Dictation on a Mac used to mean saying “comma” out loud and fixing the result afterwards. That changed when large speech models got fast enough to run in the time it takes to lift your finger off a key. Now the question isn’t whether to dictate, it’s which app to do it with.
This is a practical comparison of the five you’re likely to be choosing between. We make one of them, so read the Speaky Box parts with that in mind. The rest is as fair as we can make it.
What actually matters
Four things separate a dictation app you’ll use every day from one you’ll try once.
Cleanup. A literal transcript of how people talk is unusable. You want the ums, the restarts and the “no, wait” removed, and the grammar fixed, without your meaning changing.
Where it works. It should type wherever your cursor is, in every app, with no plugins. If it only works in its own window you’ll stop using it in a week.
What it does in AI apps. More and more of what people type goes into Claude, ChatGPT and Cursor. A prompt has a different shape to a message. The good apps know the difference.
Price and privacy. What the free tier covers, what the paid tier costs, and where your words end up.
Built-in Mac dictation
Free, already installed, and fine for a sentence here and there. The transcript is literal (ums included), you punctuate by voice, and it produces the same output whether you’re in Notes or in a prompt box. Recognition on names and technical terms is the weakest of the group. If you dictate rarely, stop reading and use this.
Wispr Flow
The most established option, and the only one here on Mac, Windows, iPhone and Android. Hold a key, talk, and clean text lands where your cursor is. It adds a meeting notetaker and team plans, which tells you who it’s for: teams who want one tool across every device. The free tier has weekly limits; Pro is $12 a month billed yearly or $15 monthly at the time of writing. It cleans up what you said but doesn’t restructure it into a prompt.
Lemon
Lemon started from the AI side: its pitch is voice to prompt. Ramble at it in Claude or ChatGPT and it produces a structured prompt. It also has a dictation mode for everything else. Mac and Windows. Pricing is on their site. If prompting is the only thing you dictate, it’s a strong choice.
Superwhisper
The tinkerer’s pick. Runs models locally on your Mac, which means it works offline and nothing leaves your machine. You can write your own modes and prompts for different apps. The trade-off is setup: you’re choosing models and writing prompts yourself, and quality depends on the model you pick.
Speaky Box
Ours. Two keys: Dictate gives you your words, tidied, in any app. Smart knows which app is in front and writes for it: a structured prompt in Claude, ChatGPT and Cursor, an email in Mail, a message in Slack. Mac only. Free for 2,000 words a week with both keys and no card; Pro is £8.99 a month for unlimited words. History stays on your Mac and can be switched off.
The short version
| If you… | Use |
|---|---|
| Dictate occasionally and don’t mind tidying up | Built-in Mac dictation |
| Need Windows or your phone, or want meeting notes | Wispr Flow |
| Want everything local and like configuring things | Superwhisper |
| Mostly write prompts for AI tools | Lemon or Speaky Box |
| Want one app that’s as good in Mail as in Claude, on a Mac, at a low price | Speaky Box |
Whichever you pick, the habit is the same: hold the key, say it how you’d say it, let go. Once it clicks you’ll wonder why you ever typed a Slack message.