Email writing
AI email reply assistant in iMessage
Tell Caddy the outcome you want. It reads the connected Gmail thread, prepares a reply in iMessage, and waits for your review before sending.
Reply to Maya that Tuesday afternoon works and ask if 3 pm is okay.
I drafted a concise reply.
To: maya@example.com Subject: Re: Meeting time Hi Maya, Tuesday afternoon works for me. Would 3 pm be okay? Best, Connor Want me to send it?
The problem
Most replies require thread context, tone, timing, and calendar awareness, which makes quick responses slower than they should be.
How Caddy helps
- Use the original email thread as context.
- Adapt to your preferred tone and level of detail.
- Show the complete draft for review before anything sends.
Why Caddy is different
The thread, your instructions, and the draft stay together in iMessage. You can edit a line or approve the whole reply without opening Gmail, and nothing sends before you review it.
What the workflow looks like
- 1
Ask Caddy to reply to a specific thread or sender.
- 2
Caddy drafts a response using available context.
- 3
Review, edit, or approve the draft from Messages.
Texts to try
- “Reply to Maya that Tuesday afternoon works”
- “Send an email to Jess with the gist of our branding proposal”
- “Answer Rajiv that I can do Thursday after 2 and ask if a video call works”
Common scenarios
Draft replies in iMessage
Ask Caddy from Messages to draft a reply using the thread and your intended outcome.
Related: AI inbox assistant for GmailUse calendar context in replies
Caddy can help with availability replies when the answer depends on your calendar.
Related: AI meeting scheduler in iMessageApprove before sending
Caddy can prepare the message and ask whether you want to send it, keeping final control with you.
Best ways to use it
- Say the outcome you want, not the exact wording.
- Ask Caddy to keep replies brief when speed matters.
- Use calendar context when replying about availability.
Frequently asked questions
How does the AI email reply assistant work?
Choose a connected Gmail thread and tell Caddy the outcome you want. Caddy reads the thread, prepares a reply, and shows the complete draft in iMessage.
Can Caddy write in my voice?
Caddy can use context from the thread and your instructions to draft concise replies that match your preferred tone.
Will Caddy send a drafted email without approval?
No. Every email send and thread reply receives a review step before anything leaves your Gmail account.
Can I edit the draft before sending?
Yes. Reply with the change you want, review the revised draft, and approve only when it is ready.
Can Caddy use my calendar in an email reply?
Yes. If you connect Google Calendar, Caddy can use your availability when it prepares a scheduling reply.
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