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Why Mac’s built-in Text Replacement isn't a perfect solution for text expansion?

The built-in Text Replacement on macOS is a simple and free text expander tool for automating your typing. But it falls short of being the best and most powerful auto-text software out there. Here’s why.
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For someone who writes for a living, I’ve been tempted to say this way too many times: “Alexa, will you write this blog for me?” only to have a “Sorry, I don’t understand” thrown in my face.

Make no mistake—I love writing. But there are certainly times when all that typing, especially repetitively churning out the same email copy or promotional message, gets to me. Typing all day long also puts me and others who do this often at a risk of repetitive strain injury that adversely affects tendons, nerves, and muscles in the hands, arms, wrists, shoulders, and neck. 

While voice typing or speech to text are viable options, I am not sure I want to talk to my laptop and hear only my own voice back for the better part of a day spent writing 5000 words. 

So what does one do? A simple solution is to use automation, specifically text replacement. 

What is text replacement? 

Text replacement, known by other terms such as text expansion or text substitution, involves replacing a long string of text with a shortcut or snippet. You can use the snippet to templatize frequently-used text and insert it automatically in your text editor (or other apps) with a few keystrokes. 

This has the obvious benefits of saving your time and energy and making you more productive, not to mention eliminating the frustration that comes with typing the same thing over and over like a pre-programmed machine. 

Recommended reading: How to boost productivity by using text expanders

How to start using text replacement?

Thanks to the many text expander tools available today, it has never been easier to get started.

In fact, if you’re working on a Mac and require basic text replacement, you might not even need to sign up and shell out money for any third-party tool. 

Built-in Text Replacement on macOS

With built-in Text Replacement, you can automatically replace text, symbols, and punctuation across a wide variety of macOS apps. For example, you can replace a double-space with a full stop and a space, brb with be right back, teh with the, double hyphens with em dashes (—), (c) with © etc. 

You can also convert URLs to clickable smart links.  

You can create and save text replacements easily by following two simple steps:

  1. On your Mac, head to the Apple menu  > System Preferences > Keyboard, then click Text. If you’re working in an app, you can also choose Edit > Substitutions > Show Substitutions, then click Text Preferences.
  1. Click the Add button in the lower left, then type the text to replace (such as teh) in the Replace column, and its replacement (such as the) in the With column.

Now, try typing teh in a text-editor such as a note-taking app and it should automatically get replaced with the.

As you might be able to guess, Mac’s built-in text expander is definitely not the fanciest or most comprehensive auto-text software out there. Yet, it has many merits.

Why use built-in Text Replacement on macOS?

So, why should you go for it over other tools? 

In the famous, if oft-misattributed words of the Everest mountaineer, George Leigh Mallory, “Because it’s there.”

No, really. If you’re already working on a Mac, you’ve got nothing to lose by trying it out. 

Here are some features that make built-in Text Replacement on Mac worth your while.

  • It’s free. You don’t have to pay a hefty license and/or maintenance fee to use it. Nor sign up for a SaaS subscription. 
  • It’s simple. The UI is as simple and intuitive as it can be. Plus there are thousands of tutorials and guides online teaching you how to make the best use of it. 
  • Works natively as well as on the browser. A lot of third-party tools may only work effectively on the browser with limited desktop support. This is especially true of extension based text expansion tools that don’t offer a desktop app. With the built-in text expander, you get the best of both worlds.
  • Syncs across iCloud. Want your snippets and shortcuts across all your Apple devices? Simply sync them to iCloud and use them on the go with your iPhone and iPad too. 

Great, right? Almost makes you want to give it a try right now! 

While the benefits look promising, they don’t completely make up for the limitations. 

And if you’re looking for a perfect productivity companion for your tired fingers, Mac’s built-in Text Replacement may not be it.

Why Mac’s built-in Text Replacement isn't perfect

I am guessing this text expander wasn’t built for what we’d call power users. 

The functionalities are inadequate for people who don’t just need to repeatedly type short phrases, numbers, addresses and the like every day, but those who send out the same cold email to hundreds if not thousands of prospects daily and those who have to rely on canned responses to solve the same support issues every five minutes.

