between computers and mobile devices for free using Dropbox, so that they are never without a text expansion option.

Until now, TextExpander has always been sold as a traditional software product. Every year or two, Smile releases a new version and charges for it. You buy your upgrade and use it for as long as you like. With version six, however, Smile has switched TextExpander to a subscription model. Individual users must pay $48-$60 per year in order to continue using the software and syncing their snippets across devices. Smile has also introduced a number of features designed to appeal to — and a new pricing tier aimed at — businesses, including shared snippet snycing between teams.

I purchased TextExpander years ago, and have paid for upgrades to it more than once. I did so gladly because I saw concrete gains from using the software, and I wanted to support its development. That ends with this new version. Smile’s decision to begin charging for syncing, a feature that has been free until now, is monumentally foolish. Rather than add something meaningful in a paid upgrade, they have removed a key feature only to resurrect it with an unnecessary recurring cost. Perhaps for new users that never knew free syncing this won’t be too disagreeable, but it feels like a giant middle finger to existing customers.

The first tweets I’m seeing on this upgrade are as harshly negative as my initial reaction. Users feel as if their longtime loyalty is being repaid with an extortative demand for recurring payments in exchange for previously-free functionality. Virtually all commenters also appear to agree that the price is far too high without features to justify it. These are fair criticisms, and Smile should have foreseen this reaction from their user base. If they did not, they understand little about their customers and the software market generally.

I suspect, however, that they knew exactly what they were doing. This move reeks of desperation; a Hail Mary to save a company not doing well enough in a competitive marketplace. They simultaneously shed individual buyers, the margins on whom are not high enough, and attempt to attract business users, who are more than willing to pay subscriptions for productivity apps. Of course, doing so means sticking it to their most loyal customers, but hey, it’s just business, right?

Maybe Smile will be able to generate revenue by refocusing the product on enterprises. But no sane individual users will pay the prices they are demanding just for the privilege of keeping the functionality we already have. For my part, I’m switching to the text expansion option built into Mac OS X (Apple > System Preferences > Keyboard > Text). It syncs through iCloud, so I can use my snippets on my iPhone and iPad as well. And it’s free. If you go this route, once you set up your text shortcuts, open Terminal and run the following command:

Per this Macworld article, that command will enable text shortcuts in all apps that support them.

If you want an easier but not free option, check out aText; it’s a one-time payment of $4.99. That’s something like one-seventh of what Smile was charging for TextExpander, and less than a tenth what they want for a year of their new service.

Software developers should take heed of the lessons demonstrated by Smile in this case. Don’t force your users to buy yet another subscription when your product’s purpose doesn’t call for one. And remember that upgrades need to offer value. Taking away existing features only to charge for them later is extortion, plain and simple. Users will recognize these types of transparent money grabs and punish you for them.

My guess is that there won’t be too many happy faces over at Smile today. But as one of many longtime users of a once-great product who have now been tossed by the wayside, I can’t say I feel bad for them.

Update (April 12, 2016)

Smile has apparently heard our feedback and changed course. Per this post on their blog, they are adjusting pricing such that existing users will pay $20/year in perpetuity. This brings the price back down in line with what they were charging for yearly upgrades before implementing the subscription model.

I appreciate that they heard their customers’ complaints and took them to heart, and I will seriously consider signing up for a subscription at the reduced rate. But the fact that they had to go through this rigmarole in the first place certainly doesn’t speak well to their business sense. Any rational person should have foreseen that a 300% price increase wasn’t going to go over well with loyal customers.

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