Smile History: TextExpander, a Story of Change, and Typing

12 Years of TextExpander

On June 12, 2018, Smile celebrates our 15th birthday. In this series we’re looking back at some of our history. Hope you enjoy!

TextExpander was Smile’s first acquisition. Originally called Textpander, it was developed by Peter Maurer, now of Many Tricks. Smile shipped TextExpander 1.3 on May 23, 2006. Our original blog post does a good job of telling the origin story.

One of the instigating factors of producing TextExpander was, in fact, our need of it, similar to PDFpen. We were a very small team at that time, and having to be full time developers and full time suport and run a company was challenging. One of the ways we found to help was through the use of a text expansion tool. But, that app’s updates weren’t reliable, so we decided if we were going to have an app that our company needed, we could make it ourselves.

TextExpander 2.0, released in October 2007, began to flesh out the product, adding: snippet groups, group import, hotkeys, printing, AppleScript snippets, and MobileMe 😱 sync. Check it out in all of its stripey, System Preference pane glory, and note the example email address from

TextExpander 2 Screen Shot
TextExpander 2.0

TextExpander for iPhone / iOS SDK

At WWDC in 2009, Apple announced support for cut/copy/paste in iOS 3. At our WWDC Smile party, Dave and Roustem from AgileBits, makers of 1Password, told us that if we did not produce TextExpander for iPhone, they would. I wasn’t entirely sure they were joking, so we got on it. We built TextExpander for iPhone, which debuted on August 26, 2009. Initially, it could only expand snippets in the Notes section of the app.

One of the greatest side effects to our acquisition of TextExpander is that I became good friends with Peter Maurer. He attended WWDC 2009 and stayed at our house. On one of our BART rides into San Francisco, Peter suggested developing an SDK so that third party apps could add support for TextExpander directly in their apps. Today, some of the best productivity apps for iOS, including OmniFocus, Drafts, and Bear, include native support for TextExpander.

The real game-changer on iOS was when Apple introduced custom keyboards in iOS 8. Now, we’re able to make basic TextExpander expansion available in any app.

Evolution of the TextExpander Icon
Evolution of the TextExpander icon

TextExpander Application

Version 3, released in March 2010, marked TextExpander’s escape from the confines of System Preferences into a full-fledged application. We introduced single line fill-ins, Dropbox sync, capitalization correction, and hotkeys to create new snippets and to edit the last expanded snippet.

TextExpander 4.0, released in June 2012, focused on enhanced fill-in support. We introduced three new types: multi-line text fields, popup menus, and optional text sections. We added default values for fill-ins, the ability to expand snippets when filling a fill-in, and the ability to switch apps while filling a fill-in. We also retired MobileMe sync, as Apple retired the MobileMe service.

Version 5, released in May 2015, added suggestions as well as sync support for iCloud Drive. We added support for cross-platform JavaScript snippets. Fill-in fields could be instructed to appear at the top of the fill-in window to make filling lengthy snippets easier. We also added snippet preview and improved the presentation of statistics.

TextExpander in the Cloud

Shortly after we shipped TextExpander 3, we identified sharing as a feature which we believed would make TextExpander more powerful. We had mixed experience with leveraging sharing and sync systems from others, including MobileMe, Dropbox, and iCloud Drive. Eventually, we realized we needed to move TextExpander’s storage to our own cloud so that we could offer robust support for entire teams sharing snippets with one another.

The TextExpander team met in Portland in April 2015 to plan out our new TextExpander service. We rolled out to beta users on October 12, 2015. Fittingly, our friends at AgileBits were among our first beta customers.

We launched the complete TextExpander service on April 5, 2016. We fumbled a bit on the pricing, and there was controversy around subscriptions, which caused us a few sleepless nights and seems quaint in retrospect. We made some adjustments to serve our customers better. Public groups debuted, complete with an option for folks to publish their own groups. TextExpander customers began sharing snippet groups for the first time ever, and productivity improved once again.

TextExpander on Windows

We built a Windows client to broaden our offering and serve customers who’d been asking for this for a long time. We started with a “headless” client which could only sign in to TextExpander, download snippets, and handle expansion. Users with Mac and Windows machines could finally use TextExpander on both. In January 2017, we shipped TextExpander for Windows 1.0 with a complete user interface for viewing and editing snippets.

TextExpander for Windows
TextExpander for Windows

TextExpander Today

Today, we have teams with over 1,000 users on TextExpander, saving 4-8 hours per month per user. We have individuals using TextExpander on Macs, iPads, iPhones, and Windows machines, with immediate access to all of their snippets on all of their devices. It’s amazing to think that fewer than nine years ago, TextExpander was a Mac-only System Preferences pane. We’re excited at how far we’ve come with TextExpander, and we’re looking forward to a bright and active future.


Smile Founder
Casual Typist Champion