Here are the top limitations of Mac’s built-in Text Replacement, which some of the available third-party tools can solve for good.

1. Doesn’t run on Windows

~76% of the world’s computers today still run on Microsoft Windows. While macOS has been steadily gaining in market share, it accounts for only ~15% of the machines worldwide as of June 2022. 

This excludes a lot of professionals from the purview of Mac’s built-in Text Replacement. It also paves the way for OS independent solutions such as browser extensions that can run on both kinds of machines or tools that offer custom apps for both the OS. 

Recommended reading: Top text expander apps for Windows

2. Doesn’t run on all apps

Built-in Text Replacements, smart quotes and dashes, and smart links aren’t available in all apps even on macOS itself. This is because it requires third-party developers to enable this feature from their end. 

A quick way to check if an app supports Text Replacement is to launch the app, go to Edit in the menu bar, and check if you can see ‘Substitutions’. If it’s present, the app is compatible with Text Replacement, otherwise not. 

Popular apps that don’t work with Text Replacement include Microsoft Word, Microsoft Outlook, and Mozilla Firefox. 

Browser based solutions also do not address this issue perfectly, but offer a wider scope of coverage, at least while you’re working within the browser.

3. Fails for longer pieces of text

As mentioned, power users might want to look elsewhere to replace long emails and canned responses with auto-text. 

One, you cannot directly type a snippet with multiple line breaks into the tool (though you can copy-paste a pre-formatted one). 

Two, you’ll almost always get a weird error message saying "The phrase must contain at least one character. Please provide a valid word or phrase”, when you try to paste a substantially long text into the With column. 

The solution? You can break the text into two snippets. However, it’s not foolproof and can be pretty annoying when you have hundreds of snippets to deal with. 

4. Triggers accidentally if not careful 

If you’ve a snippet set to trigger with a word you use frequently otherwise too, there are high chances of text replacement being triggered without you intending to. 

For example, if your cold sales pitch is replaced with the shortcut ‘sales’, every time you use the word sales in communication, it will be substituted with your pitch instead.

This is why you’ll need to add a distinct, intentional prefix to demarcate the snippet from the word itself, something like /sales or ;sales, for instance. 

Third-party tools solve for this automatically by having a special prefix built-in for triggering the snippet.

Pro tip: Letters are better than special characters when choosing a prefix, especially if you do a lot of text replacement on your iPhone/iPad. With a letter as prefix, you’ll not need to switch the keyboard to trigger the snippet which is more efficient. 

5. Makes exporting snippets complicated 

If you’re switching Mac devices, you’ll need to manually export all the snippets from one computer to the other. You can do this by dragging your snippets to the Desktop to create a Text Substitutions.plist file with them saved in it. You can then drag and drop this file into the Text Replacement field on the other machine, in order to import your snippets.

Most third-party solutions offer cloud storage that automatically syncs your snippets across devices where you want to access them, without resorting to manual exports. It’s much easier, faster, and more convenient.

So, which third-party text expander should you go for if you are dissatisfied with built-in Text Replacement?

OSlash—the text expander for all use-cases

Whether you’re a power user or just need a simple text expander that works across all your apps, natively, as well as on the browser, OSlash has got you covered. 

It is a versatile productivity tool capable of serving multiple use-cases. Whether you want to send personalized outreach email blasts to potential hires, help your customer support reps with consistent canned responses, create quick replies for social media mentions, or templatize follow-up emails for your sales reps, OSlash can help.

With OSlash text expander, You will be able to save close to 30 hours a month by automating your most-used snippets, formatting them to look beautiful, and inserting variables in highly personalized messages. 

You will be able to create snippets for your team, your workplace, or just for yourself. Additionally, you can also highlight anything on the web, right-click and convert it into a snippet. 

The best part? OSlash also helps you transform your most frequented pages/links into simple shortcuts such as o/daily-standup or o/q1-priorities. So that you can find, access, and share information blazingly fast. It is the best tool to streamline your workflows and be more productive.

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