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Tracked since2026
The Bottom Line
Entry price
Free, no paid tier
Biggest pro
Saves time by preparing replies with relevant context from calendar and past commitments
Biggest con
Limited to one-to-one Messages conversations for reply preparation
TL;DR - Chalked for Mac
- Reads one-to-one Messages conversations and prepares replies grounded in your calendar and captured commitments.
- Insert suggestions with Tab or dictate custom replies with the fn key; nothing sends automatically.
- Captures commitments with source and status, keeping memory inspectable and editable.
Pricing: Free forever
Best for: Individuals & startups
What is Chalked for Mac?
Chalked is a Mac app that reads your one-to-one iMessage conversations and prepares context-aware replies using your calendar and working context. It captures commitments from messages, keeps them inspectable with source and status, and allows you to insert a suggested reply with Tab or dictate a custom one with the fn key. The app runs locally on Apple Silicon Macs with a recent macOS version and advanced AI capabilities, using Accessibility to read the current window without screenshots or screen recording. It is designed for professionals who need to respond quickly while keeping track of promises and deadlines, such as agency operators, consultants, and founders. Chalked works in Messages and offers global fn dictation in other Mac apps.
Pros & Cons
Pros
- Saves time by preparing replies with relevant context from calendar and past commitments
- Privacy-focused: no screenshots, no screen recording, and text stays on your device
- Captures commitments automatically, reducing the risk of forgetting promises
Cons
- Limited to one-to-one Messages conversations for reply preparation
- Requires a recent macOS version, Apple Silicon, and advanced AI capabilities, restricting compatibility
Key Features
Reads current iMessage conversation through Accessibility to prepare context-aware repliesIntegrates with your calendar to ground replies in schedule and availabilityCaptures commitments from messages with source, status, and ability to supersede old entriesInsert suggested reply at cursor with Tab keyHold fn key to dictate a custom reply or modify the suggestionGlobal fn dictation works in any Mac app, not just MessagesNo screenshots or screen recording; on-screen text stays on your MacMemory is inspectable: view, correct, export, or remove captured commitments
Pricing
Free
Chalked for Mac is completely free to use with no hidden costs.
Reviews
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Chalked for Mac FAQ
How does Chalked help professionals manage commitments made in iMessage?
Chalked automatically captures commitments from your one-to-one iMessage conversations and keeps them inspectable with the original source and status. This reduces the risk of forgetting promises and deadlines, making it especially useful for agency operators, consultants, and founders who need to track follow-ups.
How does Chalked differ from Flowrite in its approach to privacy?
Chalked uses Accessibility to read the current window without screenshots or screen recording, and all text stays on your device. This privacy-focused approach contrasts with cloud-based tools like Flowrite, which may process text externally. Chalked runs locally on Apple Silicon Macs, keeping your data on-device.
What kind of conversations does Chalked support for reply preparation?
Chalked is limited to one-to-one Messages conversations for reply preparation. It does not support group chats or other messaging platforms for this feature, so users who primarily communicate in groups may need to consider that limitation.
Which teams benefit most from using Chalked?
Professionals who need to respond quickly while keeping track of promises and deadlines, such as agency operators, consultants, and founders, get the most value from Chalked. The app is designed for individuals who handle high volumes of iMessage conversations and want context-aware replies without losing track of commitments.
How is Chalked priced?
Chalked is free to use and does not require a paid plan. There are no subscription fees or hidden costs for accessing its features, including commitment tracking and context-aware reply drafting.
How does Chalked capture commitments from messages?
Chalked reads your one-to-one iMessage conversations and automatically identifies commitments, keeping them inspectable with the original source and a status indicator. Users can track these promises directly within the app, reducing the risk of forgetting important follow-ups.
Does Chalked work outside of the Messages app?
Chalked works in the Messages app for reply preparation and commitment capture, and it also offers global fn dictation in other Mac apps. This allows you to dictate custom replies using the fn key across different applications, though the context-aware reply feature is limited to iMessage.
How does Chalked read the current iMessage window without screenshots?
Chalked uses Accessibility permissions to read the text of the current iMessage window directly, without taking screenshots or recording the screen. This approach ensures privacy by keeping all data processing on your device and avoiding any visual capture of your screen.
Source: usechalked.com