There are more dictation apps for Mac than there were two years ago, and most of them look the same in a screenshot: a microphone icon, a menu bar, a promise about accuracy. The differences show up after a week of use. These are the five that matter.
1. Does it type into every app?
The point of dictation software is to replace the keyboard, so it has to work wherever the keyboard works: Mail, Slack, Word, Google Docs, Notion, a browser, a terminal. An app with its own window that you copy from is a transcription tool, not a dictation app.
2. Transcript or finished text?
Say “um can you, uh, send the deck, no, the new deck, by Thursday”. A transcript gives you that. A good dictation app gives you “Can you send the new deck by Thursday?” This is the difference between saving time and moving it.
3. How does it start and stop?
Hold-to-talk (hold a key, let go when done) beats a toggle for almost everyone, because you can’t forget to stop. Why hold-to-talk wins.
4. Can you teach it your words?
Names, products, jargon. A vocabulary list you control is what makes the last 2% of words right, and that 2% is the words that matter. Custom vocabulary explained.
5. What does it do in AI apps?
More typing goes into Claude, ChatGPT and Cursor every month. A dictation app that knows a prompt has a different shape to a message saves you the follow-up questions. Only a couple do this.
The options on a Mac
Speaky Box. Every app, finished text, hold-to-talk with two keys you choose, vocabulary, and a Smart key that writes a structured prompt in AI apps and an email in Mail. Free for 2,000 words a week, £8.99 a month unlimited. Mac only. Ours.
Wispr Flow. Every app, clean text, hold-to-talk, cross-platform with a meeting notetaker. $12 to $15 a month. Comparison.
Superwhisper. Local models, offline, configure your own modes. Comparison.
Lemon. Voice to prompt for AI tools, dictation elsewhere, Mac and Windows. Comparison.
macOS Dictation. Free, built in, transcript only. Comparison.
Every one has a free tier or trial. Pick two, dictate the same three sentences into each, and you’ll know.