MailtoChat user manual

Getting started

MailtoChat is a small menu bar app. It reads the email you have selected in Apple Mail and pastes it into Claude Desktop, in the chat or project you choose.

Allow two permissions

macOS asks you to approve two things the first time you use the app. Without them MailtoChat cannot do its job.

• Automation (Mail). Lets MailtoChat read the email you have selected in Apple Mail.
• Accessibility. Lets MailtoChat find your chat in Claude Desktop and paste into it. The General settings show whether it is granted.

Sending an email

1. In Apple Mail, click the email you want to send. It can be from any account.
2. Press an action shortcut, or click the MailtoChat icon in the menu bar and choose an action.
3. MailtoChat finds the route that matches the email and opens the right chat in Claude Desktop.
4. The email, its details and its attachments are pasted in. If the action has a prompt and auto-send is on, it is submitted.

Chat routes

A route says: when an email matches this, put it in that place in Claude. Routes keep the context of a client, team or topic in one chat or project, and stop your sidebar filling with one-off chats.

Add a route

Open Routes in the app and choose Add Route. Each route has these parts:

• When an email is... Choose Sent to (To) for mail you send, or Received from (From) for mail you receive. A route checks one field.
• Who it applies to. Choose Anyone at a domain, which also covers its subdomains, or One email address.
• ...put it in Claude. Choose Send it to: an existing chat, a new chat in a project, a new chat, or an incognito chat.
• Standing instructions (optional). A line added to every email on this route, such as “Always reply formally, in Dutch.”

The Result line at the bottom of the window restates the route in plain words, so you can check it before saving.

Which route wins

• A full email address beats a domain.
• Between routes of the same kind, the one higher in the list wins. Drag routes to reorder them.
• Use Test your routes to type an address and see which route applies, and why.

When no route matches

A window asks where the email should go. Choose a place, then pick one of three buttons:

• Save stores your choice as a new route.
• Just This Once uses it for this email only.
• Cancel sends nothing.

If you would rather not be asked, untick Ask where to send emails that have no route in the settings, or tick Don’t ask again in the window. Unrouted emails then go to a new chat.

Prompts and shortcuts

MailtoChat has six action slots. Each one has a name, a shortcut and a mode.

Two modes

• Paste the email only. The email goes into the chat and nothing else.
• Add a prompt to the email. Your prompt is placed above the email. The route’s standing instructions follow.

Make your own actions

The two custom slots stay out of the menu until you give them a name and a prompt. Write the instruction you keep retyping, such as “Extract the name, company and request and add them as a row in my leads spreadsheet.” Anything Claude can do with an email can be an action.

Send automatically, or review first

With Send to Claude automatically on, actions with a prompt are submitted right after pasting. Turn it off to read the prompt first and press send yourself. Paste Only never submits.

What gets sent

• The email. Sender, recipients, date, subject and body.
• Attachments. Every attachment goes along, whatever its type. Tiny images under 15 KB, such as logos and signature graphics, are skipped.
• Temporary files. Attachments are copied to a temporary location that only your user can open. They are removed after sending or on failure, and anything older than an hour is swept when the app launches.
• Your clipboard. MailtoChat pastes on your behalf and then restores what you had copied.

Activity log

The Activity tab lists what you sent and where. It is plain text, stored on your Mac, and searchable. Click a subject to open the email in Mail, or click the route to jump to its chat in Claude. You can clear the log or switch it off.

General settings

• Send to Claude automatically. Whether prompts are submitted straight after pasting.
• Ask where to send emails that have no route. Turn off to always open a new chat for unrouted mail.
• Wait for Claude to load a chat. A slider for how long MailtoChat waits after opening a chat before pasting. The default is 1.5 seconds. If emails land before the chat has loaded, raise it.
• Accessibility status. Shows whether the permission is granted.

License and updates

MailtoChat is free during the launch period. Your license key lives in the License & Privacy tab. Once a week the app checks for updates and confirms your license. Usage analytics are optional and shown as a choice in the same tab.

Privacy

MailtoChat never sends your emails, attachments or prompts to us. They travel from Apple Mail to Claude Desktop on your Mac. The only things that leave your Mac through MailtoChat are the weekly update and license check, plus optional analytics if you choose to share them. Once an email is in Claude, it is handled under Claude’s own terms, as if you had pasted it yourself.

Troubleshooting

Still stuck? Contact support at [SUPPORT EMAIL].