The longest running tool I have been using since the dawn of AI besides ChatGPT is Superwhisper. This is a program on iOS and macOS that transcribes your audio to text.
Why Superwhisper Became My Daily Driver
Let me tell you why this tool has stuck around in my workflow when so many others have come and gone. After years of struggling with Apple's built-in dictation - which somehow managed to be both inaccurate and oddly selective about where it would work - discovering Superwhisper was like finding the perfect pen after years of writing with crayons.
Universal Integration: It Just Works Everywhere
Superwhisper runs natively on macOS and integrates with the system clipboard, but here's what really sets it apart: it works in literally any app on your Mac. Unlike Apple's dictation that mysteriously refuses to activate in certain text fields or apps, Superwhisper treats every text input as fair game.
Whether I'm writing in Apple Mail, responding in Microsoft Teams, composing a quick text in the Messages app, or even filling out forms in my browser, I just hit my configured keyboard shortcut and start talking. The app sits quietly in your menu bar until you need it, then springs into action with a simple keystroke. I've set mine to Option+Space, and it's become as natural as breathing.
I love using the Push to Talk feature for mixing typing and talking.
The beauty is in the simplicity - there's no hunting through menus or wondering if this particular app supports dictation. It just works, period.
Custom Modes: Tailored for Every Context
This is where Superwhisper really shines compared to basic transcription tools. You can choose from built-in modes such as pure voice transcription, tailored text formatting, or create your own custom modes with personalized AI instructions.
I've set up different modes for different contexts:
Personal Email Mode: Automatically formats my rambling thoughts into professional, well-structured emails
Messages Mode: Voice only local model, and is on-device only.
Note Mode: Captures raw thoughts with minimal formatting
With Custom Mode, you can create specialized workflows by combining context-awareness with your own AI instructions. Want your voice notes to always come out as numbered lists? Done. Need every dictation formatted as a professional memo? Easy. The flexibility is genuinely impressive.
The app even includes auto-activation rules, so it can automatically switch to Email mode when I'm in Apple Mail, or Note mode when I'm in my note-taking app. It's like having an assistant who knows exactly what you need based on context.
Privacy-First: Local AI Models That Actually Work
All processing can be done on your device using local AI models. In an era where everything seems to require sending your data to the cloud, Superwhisper can keep transcription local.
You might think local processing means sacrificing quality, but the accuracy is genuinely impressive. The app incorporates advanced AI models—Nano, Fast, Pro, and Ultra—to deliver highly accurate transcriptions. I typically use the Ultra v3 model, which strikes a perfect balance between speed and accuracy.
Clipboard Context: The Secret Weapon
This feature alone has changed how I work with text. Super Mode intelligently adapts to your active applications, selected text, and clipboard content to deliver more accurate and relevant results.
Here's how I use it practically: Say I'm reading an email with a complex question, and I want to craft a thoughtful response. I'll copy the relevant part of their message, switch to Email mode, and start dictating my response. Superwhisper understands the context and formats my reply appropriately, often referencing the copied content intelligently.
Text copied to your clipboard will only be processed if done within 3 seconds of starting your dictation or while you're speaking, which prevents accidental context pollution while still giving you that smart contextual awareness when you need it.
It's particularly powerful for:
Responding to complex messages by referencing the original text
Editing documents where you want AI to understand what you're working on
Formatting text that you've already written but want to restructure
Custom Vocabulary: Teaching It Your Language
Every profession has its jargon, every person has their quirks, and Superwhisper gets this. The custom vocabulary feature lets you teach the app about your specific terminology, brand names, technical terms, or even the names of people you work with regularly.
As someone who writes about tech, I've added terms that are not transcribed correctly. Specific product names, and even abbreviations that I use frequently. The difference in accuracy is immediately noticeable - no more awkward auto-corrections of technical terms or having to manually fix proper nouns.
The Real-World Experience
After using Superwhisper daily for months, here's what I've learned: it's not just about the transcription accuracy (though that's excellent). It's about how it changes your relationship with text input entirely.
A Few Considerations
No tool is perfect, and Superwhisper has its quirks. Background noise can sometimes throw off transcription accuracy, so investing in a decent microphone or finding quiet spaces makes a difference. The experimental features are clearly marked as such - they're fun to play with but not always ready for prime time.
The Pro subscription starts at $8.49 per month or $84.99 per year when billed annually, though the free version allows up to 15 minutes of recording using all pro features, which is generous enough to really test the waters.
Other tools to look into
Microsoft Word
It would be irresponsible of me not to mention the product I work on at Microsoft!
Superwhisper inspired a feature we recently included in Microsoft Word for iOS. When I want to write a document in Word, I use this feature. You can read about it here. This is available for all Microsoft 365 Subscribers for personal use and our Copilot Subscription for Work. It’s a handy way to dictate documents on your phone.
Apple is also introducing a great offline transcription model in iOS 26, macOS 26. I’ve been testing it out with great success.
Wispr Flo
Wispr Flow is a dictation keyboard for iOS and it works great. Much better than the Superwhisper keyboard. No local model support but I like how simple it is.
Nice recommendation, Omar. Like that “Superwhisper treats every text input as fair game.” So frustrating when you hit a field that can be speech-to-text-filler-out. Will give it a try for sure. 👍