If you dictate on your Mac every day, choosing between Dictato and Typeless is not about which one hears you better. It comes down to where your voice is processed, what you pay over the years, and how much rewriting you want.
What Typeless does well
Typeless runs on macOS, Windows, iOS and Android, the widest reach in the category, and promises a consistent experience across them. If you dictate on a phone as much as a laptop, that alone can settle it. The free tier is real too: $0 for 8,000 words a week at standard accuracy, while Pro adds unlimited words, enhanced accuracy and priority access. Its headline feature, AI rewriting, is well liked: it removes filler words and repeated words, spots mid-sentence self-corrections and keeps only your final intent, and formats spoken lists. It claims 100+ languages with auto-detection, plus translation, a personal dictionary, different tones per app, and an explicit zero-retention, no-training policy.
Dictato is macOS only, and needs macOS 14 or later on an Apple Silicon Mac. If Windows or Android is part of your day, stop reading here.
Where your audio goes
The Typeless privacy policy (updated March 13, 2026) states that audio is processed in real time on their cloud servers and discarded once the transcription comes back. Their phrase “on-device history storage” describes where history is kept, not where audio is handled, and no offline mode is documented on their site. An account is required, with sign-in by Google, Apple, email or SSO.
With Dictato, audio and text never leave your Mac, and it works offline after a one-time model download. The only network traffic is a license check, a trial check and update checks. Anonymous usage stats are opt-in, off by default, and stop once you buy. No account, no email. Here is why that matters.
What it costs over time
Typeless Pro is $30 a month, or $12 a month billed yearly, so $144 prepaid per year, per member, for as long as you use it. Dictato is 19.99 EUR once, lifetime, after a 7-day trial with no card. But if 8,000 words a week covers your writing, the free tier costs nothing. The real cost of speech to text walks through the arithmetic.
Rewriting versus formatting that never varies
Both sides trade something here. Typeless bets on AI rewriting, which pays off when your speech rambles or restarts. Dictato bets on rules: numbers, dates, currency amounts, ordinals and phone numbers come out written correctly with nothing to configure, identically every time, because that layer runs last. That matters when an invoice number has to be exact. See how it handles numbers and dates.
Two limits, stated plainly. That formatting covers English and French only, while dictation covers 30 languages and cleanup covers 10. And punctuation, capitalization and paragraphs are not automatic: you switch on auto-correct or set a per-app profile, and a small local model adds them. The upside is that what you said is what you get by default, with no rewriting layer in between. Hesitation sounds and stuttered words are always removed, but words like “like” or “you know” are left alone.
Which one to pick
Pick Typeless if you dictate across several devices, want speech cleaned up aggressively with no setup, or want a free tier.
Pick Dictato if you are Mac-only, want nothing sent to a server, prefer paying once, and need numbers and dates right every single time.