Email

Email

Draft and send emails with contact context and tone matching. Looks up the recipient first, selects the right tone based on the relationship, and always CCs you.

Connectors

Connector	Required	Purpose
Google Workspace	Yes	Gmail (send, search, reply), Contacts (lookup), Drive (share files)

Examples below show gws CLI syntax, but the workflow works with any Google Workspace connector. Claude will adapt the API calls for your setup.

Sending Models

There are two ways to set up email sending:

Model	How it works	Best for
AI assistant account (default)	Sends from a dedicated AI email address, CCs you on everything	Transparency — recipients see it came from your AI assistant
Your own account	Sends directly from your personal email	When you want emails to appear as if you wrote them yourself

This skill is designed around the AI assistant account model — it CCs you on every email so you always see what was sent on your behalf. If you switch to sending from your own account, you may want to remove the CC behavior.

Configuration

Load env.md for accounts (send-from address, CC address). Load style-guide.md for tone and voice.

From env.md:

• Sending account (the email address emails are sent from)
• CC address (your personal email — so you always see what was sent)

From style-guide.md:

• Tone by relationship type
• Voice and sign-off conventions
• Formatting rules

Workflow

Step 1: Identify Recipient

Look up the recipient in your contacts:

1. Search contacts — by first name, last name, or email prefix (full names often fail in search)
2. If found: Pull email, relationship type, and any notes for personalization
3. If not found: Ask the user for the email and relationship context

Step 2: Gather Intent

• What's the purpose? (Update, request, thank you, intro, etc.)
• Key points to include?
• Any specific tone override?

If the user gave enough context in their initial message, skip to drafting.

Step 3: Draft

Select tone based on relationship:

Relationship	Tone	Characteristics
Personal/Family	Warm, genuine	Express real interest, comfortable with emotion
Close Friends	Casual, playful	Direct and unfiltered
Professional	Polished but approachable	Clear, warm but efficient
Formal/External	Professional, clear	Structured, appropriate formality

Structure:

Subject: [Clear, specific]

<p>[Greeting],</p>
<p>[Main point — get to it quickly]</p>
<p>[Supporting context if needed]</p>
<p>[Closing / next step]</p>

<p>[Sign-off],<br>
[Your name or AI name]</p>

Step 4: Review

Present the draft for review:

To: [recipient]
CC: [your CC address]
Subject: [subject]

[Body preview]

Ready to send? (Yes / Edit / Cancel)

Wait for confirmation before sending. Never send without explicit approval.

Step 5: Send

Send via your email connector:

gws gmail +send \
  --to "[email protected]" \
  --cc "[email protected]" \
  --subject "Subject line" \
  --body "<p>HTML body content</p>" \
  --html

Confirm: "Sent! [Subject] to [Name] — you're CC'd."

Reply Mode

When replying to an existing conversation instead of starting new:

1. Find the thread — search for the most recent message from the recipient
2. Get message details — for threading headers (Message-ID, Thread-ID)
3. Send the reply — using your connector's reply method (handles threading automatically)

Sharing Files

When an email needs to include a document:

1. Upload to Drive
2. Share with recipient (reader access)
3. Include the Drive link in the email body

Error Handling

Scenario	Response
Contact not found	Ask for email and relationship context
Auth expired	Re-authenticate, retry once
Send fails	Report the error — don't retry silently

Customization Notes

How to adapt this skill to your own setup.

• Voice — Edit style-guide.md to match your writing voice. The tone-by-relationship table is the most important thing to personalize.
• Sending model — See "Sending Models" above. If switching to send from your own account, update the sending address in env.md and consider removing the CC.
• CC behavior — The default CCs you on everything because emails come from the AI assistant account. If sending from your own account, you can remove the CC.
• HTML vs plain text — This defaults to HTML for better mobile display. Switch to plain text if your recipients prefer it.
• Contact lookup — If you don't use Google Contacts, replace Step 1 with whatever contact store you use (local files, CRM, etc.)