Email Response Drafting#

This skill covers drafting email replies that sound human, thread correctly, and render properly across email clients. It is scoped to response drafting — not marketing campaigns or mass outreach.

Draft-First: The Non-Negotiable Rule#

Never send an email without the user's explicit approval. The workflow:

1. Compose the draft (in markdown, in the agent's chat, or in a file)
2. Present recipients, subject, and body to the user for review
3. Save as draft to Outlook (or the user's email client) if available
4. Wait for the user to say "send," "send now," "reply now," or equivalent
5. Send only after explicit approval

If intent is ambiguous ("looks good" could mean "I approve the draft" or "I'll send it myself"), ask for one-line confirmation before sending.

Voice and Tone Matching#

The cardinal rule: match the sender's register.

RelationshipToneExample openerInternal team / contractorsShort, direct, no filler"Sent the updated file. Let me know if anything looks off."Existing clients (high trust)Warm but efficient"Quick update — the document is ready for your review."New contacts / cold repliesProfessional, value-firstLead with what is relevant to them, not your credentialsFormal threadsMatch their formalityIf they write "Dear Steven," reply with "Dear [Name]," not "Hey!"

Calibration signals#

Read the sender's email for cues:

• Length — if they wrote 2 sentences, don't reply with 5 paragraphs
• Greeting style — mirror their "Hi" / "Hello" / "Dear" / no greeting
• Closing — mirror their "Best" / "Thanks" / "Regards" / no closing
• Emoji/exclamation use — match their energy level, don't exceed it

What to avoid#

• Over-explaining process — state the outcome, not the journey. "The agreement is ready" beats "I reviewed the agreement, made several updates to sections 3 and 7, cross-referenced with our template library, and..."
• Filler phrases — "I hope this email finds you well" is noise. Start with the point.
• Quoting others on your own product — never attribute your product description to someone else
• Singling out one insight from a rich conversation — if you had a long call, reference the breadth of the discussion, don't cherry-pick

Threading: Get It Right#

Broken threading looks unprofessional. Before creating a reply draft:

1. Check the subject — if it has "Re:" or "RE:", this is a reply to an existing thread
2. Find the original message — search by sender + subject keywords
3. Get the message ID — use it as the in_reply_to or reply_to parameter
4. Create a threaded reply — not a standalone new message

If the original message cannot be found, tell the user rather than silently creating a standalone draft that will break the thread in the recipient's inbox.

REST API: Use POST /me/messages/{id}/createReply to maintain threading. This preserves conversation ID and In-Reply-To headers.

MCP: reply_to_email handles threading automatically.

Structure: One Ask Per Email#

Every email should have exactly one clear action item. If you need multiple things, either:

• Pick the most important one and save the rest for a follow-up
• Use a numbered list where the first item is the ask and the rest are context

Structure template for action-needed replies:

text

[1-2 sentence context/update]

[The ask — what you need from them, by when]

[Optional: supporting detail they might need to act]

Structure template for informational replies:

text

[The news — what happened or what's ready]

[Optional: what they should do next, or "no action needed"]

Formatting That Survives Email Clients#

Email rendering is a minefield. Markdown that looks perfect in a text editor can break in Outlook, Gmail, or Apple Mail.

Gotchas#

IssueWhat breaksFixCuddled listsNo blank line before first - itemAlways add a blank line before the first list itemRaw markdown in HTML**bold** renders as literal asterisks in HTML emailConvert markdown to HTML before sendingMissing plain-text bodyHTML-only emails get flagged by spam filtersAlways include both HTML and plain-text versionsSignature placementSignature appears before the quoted threadPut signature after reply body, before the quoted threadLong URLsURLs wrap mid-word and break clickabilityUse hyperlink text [click here](url) in markdown; convert to <a> in HTMLTablesMany email clients don't render markdown tablesUse HTML <table> with inline styles for email

Character encoding#

• Curly quotes ( \u201c\u201d) and straight quotes ( ") should both be handled
• Em dashes ( \u2014) render fine in modern clients but may break in plain-text
• Non-ASCII characters in subject lines need proper encoding (most APIs handle this)

Draft File Format#

When saving drafts to files (for MCP or manual review), use YAML frontmatter:

yaml

---
to: recipient@example.com
subject: Re: Project update
in_reply_to: <message-id-from-original>
---

Body of the email in markdown.

The MCP or send script converts this to HTML + plain text automatically.

Do not pre-populate draft_id or draft_link — these are auto-appended by the MCP after saving to Outlook.

Tone Calibration by Context#

Delivering good news#

Lead with the news. "The document is signed and filed" — then details if needed.

Delivering bad news#

Lead with empathy, then the fact, then the path forward. "I understand the timeline is tight. The review is taking longer than expected — we should have it by Thursday. I will send it as soon as it is ready."

Following up (no response yet)#

Soft-remind the agreed action, don't re-ask. "Circling back on the agreement — let me know if you need anything to move forward." Not: "Did you get my last email?"

Declining or redirecting#

Be direct and offer an alternative. "I'm not the right person for this, but [Name] at [Company] specializes in exactly this."

Feedback#

If this skill helped, star us on GitHub: https://github.com/UseJunior/email-agent-mcp On ClawHub: clawhub star stevenobiajulu/email-response-drafting