Rememeber Dragon Dictate – What happened to Voice Dictation?

From Audrey to AI: The Evolution of Voice-to-Text

It’s funny to think about, but talking to your computer has been around longer than the home computer itself. What started as clunky experiments with machines that could barely understand numbers has now become everyday productivity. These days, you can open your laptop, phone, or a tool like Typeless, start speaking, and watch your words appear instantly with near-perfect accuracy. Let’s take a quick journey through the history of voice-to-text and see how far we’ve come.

Voice-to-Text Timeline

The Early Days: Machines That Could Count

Back in 1952, Bell Labs built Audrey, a system that could recognise digits from zero to nine. Not exactly poetry, but it was groundbreaking at the time. IBM followed in the 60s with its Shoebox, which managed 16 words and wowed crowds at the World’s Fair. Government research in the 70s pushed things further, with DARPA funding systems that could recognise about a thousand words. Still, all of this was experimental, locked away in labs, far from everyday use.

The 80s and 90s: From Labs to Living Rooms

The 80s saw bigger vocabularies and the first real attempts at commercial use, with Kurzweil Speech Recognition leading the charge. But the big breakthrough came in the 90s. DragonDictate arrived in 1990 for Windows PCs — the first consumer-ready software that let you dictate text. It wasn’t perfect, and it needed lots of training, but professionals like doctors and lawyers started to use it.

IBM jumped in with ViaVoice in 1997, bringing competition and eventually support for Mac users. But in those days, Windows had the stronger software while Mac users lagged behind with limited tools.

The 2000s: Accuracy Gets Serious

By the early 2000s, Dragon NaturallySpeaking had become the gold standard, hitting around 95% accuracy if you were patient enough to train it. For the first time, voice dictation became practical for writers, journalists, and anyone with accessibility needs. Windows XP shipped with basic speech recognition, making it mainstream, while Mac users got iListen and later MacSpeech Dictate, though they were still a step behind until Nuance (the makers of Dragon) finally brought their software over.

The 2010s: Cloud and Smartphones Change Everything

Then came the real game-changer — smartphones and cloud computing. Apple Siri launched in 2011, followed quickly by Google Voice on Android. Suddenly, millions of people were talking to their devices, not just for dictation but for commands, search, and messaging.

Transcription tools like Otter.ai, Rev, and Trint made it possible to turn meetings, lectures, and interviews into text automatically. Dragon Dictate for Mac finally gave Mac users the same power PC users had enjoyed for years. Voice-to-text went from a niche professional tool to something anyone could use.

The 2020s: AI Delivers on the Promise

Fast forward to now, and we’re in the golden age of voice-to-text. AI-powered models like OpenAI’s Whisper, Google’s speech-to-text API, and Microsoft’s Azure Speech have pushed accuracy and speed to levels we used to only dream about. The clunky training days are over — these tools adapt instantly, even to different accents and noisy environments.

On the productivity side, tools like Descript and Otter.ai don’t just transcribe — they summarise, edit, and make your spoken content searchable. And then there’s Typeless, a beautifully simple app that lets you use your voice as your keyboard. No setup, no heavy software, just open it and speak. For anyone who writes a lot, it’s a massive time-saver.

PC vs Mac Today: No More Gaps

For decades, PC users had the edge in voice-to-text, but that gap has finally closed.

• Windows 11 comes with Voice Typing powered by Microsoft’s AI — smooth, accurate, and deeply integrated with Office and Teams.
• macOS Ventura and Sonoma (OS 26 included) offer Enhanced Dictation, which is fast, accurate, and works offline for short bursts.

Both platforms now have excellent built-in tools, but the real magic comes from layering on AI-driven apps like Typeless, Whisper, or Otter. These take the native dictation experience and turn it into a genuine productivity booster.

The Bottom Line

From a clunky machine in the 1950s that could only count, to today’s AI assistants that can transcribe your meetings, write your emails, or even type out an entire book for you — voice-to-text has come a long way. For the first time, it feels like the technology is finally keeping up with the dream: speaking naturally and seeing perfect text appear.

With today’s tools, especially Typeless and AI transcription platforms, writing has never been easier. The future of typing? It’s sounding more and more like talking.

Voice-to-Text Timeline