Email Send Direct Skill

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:

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.
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.
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):

| Bad | Why | Instead | |-----|-----|---------| | "Please find attached the proposal" | Corporate robot | "Proposal is attached" or "Attached is the proposal we discussed" | | Bullet-point summary of what's attached | They can read it themselves | One sentence saying what it is | | Repeating info they already know | Wastes their time | Reference it briefly, move forward | | "Let me know if you have any questions" | Empty filler | Specific CTA: "Let me know if the terms work" | | Long intro before answering their question | Buries the answer | Answer first, context after |

Paths

| What | Path | |------|------| | Script | $GOOGLE_TOOLS_PATH/send_email.py | | Token | $GOOGLE_TOOLS_PATH/token.json | | venv | $GOOGLE_TOOLS_PATH/.venv/bin/python3 |

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

| Parameter | Description | Required | |-----------|-------------|----------| | --to EMAIL | Recipient (can specify multiple) | yes | | --cc EMAIL | CC (can specify multiple) | no | | --subject TEXT | Email subject | yes | | --body TEXT | Email body text | yes* | | --body-file FILE | Body text from file | yes* | | --attach FILE | Attachment (can specify multiple) | no | | --reply-to QUERY | Gmail query for thread lookup | no | | --reply-to-id ID | Gmail message ID for reply | no | | --dry-run | Preview only, do not send | no |

*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

| Problem | Solution | |---------|----------| | 401 Unauthorized | Refresh token: google-auth skill | | Attachment not found | Check file path | | Thread not found | Check --reply-to query | | Encoding issues | Body is automatically UTF-8 |

Related skills

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

Agent Skills: Email Send Direct

Install this agent skill to your local

Skill Files