Email drafting improvements: greeting personalization, recipient/subject prompts, and smart defaults

Summary

When drafting emails through the email agent, Claude should be smarter about greetings, recipients, and subjects to reduce back-and-forth.

Current Issues

1. "Hi All" interpretation: When user says "draft an email to 'Hi All'" Claude searches for an existing email instead of asking for recipients
2. Raw URLs: URLs in email drafts show as full paths instead of hyperlinked text
3. Greeting logic: Doesn't adapt greeting based on number of recipients
4. Missing recipient handling: Should have a clear prompt pattern when recipient isn't specified
5. Missing subject handling: Should have a clear prompt pattern when subject isn't specified

Proposed Improvements

1. Greeting Personalization

• Multiple recipients (to: field): Use "Hi All" or list names ("Hi Alexandra, Stephen, Rosie, and Mary")
• Single recipient: Use person's name ("Hi Alexandra")
• No recipients yet: Skip greeting or use placeholder

2. Smart Hyperlinks

When user provides URLs in their message, automatically embed them as clickable text instead of showing raw URLs.

Example:

• User says: "Here's the agenda: https://docs.google.com/document/d/abc123"
• Draft should show: "Here's the agenda"

3. Recipient Prompt Pattern

When user doesn't specify recipient:

• Ask: "Do you have a recipient in mind, or should I leave it blank for now?"
• Don't block on this, offer to draft with placeholder

4. Subject Prompt Pattern

When user doesn't specify subject:

• Ask: "Do you have a subject in mind, or would you like me to suggest a few?"
• Offer 3 suggestions so user can reply:
• 1 (use first suggestion)
• 2 (use second suggestion)
• 3 (use third suggestion)
• blank (leave subject empty)
• more (generate 3 more suggestions)
• Or write a custom subject directly

5. "Hi All" Context Detection

When user says something like "draft an email to 'Hi All'" or "let 'Hi All' know", recognize this as needing recipient specification, not an email search.

Example Flow

User: "Draft an email about the meeting"

Claude: "Got it! A few questions:

1. Recipients: Who should I send this to? (or reply 'blank' to fill in later)
2. Subject: Here are 3 suggestions:

• 1: Meeting Follow-up
• 2: Today's Meeting Notes
• 3: Action Items from Meeting

Reply with 1/2/3, 'blank', 'more', or write your own subject."

User: "stephen@beachhutpr.com, rosie@beachhutpr.com" and "1"

Claude: [Drafts email with "Hi Stephen and Rosie," and subject "Meeting Follow-up"]

Benefits

• Fewer clarifying messages back and forth
• More natural conversation flow
• User stays in control with clear options
• Handles mobile/Telegram use case (quick replies like "1", "2", "blank")

Context

This feedback came from real usage via Telegram bot where the user was on mobile and wanted quick, efficient email drafting with minimal back-and-forth.