Conversation-grounded replies
Chalked starts with the thread you are currently replying to and prepares a complete response using relevant conversation details rather than asking you to reconstruct the context elsewhere.
Chalked
Freemium
Chalked is a Mac reply assistant that reads the conversation you are in and prepares context-grounded responses for Gmail, LinkedIn, and, on macOS 26, Messages. It uses calendar and working context when relevant, while leaving review, editing, and sending to you.
What is Chalked?
Chalked is a reply assistant for Mac that prepares context-grounded responses inside the conversations where work already happens. It reads the current thread and can use relevant calendar and working context to suggest a reply. Prepared replies currently work in Gmail and LinkedIn in Safari or Chrome, while English Messages support is available on macOS 26.
The product is designed as a review-first workflow. A prepared reply can appear at the edge of the notch or at the cursor; pressing Tab inserts it into the verified composer. Holding fn lets you dictate a different intended outcome. Chalked does not send messages automatically, so you decide whether to edit, ignore, or send the inserted text.
What can Chalked do?
Calendar and working context
When it matters to the reply, Chalked can use calendar information and working context to ground details such as timing, commitments, and dependencies.
Tab-to-insert workflow
When a prepared reply is ready, press Tab to insert it at the cursor in the same verified composer. The text remains available for review and editing before you send it.
Voice-directed changes
Hold the fn key to dictate what you want instead of accepting the prepared reply. This can be used to change an outcome, such as adjusting a proposed time or preserving a stated budget limit.
Sourced commitment memory
Captured commitments retain their source and status. You can inspect, correct, export, or remove them, and changed commitments can supersede older entries instead of leaving both marked current.
Bounded context and private mode
The product says it reads a bounded current conversation through Accessibility, without screenshots or screen recording. Private mode keeps reply context on the Mac; Best Quality shares the disclosed bounded packet only after you enable it.
Use Cases
“Confirming client delivery details”
An agency operator can reply to a client about timing, budget, and approval dependencies while keeping the commitments that shape the work explicit and sourced.
“Returning to a consulting engagement”
A consultant can use retained, inspectable context when responding to a client days after the earlier conversation, rather than rebuilding the engagement from memory.
“Moving between stakeholder conversations”
A founder can handle customer, investor, and team messages from the supported surfaces while carrying forward relevant commitments between replies.
“Revising a prepared answer by voice”
When a suggested reply has the wrong time or outcome, the user can hold fn and state the change, then review the revised text before inserting it.
Frequently Asked Questions
Which apps and platforms does Chalked support?
Chalked is a Mac app for Apple silicon. Prepared replies currently work in Gmail and LinkedIn in Safari or Chrome. English Messages support requires macOS 26.
Does Chalked send messages automatically?
No. Tab inserts a suggestion at your cursor, and you can edit it, ignore it, or send it yourself.
Do I have to talk to use Chalked?
No. Chalked prepares replies quietly and shows them when ready. Voice through the fn key is an optional way to change the intended outcome.
What does Chalked remember?
It can retain sourced commitments and working context that may improve later replies. Captured items keep their source and status and can be inspected, corrected, exported, or removed.
How does Chalked handle conversation access and privacy?
The site says Chalked reads a bounded current conversation through Accessibility, without screenshots or screen recording. Private mode keeps reply context on the Mac. Private on-device replies require macOS 26 and Apple Intelligence.
Quick Facts
- Category
- Mac reply assistant
- Platform
- Apple silicon Mac
- Supported replies
- Gmail and LinkedIn in Safari or Chrome
- Messages support
- English Messages on macOS 26
- Minimum prepared-reply OS
- macOS 15+
- Interaction
- Tab inserts; fn changes the intended outcome
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