Email Send Direct

Send a single email via Gmail API from CLI

When to use

• "write an email to X"
• "send email to Y"
• "reply to the email"
• Any single email sending (not mass campaign)

IMPORTANT: Confirmation rule

ALWAYS first --dry-run, show preview to the user, and only after "yes" send without --dry-run.

Composing Guidelines

Before writing a single word:

1. Read the full thread — inbox AND sent, not just the latest message. Use email-read skill to pull last 3-5 days of correspondence with this contact.
2. Check CRM — read leads.csv and people.csv for context: deal stage, last activity, relationship notes. The email must reflect where we actually are, not where we were a week ago.
3. Identify what they asked — list every question or request from their last message. Each one must be answered.

Writing rules:

• Answer their questions first. Don't open with pleasantries or context-setting. If they asked "can you invoice monthly?" — start with "Yes, we'll submit monthly invoices."
• Match the thread tone. If the conversation is casual ("Hey Ivan"), reply casual. If formal ("Dear Mr. Pasichnyk"), reply formal. Mirror their level.
• No bot language. Never write: "Please find attached", "I hope this email finds you well", "As per our conversation", "Don't hesitate to reach out". Write like a human.
• No unnecessary bullet points or formatting. Business emails are paragraphs. Use bullets only when listing 3+ distinct items that genuinely benefit from a list.
• Reference shared context. Use "as discussed", "as you mentioned", "following up on our call" — shows you're in the conversation, not generating from a template.
• Keep it short. 3-5 sentences for a reply. 2-3 short paragraphs max for a proposal email. If you need more, the content belongs in an attachment.
• One clear call-to-action. End with exactly one thing you want them to do: review, sign, reply, schedule.

Ivan's voice:

• Short, concrete, direct
• Professional but warm — not stiff, not overly casual
• Says "we" for company actions, "I" for personal commitments
• Signs off: "Best," or "Thanks," — never "Best regards," or "Sincerely,"
• First email in thread: "Hi [Name]," — replies: often no greeting, just jumps in

Anti-patterns (never do these):

Paths

How to run

Simple email

cd $GOOGLE_TOOLS_PATH
.venv/bin/python3 send_email.py \
    --to user@example.com \
    --subject "Subject" \
    --body "Message text" \
    --dry-run

With CC

.venv/bin/python3 send_email.py \
    --to user@example.com \
    --cc other@example.com \
    --cc another@example.com \
    --subject "Subject" \
    --body "Message" \
    --dry-run

With attachment

.venv/bin/python3 send_email.py \
    --to user@example.com \
    --subject "NDA attached" \
    --body "Please find attached." \
    --attach /path/to/file.pdf \
    --attach /path/to/another.pdf \
    --dry-run

Reply in thread (search by query)

.venv/bin/python3 send_email.py \
    --to user@example.com \
    --subject "Re: Original Subject" \
    --body "Reply text" \
    --reply-to 'from:user@example.com subject:"Original Subject"' \
    --dry-run

Reply in thread (by message ID)

.venv/bin/python3 send_email.py \
    --to user@example.com \
    --subject "Re: Original Subject" \
    --body "Reply text" \
    --reply-to-id MESSAGE_ID \
    --dry-run

Body from file

.venv/bin/python3 send_email.py \
    --to user@example.com \
    --subject "Subject" \
    --body-file /path/to/message.txt \
    --dry-run

Parameters

*Either --body or --body-file is required.

Workflow for Claude

1. Prepare the email text
2. Run with --dry-run
3. Show preview to the user
4. After confirmation -- run WITHOUT --dry-run
5. Script automatically verifies sending (labels, snippet)

Output

Dry-run

============================================================
  EMAIL PREVIEW
============================================================
  From:    Your Name <your@email.com>
  To:      user@example.com
  Cc:      other@example.com
  Subject: Re: Topic
  Thread:  abc123 (reply)
  Attach:  file.pdf (23,794 bytes)
------------------------------------------------------------
Message body here...
============================================================

[DRY RUN] Email not sent.

After send

  Sent! Message ID: 19c90af2b9ceaf61

  Verify:  OK
  ID:      19c90af2b9ceaf61
  To:      user@example.com
  Cc:      other@example.com
  Subject: Re: Topic
  Labels:  ['SENT']
  Snippet: Message body here...
  Attach:  ['file.pdf']

Sender

From: Your Name <your@email.com>

Troubleshooting

Related skills

• email-send-bulk -- mass sending via Google Sheets
• email-read -- reading email
• email-monitor -- automatic monitoring
• google-auth -- if authorization issues