TextExpander and App Rental

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I dislike wading into battles of opinion. While I may be cranky, I’m not all that self-important. But I’ve recommended the Mac and iOS app TextExpander many, many times and feel like I’ve endorsed it enough that I now have an obligation to all the people that listened to me, even if I don’t want it.

I recommend Dr. Drang’s post and the latest Back to Work episode for additional opinions from similarly invested nerds. This post at Practically Effecient considers why we pay for software at all. Michael Tsai has a tremendous round up of opinions.

Everyone has an opinion. Here’s mine. It’s long.

I’ve been an ardent fan of TextExpander (TE) for as long as I can remember. Even when the more powerful Keyboard Maestro added typed-text triggers, I stuck by TE because I liked how it worked. I liked that it could sync with iOS. I also like Smile Software. Each year, the iOS version felt more neglected but the integration with other apps was incredible. The TE keyboard on iOS was the only one I trusted to give “full access.” Even though the iOS keyboard always felt slow and outdated I still loved the app for its syncing and integration across all the apps I used.1

Smile has a new business model for TextExpander 6. They call it a subscription model but I’m going to call it app renting. I think of a subscription as a recurring fee for ownership. When I rent, I get an access and usage permission but I get nothing to keep. It’s pedantic and probably wrong but it’s how my mind keeps track of value. They can call it what they want and I can call it what I want. We’re good.2

A Few Words About Money, Charity, and Support

I buy every version of most of my currently installed software. If it’s still installed when an upgrade comes out, then I buy it. This means I buy a lot of software. I buy almost every app I have ever reviewed on this site. I buy multiple copies when it’s convenient. I bought the last TextExpander upgrade sight unseen just a year ago. I’d happily buy another version now for full price. This is not normal. Most “normies” don’t want to pay for software even once, let alone pay for updates. The mainstream market will pay for jewels and tokens before they buy an app upgrade. It’s a difficult market and an upgrade needs to be amazing but will still get slammed in reviews. That’s just the way it is.

I do not buy software out of charity but I do pay for software out of fairness. There are plenty of really excellent charities in the world that do a lot of good with a dollar. I disagree with most arguments about supporting developers. If you want to insure the continued existence of a particular piece of software then it’s much better to advertise for them. Recommend the app. Rate the app. Write into blogs and tell them how great it is. Charity app-buying does not seem like a sustainable model but I’m probably a bad person.

I’ve also accepted that things cost different amounts than I am accustom to. I now pay $20 for a digital copy of a movie and $10 for delivery of a physical copy of the same movie. A cup of coffee is $3. A smaller cup of coffee is $4. I don’t understand markets but I do understand value. The TextExpander service, the YNAB service, and even the new Day One are not a value to me. I get very little in return for what I consider to be a high cost.


My real issue with the new TextExpander is similar to my issue with YNAB and Day One.3 The requirement for syncing through their service does not fit my needs. My snippets are mostly dumb but not entirely benign. I have addresses, phone numbers, names, and server connection strings. Risk of trusting amateurs is not worth the returned value of convenience.

When it comes down to it, I just don’t trust every developer to be good at securing my data even if I like their apps. I look at their software and the bugs I stumble over, then I think about what that means for their back-end design. I wonder how they document their security roles and what their schedule is for a pen-test. How is the data treated at rest? Who has access to the database or even the connection details? When was the last time they were audited by a third party? These are things I don’t want to think about when I create a text snippet.

An obvious question is: Do I trust Dropbox. I trust Dropbox to be good at security control and server administration because that is their primary job. I do not trust them to guard against government intrusion or dumb acquisitions. In the end, I do trust Dropbox, Box.net, Google, and even Microsoft to have a security team with experience. I trust that they have experience securing data against accidents and malfeasance. I trust that they know what they are doing.


I have no high ground. It’s not my place to say what is a good business decision for someone else. Smile wants recurring payments and their own syncing service. That’s cool. I don’t want that so we no longer have anything in common. I got what I paid for up to this point. This is the end of my noodling with and recommending TextExpander. I’m bummed out that I have to use my time to review and migrate all of my snippets. I’m disappointed that I’m losing an app I liked but I’m not short on options.

Smile says they will support TextExpander up through the next major OS X version. That’s great because it gives a lot of people I know time to move their snippets to another system. I’m inclined to heed the first warning shot.

Sifting Through Commodities

I don’t have a need for team management of snippets. If I did, maybe this would be a good option. Dropbox is also a good way to work with a team. For a standalone user I have many options for a replacement. Nothing is exactly like TextExpander but in some areas that’s good.

On the Mac and iOS TypeIt4Me works. It’s not as good as TE but it does a lot of what most people need. (UPDATE: TypeIt4Me can also import TE snippets. I just recreated them instead) Typinator is made by Ergonis which is a reliable longtime Mac developer. Alfred is just fine for basic snippets on the Mac but aText is probably the better option if you don’t like TypeIt4Me or Typinator.

Keyboard Maestro is far more powerful than TextExpander on the Mac but lacks any useful functionality on iOS. It’s also more difficult to wrangle for some people. For me, Keyboard Maestro is a major step up from TextExpander and I’ll make the transition with ease.

On iOS I use Drafts a lot and already had issues with TextExpander integration. I created many of my common snippets right in Drafts and it’s much faster and easier. I also use Editorial and prefer the native snippets over TextExpander integration. Access to the full Python features of Editorial from within a snippet is incredible.

I’ve actually moved a lot of my common snippets to the Copied app for Mac and iOS. It syncs through iCloud and has a nice keyboard on iOS. The search function makes it pretty great and I don’t need to remember a bunch of keyboard shortcuts.

On Windows, AutoHotKey is far beyond TextExpander on the Mac. It’s not for the faint hearted and it doesn’t sync with any of my Mac or iOS applications. I love the AutoHotKey format because it’s based on plain text scripts but it’s not an easy road to travel. I’ve mostly created the snippets I need already. I don’t miss syncing there. If you do want syncing Breevy is a good option but AutoHotKey is much more powerful.


So there it is. You skimmed to the bottom to find out what are good replacements. On Mac I think Keyboard Maestro is an upgrade for me and most other people. On iOS I’ve switched to a combination of the built-in iOS text expansions and snippets in Drafts and Editorial. On Windows AutoHotKey is impressive. There are plenty of options on every platform, which is what makes this move by Smile so bewildering. Luckily I don’t need to understand their business. I just need to save a few keystrokes so I have time to write blog posts about automation.

TypeIt4Me | Mac | $20

TypeIt4Me | iOS | $5

aText | Mac | $5

Alfred | Mac | $19

Keyboard Maestro | Mac | $36

Typinator | Mac | $28

Copied | iOS | Free

Copied | Mac | $8

AutoHotKey | Windows | Free

Breevy | Windows | $35

  1. The version 6 keyboard still lacks long-press to change keyboards. (UPDATE: as wisely noted on Twitter, this is probably true for all third party keyboards) ↩︎

  2. Sure, Netflix calls it a subscription too. I get it. There’s no need to send me examples. I conciously consider Netflix, my cable box, and Apple Music all rental services. If I don’t pay them then they take their ball and go home. Amazon Prime is a subscription service that saves me money for shipping and then gives me movies and music for free. The internet is weird. ↩︎

  3. It’s actually a huge bummer for me with Day One because I’ve used that app for years. Luckily, one of the reasons I used it was that I could get my data out when I wanted to. I miss it but I’ll live. ↩︎